Rick Ross

To truly understand the works, legacy, and longevity of William Leonard Roberts — better known as Rick Ross — it helps to consider the work he released under his first rap name, Teflon Da Don. Once upon a time, the portly Carol City, Miami rapper popped up on Erick Sermon’s Def Squad Presents Erick Onasis under his former title, delivering a solid, if unmemorable, verse that laid the groundwork for what his on-wax persona would eventually become.

The reason this verse — the context of it as well as the content — is so instructive is that it tells us who Rick Ross is right away. The fact that he’s on an Erick Sermon record illuminates a deep and abiding love and respect for the craft and history of hip-hop. The fact that he wisely rejiggered his polished delivery to something more resonant to the streets for which he wanted to speak highlights his gift for transformation. And discarding the generic Teflon Da Don for the eye-catching Rick Ross shows he knows the importance of committing to the bit.

He’s committed to the bit for just about 15 years now — an accomplishment that would have been unheard of around the time he got his start (although his one-time mentor Sermon was getting close at the time). But behind the gimmick is a deeply considerate, master craftsman who can’t help but refine and sharpen his skills and the tools of his trade any chance he gets. In another lifetime, Rick Ross is a guy who still shows up to every cipher, eager to demonstrate his latest batch of improvements, an MC’s MC, just having fun with it while he can.

That’s why he’s been so good for so long, why he’s earned the respect and friendship of the top artists in the business, and why, no matter how tired of the bit we can all claim to be, his career shows no signs of slowing up just yet. Here are Rick Ross’ best songs from his massive — and still growing — catalog.

32. “Here I Am” Feat. Avery Storm, Nelly

Admittedly, the first time I played this back to record my thoughts about it, I was taken aback at Avery Storm’s chorus. It’s so twangy and his pronunciation of “her” made me burst out laughing. Was this really what we all listened to in my twenties? … Well, yeah. And it rode at the time, too. If you were picking up your girl for a date, you didn’t want to pull up listening to R&B — you’d look soft. But she would probably be turned off by all that gangsta stuff. You’d go home sad, that’s for sure. Songs like this offered a comforting middle ground before the “soft boy” agenda (and its accompanying “sophistiratchet” movement for the ladies) blurred the lines between these stifling binaries. It might play like The Flintstones now, 14 years later, but nostalgia is a helluva drug, and I’m bopping along like I’m 25 all over again. — Aaron Williams

31. “Nobody’s Favorite” Feat. Gunplay

2019’s Port Of Miami 2 was an incredibly solid work that somehow went unremarked upon by the rap world at large. Perhaps Rozay titling it after his debut album nearly 20 years after that album was initially released left some fans unsure about the project. Was he going backward? Would he try to update the sound that made him a Southern trap figurehead so long ago? The answer to both was “no.” Although it wasn’t by leaps and bounds, the album saw Ross embrace further evolution. And while much of it got overlooked in the rush of projects that marked its release year, it’s impossible to ignore the reunion between Rick and one of his staunchest (and wildest) soldiers, Gunplay. “Nobody’s Favorite” is a nihilistic standout that ironically became many fans’ favorite from the sequel project, with Ross flashing glimmers of his grimy past and Gunplay stealing the show as always. — A.W.

30. “Richer Than I Ever Been”

The title track from Ross’s latest release oozes both smooth, athletic cool, and lurking, tightly coiled menace. Over a stripped-down piano loop — which somehow sounds every bit as lush as some of the most boisterous compositions he’s rapped on — Ross delivers a hypnotic hook that harkens back to his first major hit. Katt Williams once joked that “Hustlin’” could make a listener feel like a baller even while stocking groceries. In that same way, “richer than I ever been” is like an affirmation, an incantation, and a manifestation all rolled into one. You might not be able to relate now, but it makes you feel like you will. — A.W.

29. “Magnificent” Feat. John Legend

Confession time: This one is for the ladies. You know who you are. A relic of the time when this was a legit business practice in the recording industry (along with the “club record,” the “street anthem,” and other colorful archetypes that eventually became redundant in the streaming era), this track is kind of a blatant overture to the portion of the listening public that prefers R&B and slow jams to the roughneck rap Ross usually traffics in (no pun intended). But although he became way more proficient at incorporating those aesthetics into his usual fare on later material, this Trilla standout was a fantastic example of the form and holds up. — A.W.

28. “Not For Nothing” Feat. Anderson .Paak

The lilting slack guitar and console organ are something of a change for Ross — not a big, splashy lane switch, more of a subtle trajectory shift — that somehow promises just as much road ahead of him as behind. It suggests that there are modes we still haven’t heard from him and that he’s willing to challenge himself to find them. Sure, the lyrical content is well-trod territory for Rozay, but you can make anything sound fresh with just minor adjustments. Case in point: This song, also employs a slick, smoky chorus from Anderson .Paak, with whom Ricky is developing some intriguing chemistry. — A.W.

27. “Gold Roses” Feat. Drake

Rick Ross and Drake make a great team (their collaborations are neck-and-neck with Ross’ Jay-Z team-ups). Ross lends a veneer of… if not “credibility,” then at least “feasibility” to Drake’s Sopranos-style braggadocio. And Drake’s admittedly sharply pointed pen game certainly lights a similar fire in Ross. “Gold Roses” lives more in Drake’s wheelhouse, sonically, but Rozay’s comfort level over the muted, trilling sample is a testament to his understated chameleonic tendencies. He often becomes exactly what the song needs, but getting to hear him out of his element, so to speak, highlights just how good at it he really is. — A.W.

26. “Amsterdam”

Production separates good rappers from great tastemakers. The Cardiak-produced “Amsterdam” is fine tastemaking. How Ross rhymes his way around the Cortex sample is like watching Usher Raymond rollerskate: Suave, self-assured, moving in a motion that enchants. A slight but effective addition is the Teedra Moses vocals. They whisper in the background as if a part of the beat, too reserved to distract, but essential to the ambiance. How well the “Barry Gordy of the streets” is able to coexist between loud, brassy anthems and atmospheric, quiet storm contemplation is why his catalog will be regarded highly for years to come. With fans pointing to “Amsterdam” as a premium deep cut. — Yoh Phillips

25. “911”

Where some rappers struggle with their identity, Ross knew that his music was to promote choruses for corner boys, hymns for hustlers, mantras for manifesters, and sutras for street pharmacists. “911” conveys all those ideas in a single explosive track overflowing with juggernaut energy and lionhearted exuberance. Of all his trap classics, “911” sounds made to make the listener feel bulletproof. A song that boils with the reckless vigor of a rapper audacious enough to call an album God Forgives, I Don’t. But that is why he is so compelling: Ross sells a character who gambles in a world where only the strong survive and risks get rewarded. “911” is strength and risk-taking personified. — Y.P.

24. “Maybach Music 2” Feat. Kanye West, Lil Wayne, T-Pain

As with any sequel, expectations were higher than the average record for “Maybach Music 2.” Swapping Jay-Z for T-Pain, Lil Wayne, and Kanye West was a good call in 2009 when all three artists were in stride, burning up Billboard and torching every song they touched, qualifying their appearance on the “Maybach Music” follow-up. Together they assemble like the 2017 Golden State Warriors, a super team with enough primetime talent to be a championship franchise. And although the features changed in future editions, “Maybach Music 2” solidified what the series would become: A gathering of greatness to make songs in the key of opulence, luxury, and splendor. — Y.P.

23. “Rapper Estates” Feat. Benny The Butcher

A truly astonishing amount of Ross’s best stuff is, surprisingly, on his last album, 2021’s Richer Than I Ever Been. Unrestrained by the commercial demands of most major-label releases (Epic gives him a thrilling degree of free reign), The Boss gets to indulge his rapper’s-rappers impulses, resulting in a project packed to the brim with the sort of rhymes he’d have reeled off in his Teflon days. He’s only gotten more proficient over time, tapping one of the heavyweight bar-focused lyricists of the modern age in Benny The Butcher and hanging with him line for line. This is the Ross I’d wanted to hear ever since he changed his rhyme-de-plume in the mid-2000s. — A.W.

22. “Foreclosures”

Rap allowed Rick Ross to cultivate an image of a money-making businessman with a mogul mind and empire-building ambitions. “Foreclosures,” a 2015 deep cut, adds depth to that character by critiquing financial irresponsibility. Prior to its release, 50 Cent filed for personal bankruptcy, a possible source of inspiration for why “Foreclosures” is a lyrical lashing against living beyond your means. Even if the motivation was a petty shot at an adversary’s misfortune, there is timeless validity in the overall message: Success is a precious jewel that won’t stay in your possession if it’s mismanaged. Look no further than Sam Bankman-Fried as a modern example of what happens when you don’t act your wage. — Y.P.

21. “3 Kings” Feat. Dr. Dre, Jay-Z

“3 Kings” doesn’t attempt to be anything more than a session of stunting. And why should it? How often do three larger-than-life lyricists get together to take a victory lap? “You should listen to this beat through my headphones,” rapped Dr. Dre, a brag that few rappers will ever be able to repeat. Ross flipped the line, saying, “We should listen to this track in my Maybach.” Then you have Jay, who goes, “Play this shit while you play around with my crown.” All three are brimming with triumphant energy as they swap achievements and wax poetics over pristine Jake One production. It was a moment then, when the track first appeared in 2012 on God Forgives, I Don’t, and it even feels like a moment now. — Y.P.

20. “Maybach Music V” Feat. Dej Loaf

There’s no such thing as “over the top” when you’ve been a boss for a complete decade. For Rather You Than Me in 2017, Ross had the supreme confidence that comes from knowing that his spot was cemented, his legacy as Teflon as the mafiosos he’d modeled his public persona after. So, why not do something truly unexpected? For the fifth “Maybach Music,” Ross cedes over two minutes — crucially, the first two — to highlight a voice he loved that might not have been getting as much love as he believed it should (I tend to agree; Dej Loaf’s last two independently released projects were criminally overlooked). — A.W.

19. “Rich Is Gangsta”

In the 1988 Blaxploitation spoof I’m Gonna Git You Sucka, Harlem hero John Slade explains the group of musicians standing behind him is there to provide his “theme music.” As he puts it, “every good hero should have some.” “Rich Is Gangsta” is what that band would play if that film came out today. Continuing the Rick Ross tradition of exultant horns, exuberant drums, and chant-like soul samples, the Black Metaphor and Diddy-provided beat backdrops another ferocious declaration of his mission statement. Dropping as it did after his correctional officer kerfuffle, it also gave him a chance to explain his side of the story: The streets got cold, so he got a job. Hey, it all worked out in the end. After all, the heroes always win. — A.W.

18. “The Devil Is A Lie” Feat. Jay-Z

By this point, you’ve probably figured out that it’s no coincidence that I claimed the bulk of the Rick Ross songs with Jay-Z features on them for this list. Can you blame me? Something about working with Rick Ross — a fellow former hustler with an undying, almost compulsive love for the craft of rap — brings the best out of Jay. The bluesy beat gives both rappers a plush playground in which to get their kicks, yes. But also: some of my favorite verses are the ones where Jay one, blasphemes, and two, delves as deep into his “watch my wordplay” bag as he can possibly get. Here? Check and check. — A.W.

17. “Outlawz” Feat. 21 Savage, Jazmine Sullivan

One would expect Rick Ross and 21 Savage to be frequent collaborators. Both run in close proximity to Drake, they have an affinity for financial literacy, and their ears are both drawn to soul beats and trap sounds, yet, for reasons unknown to me, the AraabMUZIK-produced “Outlawz” is their sole crossover effort. The swelling, soulful score constructs a suitable meeting ground for two straight shooters with gospel truth to get off their chest alongside Jazmine Sullivan, who sings to the heavens on the hook. As a strong record, where all three co-stars performed worthy of their stature, “Outlawz” achieved what was necessary with a lineup that may never happen again, so cherish it. — Y.P.

16. “Little Havana” Feat. Willie Falcon, The-Dream

The first flex is the Willie Falcon intro, a helluva way to open a record called “Little Havana.” The second flex, if it’s worth considering a flex, is how Ross was on his 11th album in his 15th year rapping with the veritas of a reflective veteran, yet, he doesn’t seem worn or burnt out, but rather revived and resolute. “Problem was I never was a prodigy,” begins the first verse, starting honestly, before name-dropping Roger Goodell, Meek Mill, Omarion, and L.A. Reid throughout his stream of consciousness. Although short, “Little Havana” is potent. Like hearing an entry from an audio journal recorded while overlooking the Miami skyline on a day when the MMG boss had a lot on his mind with no one to speak with. This brand of isolative recollection often makes for good rap music, especially when done right. — Y.P.

15. “Diced Pineapples” Feat. Drake, Wale

As great as Ross is at booming, boastful luxury rap, it’s impossible to overlook how similarly skilled he is at sex raps — indeed, he’s probably one of the only male rappers who actually seems kind of good at them. Maybe it’s the Barry White-esque vocals, perhaps it’s the fact that he litters his come-ons with stuff that women might actually want to hear (“baby girl, I just want to see you well off”) rather than juvenile locker room talk, but it’s undeniable. That he pairs these sweet nothings with two of rap’s other finest smooth talkers in Drake and Wale makes this single from 2012’s God Forgives, I Don’t the perfect date-night playlist inclusion. — A.W.

14. “Maybach Music VI” Feat. John Legend, Lil Wayne

By the 2019 release of “Maybach Music VI,” the Maybach Music series had spent over a decade upholding a standard for luxurious compositions and high-life lyricism. Much like its predecessors, the sixth installment added a fresh page to the magical portfolio of J.U.S.T.I.C.E. League-produced symphonies. Rick Ross, John Legend, and Lil Wayne all have inspired vocal performances that complement the exquisite live instrumentation quilted together like audible fabric woven from the finest silk. By now, we all know you don’t listen to a Maybach Music record just for bars, but also the beat, and “Maybach Music VI” sonically delivers magic carpet music for street rats with genies who would use one of their three wishes on a 2021 Mercedes S-Class. Or, as John sings on the hook, “It feels like we’re floatin’ up in outer space.” — Y.P.

13. “Big Tyme” Feat. Swizz Beatz

There is an underrated quality to rap songs where guest features only do the ad-libbing. Jeezy’s background vocals on Kanye’s “Can’t Tell Me Nothing” is a top example, but Swizz Beatz’s animated ad-libs on “Big Tyme” deserves an honorable mention. His lively cadence enhances the conviction-filled verses that course over the rollicking Just Blaze beat to create a record that sends a double dose of adrenaline to the eardrums. Not many songs on this list can be considered underrated, but “Big Tyme,” as a cut found on the 2019 Port of Miami 2, hasn’t had the chance to age like other classics. Give it time though, history will honor this boisterous banger. — Y.P.

12. Rich N**** Lifestyle” Feat. Nipsey Hussle, Teyana Taylor

Port of Miami 2, the tenth studio album by Rick Ross, was released on August 19th, 2019, five months after the tragic passing of late Crenshaw rapper Nipsey Hussle. Nipsey appears on track eight, “Rich N**** Lifestyle,” with a verse that references everything from Tekashi 6ix9ine snitching, hip-hop’s dominating presence on the Billboard charts, and his courtside appearance in a viral Lakers video. And although the Cardiak-produced, Teyana Taylor-featured record is more than Nip, his presence alone gives the song a stamp of timelessness. He was so alive, so aware, so gifted, and to know this song holds one of his last observations in rhyme, it’s just a bit more special than if it didn’t. — Y.P.

11. “Hold Me Back”

Rick Ross primarily operates in two modes: Either laid-back in an opulently-appointed lounge, puffing a Cuban cigar with a three-digit glass of whiskey in hand, or marching through the streets of Carol City, with a three-week beard, wild-eyed, and waving a pistol. This one fits firmly into the latter mode, with a clamorous, gothic trap beat announcing his coming like that ominous whistle that presaged Omar strolling through the Terrace projects with that shotgun over his shoulder. Ross, four years into his career proper at this point, still sounds voracious, like he hasn’t even seen an edible meal in weeks, much less the decadent treats he’d undoubtedly become accustomed to by then. His ability to do so is what’s kept him at the top of his game ever since. — A.W.

10. “Free Mason” Feat. Jay-Z

Some of y’all might be too young to remember this, but there was a time on the internet, before QAnon and junk vaccine science, when all the conspiracy theories revolved around a handful of Black recording artists, for some reason. And nearly incalculable inches have been written about the whys and hows, and yes, it was just as exhausting as it sounds here. But it was all worth it, if only because it sparked Jay-Z and Rick Ross to cook up this gem, which is half a cheeky response to the nonsense that frankly didn’t warrant it and the other half a pure lyrical exercise that finds Jay splaying out his lanky limbs in a churchy, epic-sounding production by The Inkredibles and establishing just how badly the game needs him around. — A.W.

9. “Tears Of Joy” Feat. CeeLo

As much as it pains me to co-sign a song that misrepresents the words of Bobby Seale and the philosophy of the Black Panthers, conflating them with Ross’s hedonistic abandon, here’s the thing: “Tears Of Joy” is quite simply one of the best-produced, best-written, most compelling works in Ross’s extensive catalog. There’s an authentic pleading behind CeeLo’s voice on the hook and No I.D.’s beat, replete with gently weeping guitars and driving pianos straight outta the pulpit, the tension between the divine and profane is palpable. A revolutionary he isn’t, but we’ll forgive Ross a little sacrilege for relating to the struggle. — A.W.

8. “Maybach Music III” Feat. Erykah Badu, Jadakiss, T.I.

They say “bigger is better” and it’s obvious Rick Ross subscribes to this viewpoint, as each successive installment in the “Maybach Music” series seems to get (it’s necessary to keep these observations in the present tense at this point) more elaborate, more grandiose, with higher profile features and heightened crescendos. By the time Teflon Don came out in 2010, fans thought they knew what to expect, so the obvious solution was to bring in a full orchestra, complete with some big-band drumming and an operatic mid-point breakdown, and one of the signature soul singers of the past decade to smooth out the chorus as the guest verses — courtesy of prime Jadakiss and T.I. — got more rugged. — A.W.

7. “Idols Become Rivals”

“Idols Become Rivals” was not a record anyone saw coming. Not if you followed the career of Rick Ross and understood his admiration for Birdman and Cash Money Records. But Ross is a rapper of honor; a businessman of ethics and Birdman’s history of unethical behavior finally reached a point where he could no longer turn a blind eye. The disgust, the disappointment, the disapproval, all that went unsaid from years of silent acceptance comes out in a scathing yet poetic assessment of a friend turned foe. “Idols Become Rivals” is masterful as an artful attack and a hall-of-fame-worthy exhibition of killing your heroes with critique, not kindness. — Y.P.

6. “Santorini Greece”

“Santorini Greece” samples Judy Bailey Quartet’s “Colours Of My Dreams,” a mesmerizing source made even more majestic by Bink! and his ingenious rearrangement of each note, riff, and melody to build an exquisite beat layered in lush tones, touched by jazzy textures. The music brings a brand of extravagance synonymous with private islands, foreign cars, and expensive taste. A perfect canvas for picturesque verses delivered with laid-back assertion. Although boastful, “Santorini Greece” is where wealth-talking braggadocio meets race-related introspection from a Black American in a manner only possible for late-career Rick Ross, the poet laureate of hood billionaires. — Y.P.

5. “Maybach Music IV” Feat. Ne-Yo

As the only Maybach Music not to feature any guest verses from star-studded associates, “Maybach Music IV” may not look like a summertime blockbuster in the liner notes, but give the sun-kissed track a listen. You will find another gorgeous J.U.S.T.I.C.E. League-produced work of art. Musically, the satisfying instrumental does not stop progressing, an ever-moving composition that conveys a rich and soulful sound deserving of the fan-favorite series. The aid of Ne-Yo in the latter half makes “Maybach Music IV” feels like an evolved, more mature version of their 2010 collaboration, “Super High.” Giving the piece a sense of artistic refinement, a show of growth. — Y.P.

4. “Hustlin’”

Repeating “22” seven times in the third verse of “Hustlin’” did not earn Ross any prestige as an exceptional emcee, but his 2006 debut single wasn’t to prove technical prowess, instead, the Street Runner-produced anthem promoted a far more significant fact: Repetition invokes remembrance. With its repetitious hook, a savvy soundbed, and simple summer-time lyrics, “Hustlin’” successfully stuck to eardrums. Creating a lane for a newcomer barely known outside of Miami. As the street record that introduced his voice, name, and style to an unsuspecting industry, “Hustlin’” advanced the young Rozay to higher heights without having to use those favors owed to him by Noreiga. Classic. — Y.P.

3. “Aston Martin Music” Feat. Drake, Chrisette Michelle

“Aston Martin Music” is a song that could not fail. Every element feels carefully curated to win over listeners, young and old. The LL Cool J interpolation, Drake and Chrisette Michelle sharing half the chorus, and J.U.S.T.I.C.E. League’s balmy 90’s R&B-inspired beat found an intersection between simple and sexy, new and nostalgic that ultimately gave Ross a 3x platinum hit with over 330 million views on YouTube. To hear it today, more than a decade later, the magic hasn’t worn off. For those who came of age in the 2010s, the track will return you to memories of when 106 & Park still existed, when radio still broke records. A different time, a different era. — Y.P.

2. “B.M.F. (Blowin’ Money Fast)”

The sound: colossal. The verses: colossal. The attitude, the energy, everything about “B.M.F. (Blowin’ Money Fast)” towered over the trap soundscape in 2010 with an anatomy bigger, more gigantic than its sizeable contemporaries. The Lux Luther-produced atom bomb not only separated the giants from the gladiators but further proved that the Dade County boss wasn’t just building a catalog for stadiums, he could make massive records fit for Roman Colosseums, fit for Caesars Palace. Thirteen years later, the music still communicates a keen sense of glorious demolition, invigorating destruction, and a feeling best described as an intoxicating upheaval over enemies and opposition. — Y.P.

1. “Maybach Music” Feat. Jay-Z

You never get a second chance to make a first impression. Fortunately for Rick Ross, when he kicked off the signature series of anthems named after his record label (before it ever was a series), he knocked it out of the park. Coming off the platinum debut Port Of Miami, Ross faced the dreaded sophomore slump and the challenge of topping the fan-favorite “Hustlin’.” He more than accomplished that with the No. 1-selling Trilla, which spawned another top-40 hit in “The Boss”; however, the true achievement was “Maybach Music,” which established the luxury mafioso rap sound that would come to define much of his latter-career output and give him the perfect, elegant image overhaul that ensured his longevity throughout the 2000s and ’10s. That Jay-Z raps one of own his best late-career verses here, re-establishing himself after his own critical stumbles in 2006’s Kingdom Come, is just icing on the cake. — A.W.