Usher

Remember the ’90s? If you do, here’s some news that might make you feel old: We’ve been in the 2000s for a quarter century now.

That’s a long time, and over these past 25 years, the world has changed a lot. So, too, has the music that helps give it color. With the speed of the modern music industry, we’ve already had several musical eras, each yielding era-defining hits in their own ways.

Perhaps the best way (the way we thought would be best, anyway) to crystallize and digest this sprawling, diverse epoch is to look back over these last 25 years of music, pick out the 100 best hits, rank them, and explain what makes each one iconic.

That’s just what we’ve done.

The rules here are pretty straightforward: to qualify for the list, the song had to have reached the top 10 on the Billboard Hot 100. Hundreds of songs accomplished this over the last 25 years, and many of them are great, far more than fit on this list. Lasting impact, long-term listenability, and our team’s taste level all factored into the choices. And, before you start yelling about the century begining in 2001, we’re using the popular perception of centuries (beginning in 2000), not the strict construction where the century begins in 2001.

Here are the best hit singles of the last 25 years.

100. Mark Ronson — “Uptown Funk” Feat. Bruno Mars (2015)

Like many songs on this list, Mark Ronson and Bruno Mars’ “Uptown Funk” was a smash hit that you couldn’t go anywhere without hearing. Even in the comfort of your own home, the song would come blaring out of a speaker attached to your TV or a passing car. The song was so good and so universal that it eventually got really tiring and exhausting to hear and endure in a few months. However, with over 5 billion views on the video and so many more plays across streaming platforms, there’s no denying it as one of the biggest hits and most widely beloved songs of the past quarter century. – Wongo Okon

99. Gwen Stefani — “Hollaback Girl” (2005)

Nearly 20 years ago, Gwen Stefani made it impossible to spell “B-A-N-A-N-A-S” without melodically chanting it. “Hollaback Girl” became Stefani’s first (and only) No. 1 on the Billboard Hot 100 — establishing her icon status outside of No Doubt. More importantly, it endures as an empowering anthem with endless lore. The Neptunes produced it. Pharrell, a frequent and fruitful Stefani collaborator, co-wrote it — later citing Naomi Campbell as inspiration. Stefani more or less confirmed she wrote “Hollaback Girl” as a roundabout clapback to Courtney Love insulting her. May “this my sh*t” ring eternal. – Megan Armstrong

98. Nicki Minaj — “Super Bass” (2011)

Today, Nicki Minaj is established as one of hip-hop’s most successful stars, and you could say it all started with her first major hit, “Super Bass.” Minaj is a rapper, but “Super Bass” was a real pop gem. The era-defining hit was a perfect bridge between those two worlds and a terrific showcase of Minaj’s skillset: It’s a radio-ready earworm that’s also carried by Minaj’s uncommonly dexterous flow. – Derrick Rossignol

97. Black Eyed Peas — “I Gotta Feeling” (2009)

Black Eyed Peas absolutely dominated the late 2000s decade with a slew of hit records. Among these records is arguably their best release with “I Gotta Feeling.” The diamond-certified track was the second single from the group’s fifth album, The E.N.D., and it went on to be a seemingly impenetrable mainstay on the singles chart. “I Gotta Feeling” spent 14 weeks atop the Billboard Hot 100, in addition to snagging a Grammy Award for Best Pop Performance By A Duo Or Group With Vocals in 2010. “I Gotta Feeling” also exemplifies the rising trend in electro-pop rap that was inescapable in the music world in the early 2010s to the chagrin of some rap purists. – W.O.

96. B.o.B — “Nothin’ On You” Feat. Bruno Mars (2010)

If the only thing this catchy bop had going for it was introducing the world to the singular genre-bending, generation-bridging talents of musical maestro Bruno Mars (and the Smeezingtons, the production collective responsible for other smashes like Wiz Khalifa’s “Young, Wild & Free” and Cee-Lo’s “F*ck You”), it’d belong on this list. But it also shifted the mantle of hip-hop, demarking the moment when those pesky “blog rappers” truly became viable hitmakers at the highest level. Nominated for three Grammys, including Record Of The Year, it’s a cheesily unforgettable ode to true love. – Aaron Williams

95. Michael Jackson — “You Rock My World” (2001)

Though Michael Jackson’s dominance as a solo act took place in the 1980s and ’90s, his otherworldly superstar status and talents helped him showcase more flashes of immense success even after his peak. The lead single from Jackson’s 2001 album Invincible, the last album he released before his death in 2009, “You Rock My World” was truly a blast from the past. Showing off vintage Mike, it peaked at No. 10 on the Billboard Hot 100 chart — his first song to do so in six years. It earned a Grammy nomination the following year, Jackson’s first since 1997. Despite what critics had to say at the time of its release, “You Rock My World” is nothing short of exquisite, beautifully crafted, and captivating — words that still applied even after Jackson’s legendary career allegedly fell off. – W.O.

94. Roddy Ricch — “The Box” (2020)

The first No. 1 of 2020, “The Box” launched the “TikTok trend to massive playlist hit” pipeline that the industry still can’t seem to free itself from. It’s an undeniably catchy song; the “windshield wiper” vocal at the beginning, the sinewy hook, the triumphant instrumental. It has all the fundamentals of a smash. But when it was paired with the ingenuity of bored teens on their phones, it became an industry-shifting juggernaut, the sort of song that defines careers, for better or worse. In Roddy’s case, it might be the latter, since everything he’ll do will be compared to “The Box.” On the other hand, it’s the kind of one-off hit that feeds generations, both figuratively and literally. I think he’ll live. – A.W.

93. Rema & Selena Gomez — “Calm Down” (2023)

Few songs capture the explosion of afrobeats’ popularity like Rema’s “Calm Down.” Prior to its remix with Selena Gomez, the song was a success in the afrobeats space, tallying a million daily streams at one point, but the remix took it to unimaginable peaks. In the weeks after its release, “Calm Down” would enter the Hot 100 chart and nearly make its way to the top, peaking at No. 3 and making it the most successful song in afrobeats history. “Calm Down”‘s success signaled Rema’s arrival as a new star at the forefront of afrobeats’ steady rise to household status. – W.O.

92. Alicia Keys — “No One” (2007)

Keys already had a few inescapably catchy records like this in her discography — “Fallin” and “If I Ain’t Got You,” to name a pair — but “No One” took it to a new level. The powerful ballad grew to be an unforgettable record from the 2000s, making Keys’ voice as ubiquitous as its repitious but effective chorus. “No One” spent five weeks at No. 1, grew to be the third most successful song of 2008 in the US, and it was the most-listened to song on the radio that same year. It was also the sixth most successful song of the 2000s decade in the US, and if that’s not enough, the diamond certification it received, as well as Grammy Awards wins for Best Female R&B Vocal Performance and Best R&B Song, should do the trick for you. In the end, “No One” is not only the most recognized record in Keys’ catalog, but one the most recognizable records from the 2000s. – W.O.

91. Psy — “Gangnam Style” (2012)

It was summer 2012 when one man in a tux and circle-shaped sunglasses named Psy made the world gallop on an imaginary horse and lasso for eight counts to his EDM-infused pop track “Gangnam Style.” The song was so powerful that its dance became a muscle reflex to many and encouraged flash mobs around the world. It also served as a cultural reset as it opened more doors for the world to familiarize themselves to a glimpse of K-pop, let alone Gangnam, one of the richest and lavish neighborhoods in Seoul, South Korea. The song became the highest K-pop song to chart on the Billboard Hot 100 during its time at No. 2 while dethroning Justin Bieber’s “Baby” as the most viewed YouTube video, and the first video on the internet to reach 1 and 2 billion views. – Lai Frances

90. The Kid Laroi — “Stay” Feat. Justin Bieber (2021)

The Kid Laroi and Justin Bieber’s “Stay” is undoubtedly one of a handful of songs that are probably inscribed in your brain from the pandemic years. The song was built for mainstream dominance — a pairing of one of music’s biggest stars with a social media breakout fave over roaring synths entwined into elements of electro, pop, and light rock. “Stay” was the type of earworm song meant to dominate the charts — and that it did, as the record spent four consecutive, and seven total, weeks atop the Hot 100 chart, making it the most dominant record in Laroi’s career and the second most in Bieber’s. – W.O.

89. Migos — “Bad And Boujee” Feat. Lil Uzi Vert (2017)

Another Metro Boomin masterwork, this captivating track brought the Migos to full mainstream acceptance. This No. 1 record topped the Billboard Hot 100 charts and is fueled by Offset’s terrific chorus and opening verse. – Elliott Wilson

88. Miley Cyrus — “Party In The USA” (2010)

Go ahead: I dare you to not sing along to the chorus to “Party In The USA” the next time it comes on in a bar. It’s impossible. Halfway through the first verse, you’ll have your hands up. It doesn’t matter that Miley Cyrus had “never heard a Jay-Z song” when she recorded it — “Party In The USA” is undeniable pop-rock perfection. Make it the new National Anthem. – Josh Kurp

87. The Weeknd — “Can’t Feel My Face” (2015)

Starting with his debut with the chilly House Of Balloons, The Weeknd had always been something of a known quantity in the scheme of the music scene. Recognized as one of the originators of the “PBR&B” sub-brand of the genre, his ghostly melodies had become emblematic of a certain kind of star — one who valued mystery over superstardom. Then the Canadian star dropped “Can’t Feel My Face,” totally upending his audience’s expectations. A complete 180-degree turn from his established lane, “Can’t Feel My Face” took The Weeknd from haunting, zonked-out navel gazing to burning up the dance floor. – A.W.

86. Rihanna — “Love On The Brain” (2017)

Rihanna’s latest album — ANTI, released in 2016 — birthed plenty of hit songs. While the steamy “Work” with Drake, the freeing “Needed Me,” and the daring and tempting “Kiss It Better” stand out, “Love On The Brain,” is the most unique moment on ANTI. The track is a swirling 1950s doo-wop tune reminiscent of Amy Winehouse, and one that showed Rihanna’s true vocal power. These qualities helped to make it the third most successful song on ANTI and the most recent multi-platinum single of Rihanna’s career. – W.O.

85. Usher — “OMG” Feat. Will.I.Am (2010)

Usher’s legendary career can be split into two halves, with his 2008 album Here I Stand being the median. The singer’s following album, 2010’s Raymond v. Raymond, transitioned Usher out of R&B superstardom and placed him firmly in pop glory, as exemplified by its third single, “OMG” with Will.I.Am. The anthemic pop record was a massive hit around the world and one that proved that Usher’s dominance could be maintained long after the Confessions days. – W.O.

84. Craig David — “7 Days” (2002)

Although I always knew that Craig David’s 2000 single was a huge hit, I had always thought it was very of its time, a marker of a moment. Sure, it helped popularize the then-burgeoning UK-based genres 2-step and garage (seemingly overnight), but only recently did I realize its lasting impact. When artistic successors as disparate as American rappers like Kyle and Korean pop stars like NewJeans ape your style — to say nothing of more-or-less direct musical offspring like the UK’s own PinkPantheress — it’s a sure sign that your work has resonated across oceans and generations alike. – A.W.

83. Outkast — “Hey Ya!” (2003)

OutKast’s fifth album, Speakerboxxx/The Love Below, spawned a pair of No. 1 records with “Hey Ya!” (an André 3000 solo track) and “The Way You Move” (a Big Boi solo track with Sleepy Brown). “Hey Ya!” would go on to sit at No. 1 for nine weeks and also serve as a preview into the genre-less approach André would take in the years that followed (see: New Blue Sun). After steering away from Outkast’s traditional music approach — which was already eclectic — Three Stacks delivered a record that has almost completely overshadowed the group’s musical legacy among a certain kind of fans. – W.O.

82. Fall Out Boy — “Sugar, We’re Goin Down” (2005)

The aughts saw many emo and emo-adjacent songs climb the charts, and most were just pop songs at heart. The years that followed Fall Out Boy’s emergence would just double down on this fact as they settled into jock jams, but let’s remember just how good their first widely heard bow was. Now considered a primary text of the genre, “Sugar, We’re Going Down” is sturdy and sweeping, an anthem that didn’t quite know what it was until after the fact, and whose esteem has only grown in time. – Philip Cosores

81. Beyoncé — “Break My Soul” (2022)

By the time Beyoncé released her Robin S.-inspired dance single “Break My Soul,” there had already been a renaissance (heh) of Black influence in electronic dance music — or perhaps a rebirth of love for EDM in Black culture. Either way, it felt like a homecoming of sorts — so, fittingly, of course, the moment required a Beyoncé co-sign to seal the deal. The runaway success of “Break My Soul,” with its intent to evoke early house music’s call to “release yourself” from the stressors of everyday life, solidified the resurgence of EDM’s originators, welcoming them home to the genre and the culture, and inviting them to extend their legacy. – A.W.

80. Lady Gaga — “Bad Romance” (2009)

Not long after playing in front of a few dozen people in the afternoon, Lady Gaga was ready for stadiums. “Bad Romance” improved on earlier singles “Just Dance” and “Poker Face” by making everything bigger — and more sordid. It’s the pop song equivalent of a German expressionist film. An earworm has never sounded so unnerving. Gaga wanted our ugly, our disease, but most of all, she wanted our love. “Bad Romance” ensured that she’ll always have it. – J.K.

79. T-Pain — “I’m Sprung” (2005)

First impressions matter the most. Fortunately for T-Pain, the Tallahassee Rappa Ternt Sanga chose to make one hell of a first impression. Splitting the difference between rapping and singing allowed him to tackle a topic atypical of most debuting rappers, with Pain finding true magic in the innovative use of the Auto-Tune audio plugin. While it had been in use for over a decade since the rise of digital audio workstations like Pro Tools, he pushed it past its intended pitch-matching purpose, using it as a makeshift vocoder. The rest is history. There may be those who wish he’d never popularized this use of the technology, but there are dozens of artists who owe their careers to his. – A.W.

78. Mario — “Let Me Love You” (2004)

This list wouldn’t be complete without a good dirty-macking anthem, and Mario had one of the best with his 2004 single “Let Me Love You.” His first line set the tone for the rest of the song as he sang, “Baby, I just don’t get it, do you enjoy bein’ hurt?” Music fans were enthralled with the song, as it peaked at No. 1 on the Hot 100 and stayed there for nine consecutive weeks. – W.O.

77. Taylor Swift — “You Belong With Me” (2009)

What’s the difference between a very good Taylor Swift song and a great Taylor Swift song? The bridge. “You Belong With Me” has one of her best (especially if you add the claps after “I’m the one who makes you laugh when you know you’re ’bout to cry”). The Fearless single demonstrated that Swift had greater ambitions than her country debut. She was ready to go from the bleachers to the big time. – J.K.

76. Paramore — “Ain’t It Fun” (2014)

Paramore is one of the more successful bands of the 2000s, making impact in both the rock world and the pop one. The band transcended its indie boundaries with “Ain’t It Fun,” reaching fans whose ties were mostly connected to other genres (the running joke about how much Black people love Paramore has existed for years). It’s their highest-charting single, peaking at No. 10 on the Hot 100 chart, and their second best-selling single behind “Misery Business.” – W.O.

75. Cardi B — “WAP” Feat. Megan Thee Stallion (2020)

Sexually explicit? Understatement. Ha! Fair to say, this dynamic duo brought us some joy during those tough Covid lockdown days. But still: Wash your mouths out with soap, ladies. – E.W.

74. Ed Sheeran and Justin Bieber — “I Don’t Care” (2019)

Ed Sheeran and Justin Bieber’s team-up was never the biggest song in the world and it’s hardly the most widely known of their catalog, but it remains an artistic high-water mark in both of their careers. The song tackles the social anxiety that both have been open about in a way that’s both breezy and direct, using assists from Max Martin, Shellback, and Fred Again.. for a bit of pop perfection that’s as good as anything they’ve ever done on their own. – P.C.

73. Disclosure and Sam Smith — “Latch” (2014)

Disclosure’s moment in the pop spotlight might have faded a bit over the last decade, but there is no denying the song that introduced the world to Sam Smith. Smith took the baton from the electronic duo and ran with it, making every first-time listener ask, “Whose voice is this?” Smith quickly headlined festivals, won Grammys, and then went through a much-needed complete artistic reinvention in the years that followed, but we can now be sure that “Latch” was not a flash in the pan for the singer, but a bold announcement of a career artist. – P.C.

72. Harry Styles — “As It Was” (2022)

“As It Was” was Harry Styles’ introduction to his house. Specifically, the bedroom. “As It Was” owes as much to ‘80s new wave as it does to bedroom-pop artists like Clairo. Styles sings softly and modestly about the necessity of embracing change (“In this world, it’s just us / You know it’s not the same as it was) before the song builds to a crescendo in the final moments. “As It Was” goes out on a high note. – J.K.

71. BTS — “Dynamite” (2020)

When the world needed them, they delivered. The all-English, feel-good, Jackson 5-esque, funk-pop track from BTS brought color and joy to the world during a time where everything seemed redundantly dull. As expected from one of the greatest boy groups of all time, “Dynamite” exploded to success shortly after its debut as it became BTS’ first No. 1 hit on the Billboard Hot 100 chart for three weeks; and the longest-charting song by a South Korean artist. That’s only a fraction of its accomplishments, but maybe most importantly, it became a signifier that K-pop could seamlessly cross into global markets, making the entire world feel a lot less small. – L.F.

70. Doja Cat — “Kiss Me More” Feat. SZA (2021)

Doja Cat’s peak pop stardom came with “Say So,” but right behind it was her SZA collaboration “Kiss Me More.” Doubling down on the sparkling pop-funk of “Say So,” it won multiple awards, like Best Pop Duo/Group Performance at the 2022 Grammys and Best Collaboration at the 2021 MTV VMAs. – W.O.

69. Justin Timberlake — “SexyBack” (2006)

Timberlake’s post-NSYNC solo career got off to a solid start with his debut album Justified and the top-5 single “Cry Me A River.” But, it was FutureSex/LoveSounds and “SexyBack” that made him a star. Both releases went No. 1 and showed that Timberlake could be a culture-defining icon on his own, outside of the ruthless ’90s and ’00s boyband machine that didn’t always produce big-time solo careers. Timberlake, though, banked on sexy, and the horny hit worked out, serving as a springboard for the multi-hyphenate career Timberlake continues to enjoy. – D.R.

68. Jimmy Eat World — “The Middle” (2002)

The world “emo” is synonymous in non-musical circles with behavior that is relentlessly downbeat, depressive, and self-absorbed. But how downbeat, depressive, and self-absorbed can you really be when you hail from Mesa, Arizona? The sunniness of Jimmy Eat World’s hometown can’t help but seep into their most famous song, in which Jim Adkins insists that “everything will be just fine” over pop-rock bouncy enough to soundtrack a local TV morning show. – Steven Hyden

67. Erykah Badu — “Bag Lady” (2000)

By the time Badu released “Bag Lady” from her second album, Mama’s Gun, “neo-soul” had been well established as a genre, but “Bag Lady” itself came to define what that genre sounded like — and what it meant. You can still hear echoes of its sonic formula in releases from some of today’s soul singers, including Ari Lennox and Summer Walker — albeit almost never as all-encompassing as Badu’s original take on ghetto spiritualism. Its sample of Soul Mann & The Brothers’ 1971 song “Bumpy’s Lament” remains one of the most recognizable, next to Dr. Dre’s “Xxplosive.” – A.W.

66. M.I.A. — “Paper Planes” (2008)

M.I.A. may have lost goodwill thanks to some of her controversial stances, but “Paper Planes” still feels untouchable. Her ascension from critical darling to festival headliner hinged on it, and some notable placements in film with Slumdog Millionaire and Pineapple Express (possibly the most 2008 movies ever made?) gave it the rocket boost it deserved. Of course, it is probably Diplo who rode the wave of this success longer, as this century is filled with successful projects he helped shape, but the fact remains that nobody quite sounded like M.I.A. before or since, and the world was cooler for it. – P.C.

65. Eve — “Let Me Blow Ya Mind” Feat. Gwen Stefani (2001)

What could have been. Although Eve’s initial production deal with Dr. Dre fell through when the Philly native was a teen, fans got to see a flash of an alternate reality in which Dre’s perfectionism never pissed off the “pitbull in a skirt” and she got to make the most of her sauntering, unrestrained flow. Tied with “Gangsta Lovin’” for Eve’s highest-charting single, it sparked the creative chemistry with Gwen Stefani that would see the two mavericks collaborate again on the latter’s “Rich Girl” in 2009. Told that “Let Me Blow Ya Mind” would never work, Eve promised to contradict such predictions, leading to a hit that truly lived up to its title. – A.W.

64. Usher — “Confessions Part II” (2004)

There’s no way this list exists without a song from Usher’s fourth album, Confessions. In the second of two title tracks, Usher confesses to cheating on his partner and impregnating another woman with the hope that he’s forgiven for his actions. It had people hooked, so much so that the song became Usher’s sixth No. 1 record (one of the four Confessions yielded) while also reaching triple-platinum status. – W.O.

63. Sabrina Carpenter — “Espresso” (2024)

2024 will be remembered as the year of Sabrina Carpenter. Short N’ Sweet is the best pop album of the year (fight me), the “Nonsense” outro overtook the internet, and Carpenter opened on part of Taylor Swift’s The Eras Tour. But, appropriately, “Espresso” caffeinated Carpenter’s pop ubiquity. Carpenter always had a knack for clever, effective (fun and flirty) hooks. “That’s that me espresso” reigns supreme until further notice. – M.A.

62. Hozier — “Take Me To Church” (2013)

Before “Too Sweet” became a hit this year, Hozier was the “Take Me To Church” guy. The song was a bit of an unusual mainstream hit, a slow, moody, soul- and gospel-inspired number that’s well-written and well-performed, but doesn’t exactly follow the formula of a career-launching success. Indeed, though, that’s what it became and it remains a signature hit of the early 2010s. – D.R.

61. Lil Baby and Gunna — “Drip Too Hard” (2018)

It’s rare that a song can literally launch two careers at the same damn time. These masterful melody makers joined forces early and haven’t looked back since. New generation of ATLiens. – E.W.

60. Zach Bryan — “I Remember Everything” Feat. Kacey Musgraves (2023)

Zach Bryan has become a bit of a chart mainstay in the last few years, but one of his biggest songs had the privilege of giving Kacey Musgraves her first No. 1 song. The song is an instant-classic duet that finds the soothing voice of Musgraves a natural fit for Bryan’s emotionally direct delivery. As artists, they underscore country’s crossover appeal, where popularity and quality don’t have to be mutually exclusive. – P.C.

59. Missy Elliott — “Work It” (2002)

It’s sort of astonishing that there wasn’t immediately a string of radio hits released in the wake of “Work It” that used reversed vocals on their choruses. If this song were released today, there absolutely would be. But then again, if it were released today, it would still sound every bit as futuristic as it did on the day it was released in 2002. The song is a testament to the creativity of its creator, Missy Elliott, who repurposed the hip-hop staples of her youth, fusing them with out-of-this world production from longtime collaborator Timbaland, and crafted a song that would soundtrack the next 20 years — and more. – A.W.

58. Jay-Z — “Empire State Of Mind” Feat. Alicia Keys (2010)

Sorry Sinatra, Jigga crafted a new Big Apple anthem. With wild boasts, “I made the Yankee hat more famous than a Yankee can” and a wailing chorus from Ms. Keys, the record gave Jay his first No. 1 single as lead artist. – E.W.

57. Silk Sonic (Bruno Mars and Anderson .Paak) — “Leave The Door Open” (2021)

Just the idea of Bruno Mars and Anderson .Paak joining forces sounded like a dream of musical compatibility. Indeed, it very much was: Their styles came together perfectly on the throwback soul of their debut single as Silk Sonic, “Leave The Door Open.” .Paak wasn’t wrong when he said recently, “I think that I have a gift of bringing the best out of other people.” – D.R.

56. Kendrick Lamar — “Humble” (2017)

Kendrick Lamar’s first-ever No. 1 hit was a revelation as much for what it didn’t do as for what it did. What it didn’t: Significantly revamp the Compton rapper’s sound or fury, sticking resolutely to his formula of music with a message — even when he was making obvious bids for radio play, such as “Swimming Pools.” What it did do: Begin tipping the balance of rap’s focus from party-ready club bops back toward street-stomping declarations of intent. It would take another seven years for him to complete the shift, but “Humble” laid the foundation for “Not Like Us” to overthrow Drake’s reign. – A.W.

55. Shakira — “Hips Don’t Lie” Feat. Wyclef Jean (2006)

Shakira secured her place in pop history in 2006 with a song that’s become one of her signature hits. The Colombian icon teamed up with Wyclef Jean for the irresistible “Hips Don’t Lie” from her Oral Fixation, Vol. 2 album. Shakira harnessed the power of her ability to translate her seductive lyrics through her body, namely her hips. The cross-cultural collaboration hitting No. 1 on the Billboard Hot 100 chart was a major milestone for Latin music in the mainstream. – Lucas Villa

54. 50 Cent — “P.I.M.P.” Feat. Snoop Dogg (2003)

50 Cent seems to be far removed from music, yet his debut album, Get Rich or Die Tryin’, continues to impact today’s rap. Among the bevy of critically acclaimed tracks is the “P.I.M.P.” remix with Snoop Dogg, which in recent days has been pushed to the side. As a sonic departure from his cult classics, “P.I.M.P.” provided a look into another side of street life on a reggae soundbed while mending the long strained East Coast/West Coast musician relationship. Long before the red pill community ran YouTube, 50 Cent provided them with a theme song to sip a fruity drink to. – Flisadam Pointer

53. Drake — “In My Feelings” (2018)

By the time Drake’s fifth album Scorpion dropped in the summer of 2018, the Toronto rapper was a worldwide superstar and an undeniable hitmaker. With pre-release singles “God’s Plan” and “Nice For What” tearing up the charts, “In My Feelings” shot out of a cannon as the third No. 1 song from the album and Drake’s fourth overall chart-topper. “In My Feelings” got a significant boost from the dance challenge that accompanied it and one created by viral internet personality Shiggy. As with most successful dance challenges, fans from near and far took part in the fun and there was no looking back for Drake and “In My Feelings.” – W.O.

52. Snoop Dogg — “Drop It Like It’s Hot” Feat. Pharrell (2004)

Of course, Snoop Dogg’s first-ever No. 1 hit was a Pharrell (by way of The Neptunes) production. But not just any Pharrell production; it could very well be The Neptunes’ most innovative, left-field creation ever — and with a catalog that includes Clipse’s “Grindin’,” that’s saying A LOT. “Drop It Like It’s Hot” pushed the boundaries of West Coast rap, pop radio, and fans’ perceptions of Pharrell, the consummate hookman turned supremely confident rapper in his own right. As Pharrell and Chad admitted in the Lego biopic Piece By Piece, the two Virginians were higher than they’d ever been when they crafted this beat, thanks to the Snoop effect. Their music reached new heights, too. – A.W.

51. Carly Rae Jepsen — “Call Me Maybe” (2012)

“Call Me Maybe” is a song about love at first sight. It was love at first listen when the world heard “Call Me Maybe,” which still sounds just as fun and carefree as it did when it was a viral sensation. It’s one of Canada’s greatest contributions to culture, along with Jim Carrey and insulin. Don’t you dare call Carly Rae Jepsen a one-hit-wonder, however: “Call Me Maybe” was followed by the best pop album of the 2010s. – J.K.

50. Megan Thee Stallion –“Savage” Feat. Beyoncé (2020)

2020 was the year viral TikTok hits became Billboard chart toppers. While “Old Town Road” had previously made the jump from TikTok trend to the top of the chart, 2020 had a string of trending sounds on TikTok ride the “air traffic controller dance” wave to the No. 1 spot. “Savage” was one of those, but it was distinguished by a handful of distinctive traits. After a prolonged duel with Doja Cat’s “Say So” (which it supplanted with its ascension), “Savage” proved Megan Thee Stallion’s staying power. Beyoncé added a timely assist (and made OnlyFans go mainstream), but it was fans’ belief in Meg that drove her and “Savage” to their status as fixtures of pop culture. – A.W.

49. Billie Eilish — “Birds Of A Feather” (2024)

How is “Bad Guy” not Billie Eilish’s entry on this list? Fair question. Also, fairly simple answer. “Birds Of A Feather” is Eilish’s purest pop song in her acclaimed discography. It doesn’t hurt that it’s also probably her most purely romantic love song — or that it asserted there’s nothing she isn’t willing to try in the name of vulnerability. She can execute mesmerizing hushed vocals better than anyone, and she can nail an emotional belt to high heavens? (Eilish told Apple Music’s Zane Lowe this vocal is “the highest I’ve ever belted in my life.”) Unfair. – M.A.

48. Icona Pop — “I Love It” Feat. Charli XCX (2013)

What if I were to tell you that before Brat, Charli XCX had a whole career, filled with numerous hits, both written for others and herself? It’s easy to forget that as Charli’s 2024 moment feels so massive, but there was a time when “I Love It” inhabited a similar hip intersection between pop and indie. Icona Pop might not have done much else of note since, but Charli’s trademark wit and attitude was on full display from the jump, and she never looked back. – P.C.

47. Adele — “Rolling In The Deep” (2011)

Prior to “Rolling In The Deep,” Adele had already had some well-received and enjoyable singles from her debut album, 19. But with the release of 21 and its mega-hit lead single, she went from “rising star” to “supernova,” turning into a sales juggernaut whose second album reigned on the Billboard 200 for 24 weeks. “Rolling In The Deep” offers a microcosm to explain why; Adele’s warm, soulful vocals evoked a bygone era, her songwriting belied a timeless spirit (“she’s been here before,” as the old folks say), and yet, she was relatably down-to-earth, with struggles as universal as core human experiences. She really did have it all. – A.W.

46. Taylor Swift — “Blank Space” (2014)

“Shake It Off” might be the most widely known Taylor Swift song, but its follow-up single was the song that proved the successful transition away from country to pop was complete, and a success. “Blank Space” found Swift working with Max Martin and Shellback on a tune that played into her own romantic reputation, proving that her clever lyrics can be just as effective over arena-ready pop production as they were with an acoustic guitar in hand. It’s pop songwriting at its best, and set the bar for Swift’s future endeavors incredibly high. – P.C.

45. Rihanna — “Umbrella” Feat. Jay-Z (2008)

To understand Rihanna’s present-day stardom is to understand how “Umbrella” created limitless horizons for her career. Serving as the lead single of Good Girl Gone Bad, Rihanna’s second No. 1 single of her career, and her lone diamond-certified record, “Umbrella” started the shift described by the album’s title, prompting the world to view Rihanna less as the girl next door and more as the musical badass she’s become since, demonstraction ability to tackle grungy, rock-influenced production, which we’d see her do with later albums like Rated R and Talk That Talk. – W.O.

44. Cardi B, Bad Bunny, and J Balvin — “I Like It” (2018)

In my review of Cardi B’s game-changing 2018 debut album Invasion Of Privacy, I called “I Like It” “a moment that forms the centerpiece of not just Cardi B’s album, but also Cardi B’s identity.” It’s the most original-sounding song on the album, tapping into a unique fusion of old-school party rap and 1960s boogaloo (before that term was frustratingly co-opted by the group that seems most ideologically removed from the genre’s main audience) that represented the disparate parts of Cardi’s heritage and her influences. Its sample of Pete Rodriguez’s “I Like It Like That” set it at the center of cultures, genres, and generations, making its dominance at No. 1 no surprise. – A.W.

43. Kanye West — “Stronger” (2007)

Kanye West’s name stirs up a mix of emotions. But both his recorded and produced contributions to music cannot be discredited. With “Stronger,” Ye dove head first into electronic, a path other rappers have since traveled down. Genre-switching is always a tricky space for acts to navigate. But not everyone is Ye. The genius of “Stronger” is that West didn’t have to forgo anything creatively. Instead, he forced it to meet him where he was. Sandwiched between “Can’t Tell Me Nothing” and “Good Life,” Ye demonstrated that his mind knows no bounds. – F.P.

42. Jay-Z — “Izzo (H.O.V.A.)” (2001)

This lead single from Jay-Z’s The Blueprint cemented Hov’s status as hip-hop’s leader. Over a Kanye West flip of The Jackson 5’s classic “I Want You Back,” Mr. Carter asserts, “Can’t leave rap alone / The game needs me.” – E.W.

41. Ludacris — “Move Bitch” Feat. Mystikal and I-20 (2002)

Before it was an impromptu and somewhat incongruous protest song against a certain tangerine-hued would-be fascist, it was an Atlanta club fight song demonstrating Luda’s penchant for catchy hooks, boisterous beats, and combative concepts. Not every part of it has aged so well — I-20’s fortunes have turned, and Mystikal’s have gone even worse — but it’s a classic snapshot of a moment in time when the energy of rap music was more pugnacious than perked-out, and rap stars were larger-than-life. – A.W.

40. Tyla — “Water” (2023)

The success of afrobeats in the past few years also brought more attention to other genres of African music, like amapiano. The South African-based genre received worldwide recognition thanks to the viral success of Tyla’s “Water.” The track made a splash among fans who helped make it become a top-10 hit on the Hot 100, a viral hit thanks to its TikTok dance, and a Grammy-winning record after it was honored at the 2024 awards. The attention amapiano receives in future years will forever be connected to the success of “Water.” Now talk about impact. – W.O.

39. SZA — “Snooze” (2022)

In the era where many claimed that “R&B is dead” (it’s not), SZA proved that it was alive and well with her 2022 record “Snooze.” Housed on her long-awaited sophomore album SOS, “Snooze” was not the immediate breakout hit from the album (that would be “Kill Bill”) but to many, it was the album’s best record from the jump. Eventually, “Snooze” took the throne as the lead hit from SOS and it’s remained there ever since. – W.O.

38. Destiny’s Child — “Say My Name” (2000)

Destiny’s Child is one of the greatest girl groups of all time. But the member swap-out (and introduction of Michelle Williams) controversy, the attention was on everything but DC’s music. Then, they dropped the video for “Say My Name.” As legend goes, Beyoncé wasn’t a fan of the first mix, but with a few tweaks, the now-legendary track turned the record into a blueprint for dozens of groups (FLO, for example) to follow. With crisp harmonies, infectious blends, deeply expressive storytelling, and cross genre appeal, Destiny’s Child solidified their spot in the history books and Beyoncé as a vocal force with a leading lady aura. – F.P.

37. Outkast — “The Way You Move” Feat. Sleepy Brown (2004)

So, the more popular of the two signature singles from Outkast’s historical double album Speakerboxxx/The Love Below is undoubtedly André 3000’s “Hey Ya!” from the more melodic half of the project. But among hip-hop heads, the indisputably better single was his partner Big Boi’s “I Like The Way You Move,” a sprawling, soulful update of the Atlanta duo’s classic sound. Over the course of the song, Big Boi lays rumors of the group’s demise to rest (prematurely, as it turns out) before extolling their trademark virtue: that B-A-S-S, bass. – A.W.

36. The Weeknd – “Blinding Lights” (2020)

Max Martin has written and produced some of the most successful pop songs of all time. He’s as omnipresent on the charts as McDonald’s is to highway exits. Martin’s masterwork, his Big Mac, as it were: “Blinding Lights.” The Weeknd’s impeccably smooth mega-hit from 2020’s After Hours was named the greatest Hot 100 song of all-time by Billboard. It’s also the most-streamed track in Spotify history. It’s not always the case that a singer’s biggest song is also their best, but it happened with “Blinding Lights.” – J.K.

35. Justin Timberlake — “Mirrors” (2013)

By the time the 2010s rolled around, Justin Timberlake was a global megastar thanks to an acting career that picked up in the late 2000s. However, Timberlake came roaring back in 2013 with the release of his third album, The 20/20 Experience. The project sold over 900,000 copies in its first week and gave the world “Mirrors,” a record that would prove to be one of Timberlake’s last moments atop the pop charts. “Mirrors” bleeds for love just as much as it pours a beautifully welded combination of R&B, rock, and more onto the ears of listeners. Timberlake’s music career birthed numerous classic, and “Mirrors” is undoubtedly one of them, but also one of the records that best stood the test of time. – W.O.

34. Daft Punk — “Get Lucky” Feat. Pharrell Williams (2013)

When this song came out, everybody loved it immediately. Then we heard it 100,000 times and everybody got sick of it. Then some time passed and everybody started to love it again. It’s now illegal in most states to DJ a wedding and not play “Get Lucky” at least once. It’s the rare song that works whether you’re 8 or 88. – S.H.

33. Justin Bieber — “Sorry” (2015)

Purpose was Justin Bieber’s line of demarcation between teenybop and big-boy pop. (This is not to speak ill of Journals, a shamefully underrated pop/R&B EP.) “Love Yourself,” “Sorry,” and “What Do You Mean?” each hit No. 1 on the Hot 100, but “Sorry” consumed pop culture. Was Bieber singing about Selena Gomez or apologizing for his then-poor public image? Nobody knew, and nobody cared once that trumpet hit. The official music video netted over 3.8 billion views, and Bieber performing that “Sorry” choreography in manufactured rain to close every Purpose World Tour show was equally iconic. – M.A.

32. Doja Cat — “Say So” (2020)

Doja Cat infamously derided “Say So” as an obvious bid for radio, but I think this was as much a ploy to distance her from its dominance ahead of her sound shift as it was a true commentary on her feelings for the track. It’s fair that she got a little sick of it over the course of the pandemic year after performing it to so many empty venues due to COVID, but she simply can’t deny that it was her first time truly taking music seriously. Even she wasn’t prepared for its extended chokehold over pop culture; perhaps her later reaction was just fear of her own ability to craft infectious, inescapable grooves. – A.W.

31. Chappell Roan — “Good Luck, Babe!” (2024)

2024 was the year of Chappell Roan, even though she only released one new song. It just happened to be her best. “Good Luck, Babe!” is about a closeted woman who refuses to embrace her feelings for Roan, and women in general. “You’d have to stop the world just to stop the feeling,” Roan sings with theatricality over a synthy beat. “Good luck, babe.” No one needs to wish Roan good luck: she’s doing just fine as is. – J.K.

30. Juice WRLD — “Lucid Dreams” (2018)

Juice WRLD’s discography could single-handedly explain the necessity for Grammy Awards’ Best Melodic Rap Performance category. Whether the late musician was indeed a rapper is an argument for another day, but what isn’t up for debate is Juice WRLD proving hip-hop is not a monolith. Breaking through the flashy, uptempo, cocky tunes of the time, Juice WRLD’s raw vulnerability on “Lucid Dreams” fostered yet another emo-rap staple birthed out of SoundCloud rap’s independent movement (lawsuits be damned). – F.P.

29. Dua Lipa — “Levitating” (2021)

If you had to pick a contemporary song to replace “Soul Bossa Nova” during the opening credits of Austin Powers: International Man Of Mystery, you could do a lot worse than Dua Lipa’s “Levitating.” The mega-hit from Future Nostalgia (an album partially inspired by Mike Myers’ British spy character) is pure disco jubilation. The hand claps! The “woo”s! The way Dua Lipa says “sugarboo”! “Levitating” sounds like falling in love. In other words: it’s shagadelic, baby. – J.K.

28. Beyoncé — “Crazy In Love” Feat. Jay-Z (2003)

“Crazy In Love” is best acknowledged as the record that put Beyoncé’s solo career in full swing. The lead single from her debut album Dangerously In Love, “Crazy In Love” was a riveting combination of pop, R&B, soul, and funk that reinforced the range within Beyoncé’s artistry and proved that she would indeed be a superstar in the music world. Two decades later, we’ve seen that to be beyond true, but it all took off with “Crazy In Love,” which also helped to give Beyoncé the first Grammy wins of her solo career. – W.O.

27. Nelly — “Country Grammar (Hot Shit)” (2000)

The Midwest has something to say, and Nelly kicked off St. Louis’ mainstream rap conversation. His debut single “Country Grammar (Hot Shit)” accomplished what very few others have done since: thoroughly introduce himself, propel a region forward, and temporarily weaken the East and West Coasts’ stronghold on gangster rap. All of that makes Nelly a certified legend in the game. Plus, you probably haven’t been able to listen to a nursery rhyme the same ever since. – F.P.

26. Olivia Rodrigo — “Good 4 U” (2021)

There’s a lot of reasons why “Good 4 U” is special: the opening bass line, the electric chorus, the fact that Paramore’s Hayley Williams and Josh Farro got paid a whole lot of money for the song’s (dubious) similarity to “Misery Business.” But the main reason is Olivia Rodrigo’s fiery theater kid rage. She provided a pop-punk anthem for High School Musical (and High School Musical: The Musical: The Series) fans, and for that, we thank you. – J.K.

25. Jay-Z — “Dirt Off Your Shoulder” (2004)

While The Black Album didn’t turn out to be the swan song it was billed as, the intent behind it certainly drove some of Jay-Z’s greatest creative output. Jay wanted it to be mythic in its scope and tone, and it largely succeeded — especially on the front end — but “Dirt Off Your Shoulder” was the grounding the album needed to truly shine. Jay’s biggest hits are usually club bangers and singalong anthems, and here, he manages to make something that incorporates the best of both without coming off cloying. He flexes on us, but invites us to flex too; “If you feeling like a pimp, n****, go on, brush your shoulders off / Ladies is pimps, too.” It’s probably the most inclusive club hit in hip-hop. – A.W.

24. Post Malone and Swae Lee — “Sunflower” (2019)

It’s an odd quirk of the 21st century streaming era that some of the biggest hits of the last half-decade or so have hailed from the soundtracks of animated films. But while most of them have expectedly appeared on albums accompanying Disney properties (think Frozen, Encanto, etc.), “Sunflower” was instead a Marvel production — ironically, the part of Marvel not owned by Disney. “Sunflower,” from Spider-Man: Into The Spider-Verse, combined two of the most successful new voices in pop music, a lilting chorus evocative of tentative young love, and one of the best-known superheroes in the universe to make one-of-a-kind magic. – A.W.

23. Future — “Mask Off” (2017)

With Metro Boomin behind the boards providing one of hip-hop’s illest samples, Future gets vulnerable with lyrics about addiction and a haunting chorus that you can’t get out of your head. – E.W.

22. Drake — “Hold On, We’re Going Home” Feat. Majid Jordan (2013)

Drake’s ability to mine both international mini-genres and disparate waves of American pop music history ought to be studied. Call him a “culture vulture” if you want, but when he locks in the way he did on this spin on 1980s New Wave, he is one of music’s most undeniably compelling creators. In 2013, the idea of this sort of revivalist bent was still largely relegated to the most nostalgic corners of Tumblr. Give the man credit where it’s due, he does his research — and in 2013, he touched heaven. – A.W.

21. Coldplay — “Viva La Vida” (2008)

There’s a reason why Chris Martin and Co. are one of the few 21st century bands that stand with the most streamed acts in the world. It’s because of bangers like “Viva La Vida” — nearly 2.4 billion spins and counting on Spotify — that emphatically demand to be played in the largest stadiums and in front of the biggest audiences who sing along to every word. – S.H.

20. Bad Bunny — “Me Porto Bonito” Feat. Chencho Corleone (2021)

Bad Bunny paid tribute to the music of the Caribbean with his 2023 album Un Verano Sin Ti. The Puerto Rican superstar pushed reggaeton into the future with the alluring “Me Porto Bonito.” As a nod to the genre’s past, he teamed up with ex-Plan B member Chencho Corleone. Bad Bunny bridged the gap between reggaeton fans old and new with his freaky club banger. At the same time, he permeated the pop mainstream when the song peaked No. 6 on the Billboard Hot 100 chart. – L.V.

19. Lil Jon & The Eastside Boyz — “Get Low” Feat. Ying Yang Twins (2003)

If you were to tell me 20 years ago that the best club song of the early aughts would also be used in the 2024 Democratic National Convention as Georgia declared its support of Harris/Walz… well, I might actually believe it, considering one of the candidates is named Walz. But still, it is a song as beloved for its unabashed dirtiness as its many hooky line deliveries, and it hasn’t gone out of style since its chart-dominating release. – P.C.

18. Travis Scott — “Sicko Mode” (2018)

Scott’s sonic explosion is like three songs in one. Anchored by an uncredited Drake performance where he disses on-again, off-again rival, Kanye West. “Lost my respect / You are not a threat.” – E.W.

17. 50 Cent — “In Da Club” (2003)

Nothing captured the star power of 50 Cent in the early 2000s like “In Da Club.” The Get Rich Or Die Tryin standout certified that 50 Cent would at least be a superstar in the rap game in the years going forward. What actually happened is it gave 50 Cent worldwide fame and recognition and became one of the most easily recognized songs in rap history. Few have reached the towering status of “In Da Club,” which is now diamond-certified, one of only a handful of rap songs to reach that status. – W.O.

16. Cardi B — “Bodak Yellow” (2017)

The journey from reality show personality to certified superstar began with one of hip-hop’s most massive major label debut singles. “These expensive, these is red bottoms, these is bloody shoes.” Cardi’s career takeoff hit diamond status and instantly her stripper days were over. – E.W.

15. Luis Fonsi and Daddy Yankee — “Despacito” Feat. Justin Bieber (2017)

Two veterans in Latin music joined forces in 2017 to make history. Puerto Rican pop star Luis Fonsi teamed up with reggaeton pioneer Daddy Yankee for the sultry “Despacito.” Fonsi’s song about making love later caught the attention of Justin Bieber, who sang in Spanish on the remix. The combined forces of Fonsi, Daddy Yankee, and Bieber catapulted “Despacito” to the top of the Billboard Hot 100 chart for 16 consecutive weeks. Since then, many more songs in Spanish have flooded the pop charts. – L.V.

14. ASAP Rocky — “Fuckin’ Problems” Feat. Drake, 2 Chainz, and Kendrick Lamar (2013)

It’s a blog era explosion as hip-hop’s new generation came together for this infectious party-ready posse cut. Oddly enough, it’s a raunchy refrain from Kendrick Lamar that’s most remembered here. – E.W.

13. Lorde — “Team” (2014)

Most people remember Lorde’s launch with “Royals,” but the truth is that the follow-up single from her now-classic debut packs deeper emotional resonance while feeling in tune with her still-developing identity as an artist. “Team” isn’t just a great Lorde song, but it’s one of the most dynamic and long-lasting pop tunes to ever chart high in Billboard, an anthem for the teen in all of us, then and now. – P.C.

12. Ariana Grande — “Thank U, Next” (2018)

Ariana Grande cemented her superstardom with the release of her 2018 single “Thank U, Next.” The record was the lead single from her fifth album of the same title, and one that was aided by her breakup with then-fiancé Pete Davidson. “Thank U, Next” was met by immediate praise and acclaim by fans and critics who were enamored by Grande’s daring approach, as she name-dropped her celebrity ex-boyfriends in reflection on past relationships. – W.O.

11. Outkast — “Ms. Jackson” (2001)

Prior to the release of “Ms. Jackson,” Outkast were a known quantity, a fixture on rap radio, certified hitmakers in the world of hip-hop. “Ms. Jackson” is arguably the moment they crossed over, becoming what their Atlanta compatriots might jokingly call “white famous.” The second single from the duo’s fourth album, Stankonia, it became Big Boi and André 3000’s first No. 1 single, and technically saved the rollout for Stankonia after the commercial failure of lead single “B.O.B.” The song was even beloved by Erykah Badu’s mother, who partially inspired it; Badu joked on the Rap Radar podcast, “Baby, she bought herself a ‘Ms. Jackson’ license plate.” – A.W.

10. Kendrick Lamar — “Not Like Us” (2024)

The lyrical knockout shot heard round the world. This is the soundtrack to Kendrick’s victory lap over Drake. It’s a diss song and a hit song. See y’all at the Big Game. – E.W.

9. Usher — “Yeah!” Feat. Lil Jon and Ludacris (2004)

Part of what made Usher’s collaboration with Lil Jon and Ludacris such a hit was the element of surprise, something that we don’t get much in today’s SEO-oriented, algo-gaming climate of hit optimization. Even at the height of Lil Jon mania, no one could have predicted the smooth Usher, of all people, would tap the rough-edged crunk club bop of the hotly demanded producer — or that the combination would work so well. Even weirder? We never got a Lil Jon/Luda connection without Usher (they teamed up again on Jon’s Crunk Juice cut “Lovers And Friends” later that year). “Greater than the sum of its parts” feels like an understatement where “Yeah!” is concerned. – A.W.

8. Eminem — “Lose Yourself” (2002)

“Lose Yourself” is perhaps Eminem’s signature song, which is saying a lot considering how many hits Em has amassed over his lengthy career. It was groundbreaking, really, both for Eminem personally and for hip-hop as a whole: It was his first No. 1 single and the first rap song to win the Academy Award for Best Original Song. The biggest sign of the track’s continued impact? Eminem is still making money from the “mom’s spaghetti” lyric. – D.R.

7. The Killers — “Mr. Brightside” (2005)

Nick Valensi once lamented that his band The Strokes never got as big as the bands they inspired. “Our songs are better than ‘Mr. Brightside,’” he says in the oral history Meet Me In The Bathroom, “How come that’s the one everyone is listening to?’” Well Nick — to paraphrase The Social Network — if you could have written “Mr. Brightside,” you would have written “Mr. Brightside.” – S.H.

6. Lil Uzi Vert — “XO Tour Llif3” (2017)

Lil Uzi Vert’s breakthrough arrived at a pivotal time in rap. The transition away from archaic gatekeeping channels to the ushering in of a new subgenre (hello, “SoundCloud rap” era), Lil Uzi Vert’s magical track “XO Tour Llif3” proved that the kids are OK. Rap is a reflection of the times, and Lil Uzi Vert’s “XO Tour Llif3” embodies that — fluid, alternative, emotive, and dramatic, hence the birth of emo rap. Lil Uzi Vert is a true trendsetter, and it all started with “XO Tour Llif3.” Should Lil Uzi Vert truly retire, their contribution to hip-hop is etched in stone. – F.P.

5. Britney Spears — “Toxic” (2004)

“Toxic” is the kind of pop song that even people who don’t “like” pop music have to admit is great. It also helped resurrect Britney Spears’ career. It was her first top-10 hit in four years (since “Oops!… I Did It Again”), a remarkable achievement for a song built around high-pitched strings and an old Bollywood sample. It was nice of Britney to honor her pop star predecessor Madonna by making “Me Against The Music” the first single from In The Zone, but come on, it really should have been “Toxic.” – J.K.

4. Lil Wayne — “A Milli” (2008)

Weezy has an extensive catalog that proves he’s one of hip-hop’s greatest artists but this Bangladesh-produced banger remains his shining moment. “Who that said they gon’ beat Lil Wayne?” – E.W.

3. Taylor Swift — “All Too Well (Taylor’s Version)” (2021)

“All Too Well” is Taylor Swift’s masterpiece. Inspired by a breakup with a certain scarf-straling actor (allegedly), the power ballad from 2012’s Red was a fan favorite before becoming everyone’s favorite when the 10-minute version was released on Red (Taylor’s Version). It’s the longest No. 1 hit in Hot 100 history and an emotional centerpiece of The Eras Tour. But “All Too Well” doesn’t just mean a lot to Swifties; it’s a song close enough to Swift’s heart that she made her filmmaking debut with All Too Well: The Short Film. You’ll remember it all too well. – J.K.

2. Kanye West — “All Falls Down” Feat. Syleena Johnson (2004)

When people say they miss the “old Kanye,” this is what they mean. The version of the mercurial rapper-producer we’ve got now is so far removed from the humble, message-minded everyman the Windy City MC started out as, that it’s bizarre to imagine they’re even the same person. But Kanye never would have had so much faith from fans that he could call himself a god were it not for the quiet relatability inherent in admitting, “I’m so self-conscious / That’s why you always see me with at least one of my watches.” It was unusual for a rapper to confess such a thing at the time, and even more so that he would have the charm, humor, and wit to pull it off. – A.W.

1. Beyoncé — “Single Ladies (Put A Ring On It)” (2008)

Beyoncé will probably never release Renaissance and Cowboy Carter visuals, but we’ll always have the “Single Ladies (Put A Ring On It)” video. Beyoncé, Ebony Williams, Ashley Everett, and their leotards didn’t need a TikTok algorithm to turn JaQuel Knight’s “Single Ladies” choreography into a global phenomenon. The perpetual No. 1 single from Beyoncé’s third solo LP, I Am… Sasha Fierce introduced Sasha Fierce as Beyoncé’s alter ego, even though she didn’t need to employ an alter ego. Her presence (or aura, if you will) alone was enough to shatter pop-cultural paradigms. (The ripple effects included Kanye West and Taylor Swift’s infamous 2009 MTV VMAs catastrophe.) In 2024, Beyoncé remains restless in her drive to artistically reinvent — conquering country, directing a record-breaking concert film, et al. “Single Ladies” showcased Beyoncé’s crystalized vision in its simplest form and cemented her inevitability. – M.A.

will.i.am is an investor and Chief Visionary Officer at Uproxx Studios.