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Chicago-based visionary Cole Bennett started out shooting for up-and-coming teens and twenty-something blog favorites, but in the past five years, he has become one of rap’s foremost music video directors, working with top names like Eminem, J. Cole, Lil Durk, and more. He’s even shot for actor Jack Black, delivering a colorful video for Black’s Super Mario Bros. Movie crowd-pleaser, “Peaches.”

“I was a very visual person, but I never knew that I loved music videos,” Bennett said in a 2021 XXL interview. “I always had this idea since I was super young of what it would look like if I made a music video.” For nearly a decade, Bennett has been bringing these ideas to life to the praise of the artists he works with and his growing fan base.

With that being said, we decided to scour Bennett’s Lyrical Lemonade page for his best work. Here are the 10 best Cole Bennett-directed music videos.

Honorable Mention: JID & J. Cole — “Off Deez”

Okay, it’s a pretty basic concept with workmanlike execution, but it might be the best song Bennett’s ever done a video for. JID and J. Cole are left turns for Cole Bennett, if you take in the entirety of his filmography, so it was pretty meaningful that the Dreamville cohorts teamed up with him on this standout from JID’s DiCaprio 2. It’d be nice to see them do it again.

10. Ski Mask The Slump God — “Catch Me Outside”

An early standout from both Bennett and Ski Mask The Slump God, “Catch Me Outside” perfectly illustrates the possibilities of a limited budget when you’ve got unlimited imagination. Awash with eye-popping visual effects, “Catch Me Outside” offers a prime example of Cole’s early style; it’s raw, but flashes of his future brilliance shine throughout. Many of the techniques Bennett used here eventually became hallmarks of his style, and with polish, set off the concepts of his future videos with Cordae and Eminem.

9. Central Cee — “Doja”

As “Doja” is one of Bennett’s more recent videos, its simplicity might seem out of place in a list featuring so many brain-bending, colorful visuals. But it also marks Bennett’s transition from colorful collaborator to kingmaker; Central Cee is a star stateside after working with Bennett, making the most of essentially an indie budget to secure the coveted director’s services and show he belongs on the biggest stage.

8. Jack Harlow — “What’s Poppin”

While the visuals are pretty tame for a Cole Bennett production, Harlow’s “What’s Poppin” video is still representative of the elements that have made Bennett’s videos so eye-catching and amusing. Even the low-key imagery mirrors Jack’s tongue-in-cheek humor, highlighting and elevating it with some juxtaposed elements as bottle service and satin sheets at a late-night diner and a woman “smoking” a french fry like a cigarette. It’s also impossible to discount what the video did for Harlow’s career, taking him from an indie unknown to a potential chart-topper with 170 million views.

7. Drake — “Another Late Night” Feat. Lil Yachty

Say what you want about Drake, but “Another Late Night,” at least visually, has been the height of his last couple of rough years. Drake and Yachty have great chemistry, and despite the relatively straightforward treatment, the video manages to be eye-catching and stand out from the rest of Drake’s admittedly wonky catalog.

6. Lil Durk — “Kanye Krazy”

Bennett’s referential style comes to a head in Durk’s “Kanye Krazy” video. Pulling from infamous clips from the titular auteur’s oeuvre and public outbursts, Durk reimagines the videos for “Runaway,” “Bound 2,” and “I Love It” — specifically, the moments in which Kanye’s mental illness seems to have gotten the better of him, for better or worse. This was just after Drake’s “Laugh Now Cry Later” had put Durk back on the national map, so to speak, so the cheeky visuals helped aid in lending mainstream audiences a better sense of Durk’s personality outside his harrowing drill stories.

5. BabyTron — “100 Bars”

BabyTron, like Central Cee’s “Doja,” is a more recent addition to Bennett’s filmography, albeit one with a much higher concept. It’s executed deliriously well, with a new BabyTron outfit/persona for each of the titular “100 Bars” and seamless transitions between each. It’s a format that Bennett would return to with Eminem’s “Tobey,” but it’s impressive that the Detroit and Chicago natives were able to make this work without the benefit of a huge star (and the accompanying budget). BabyTron, for all the lethargy of his flow on the song, also appears to be having a ball, as does comedian Andy Milonakis in his cameo role.

4. Eminem — “Godzilla”

“Godzilla” is the moment Cole Bennett “made it,” in the sense that he began working with established megastars like Eminem in addition to the SoundCloud standouts in his own DIY cohort. Fittingly, the increased budget came along with some stunning visual effects to spice up the flow of the video’s narrative while enhancing Bennett’s trademark surrealism. Em gets punched in the face by Mike Tyson, breathes fire, vomits Legos, and performs surgery alongside longtime collaborator Dr. Dre. And speaking of collaborators, “Godzilla” is a hallmark moment for Marshall too; it’s the first time he really embraced the SoundCloud rappers he’d formerly spent huge segments of his albums belittling.

3. Polo G — “My All”

Of all Cole Bennett’s most frequent collaborators, he most frequently turns in his best work with hometown artists like Juice WRLD and Polo G. In the video for “My All,” the Chi-Town natives tone down the usual comedic elements of Cole’s catalog in favor of something more emotionally resonant. It looks simple, but it’s not; a seated Polo performs the lyrics as a montage of memories both celebratory and traumatic, scroll behind him. The fourth wall break at the end is a fun surprise.

2. Cordae & Juice WRLD — “Doomsday”

My personal favorite out of the videos presented here, “Doomsday” takes a simple concept and adds stupendous visual flair with the aid of facial overlay technology. This is how you pay homage to departed artists; Cordae puts on a clinic as both himself and his late friend Juice WRLD, while Cole puts deepfake algos to an actual artistic use that doesn’t require stealing the work of real artists.

1. Juice WRLD — “Lucid Dreams”

The video that put Bennett on my personal radar, “Lucid Dreams” is far from his most stunning. But it’s hard to argue with a billion views; “Lucid Dreams” is the song that made Juice a star, it’s still his biggest song to date, and the video displays Cole’s gift for dreamlike visuals, which also fits the theme of the song.