Lyrical Lemonade’s Cole Bennett Documented a Moment in Hip-Hop. Now He's Creating a New One

Joe Rocha / Courtesy of Def Jam

This story was featured in The Must Read, a newsletter in which our editors recommend one can’t-miss GQ story every weekday. Sign up here to get it in your inbox.

In the opening credit sequence of Into the Wild, Sean Penn’s 2007 adaptation of the John Krakauer book about a young man who gives up all his possessions to live in the Alaskan wilderness, that young man—played by Emile Hirsch, wide-eyed and half-prepared—treks up the snowy mountain where he’ll hunt, scavenge, brace against the elements, and eventually die. While he climbs, a simmering Eddie Vedder song swells: “I've got this light,” Vedder growls, “and the will to show/I will always be better than before.”

A little over a year ago, Cole Bennett, the 27-year-old music video director, sat down to watch this scene and was struck by inspiration. “It feels like this big feat, this big moment,” he says, lounging on the patio of Soho House in West Hollywood. This is a few days before the release of All Is Yellow, a compilation album credited to Lyrical Lemonade, the music blog Bennett founded in high school, which has since unfurled into a multimedia and live promotion company. Bennett and a pair of friends are inconspicuous among the wealthy, well-dressed crowd, save for the black hats with “ALBUM” emblazoned across the fronts in bright white letters.

The Vedder/Hirsch ascent, Bennett goes on, was more than a metaphor: it was an emotional and sonic blueprint for the way he wanted the Lyrical Lemonade album to begin. “I need Sheck Wes shouting shit!” he remembers thinking. But also: “I need it to feel beautiful! Then there needs to be a buildup—and then the beat needs to drop a minute into the song, and we need Ski Mask [the Slump God] to come in and come crazy! And then there needs to be a wild bridge. Then I need J.I.D. on it!” What Bennett is describing is exactly what came to pass on “Fly Away,” All Is Yellow’s grandiose opening song. The latest in a string of records patterned on the slow-building dynamics of Meek Mill’s now-classic “Dreams and Nightmares,” it’s staked on tension and release: ornate until it’s animal, considered and then instinctive.

“All these ideas came together so purely,” Bennett says of the rappers and structural tics he knew he wanted to comprise “Fly Away.” While this may be true, the process of putting together All Is Yellow was endlessly complex and required him to call in some favors and trade others, leverage Def Jam’s money and infrastructural know-how and, presumably, coordinate a collection of iCal pages as complex as the Dead Sea Scrolls. All told, 34 rappers and singers appear on the LP, with nearly as many producers contributing work behind the boards. It’s a compilation album that Bennett was determined would defy the popular image of one—that of spare parts slapped together, obligation the only discernible throughline.

In discussing the record, Bennett is remarkably evenhanded. He is, of course, in salesman mode; custom hats aside, this is someone who parlayed a music obsession and a digital camera into a central role in one of the definitive hip-hop movements of the 2010s, to say nothing of the reach and profitability that Lyrical Lemonade and his live events have garnered, all without rapping or producing himself. But he also confesses that, in trying to wrap what he refers to as the “visual album”—videos for half of the 14 tracks have been released, with the other seven coming—he let linger some transitional hiccups that he now believes could have been ironed out, and he’s not wholly satisfied with the final sequencing.

There is also a palpable exhaustion. In addition to the recording and post-production of All Is Yellow, Bennett has been flying around the country to finish those videos, dressing artists in black suits and yellow ties and shooting them in front of a bright yellow curtain in whichever city has allowed for a tiny gap in their schedule. “I needed to be the one who was absolutely flexible,” Bennett says of his plan for the process.

But this piecemeal approach has provided him yet more room to tinker—as in the video for “Say Ya Grace,” which features the artists who recorded the song, Chief Keef and Lil Yachty, but also Big Sean, G Herbo, and Denzel Curry. Not only do those three appear on screen, but their ad-libs from other All Is Yellow session files have been ported into the version of the song that will accompany the clip. When Bennett explains his motivations for pulling notable rappers without obvious connections to the headliners onto his set, he gets at the unique blend of raw enthusiasm and marketing-speak that has seemed to animate his career from its beginnings. “The idea of unity, and people coming together, is the shit I’d want to see as a kid,” he says, before catching himself. “Not even as a kid—as a man, as a consumer.” The emphasis is mine, but it’s also his.

And yet that commercial sensibility seems to be a lens Bennett can see the world through when he chooses to, rather than one that blinds him to what drew him to the genre in the first place. If nothing else, All Is Yellow is a fascinating snapshot of the way rap evolved over the course of the 2010s: the way the label system cratered, then rebuilt itself and reasserted control; the way subgenres and regional scenes splintered smaller and smaller until they were subsumed back into the mainstream. Bennett was there to document all of it—at least nominally. As he says, sometimes those involved in creative movements are too close, too caught up to see when their footing is becoming unsteady. Put another way: “Nobody realized what was happening.”

Bennett was born in Plano, Illinois, a quiet town of about 11,000 people 55 miles west of Chicago, in May of 1996, just over a month before Do or Die and Twista’s “Po Pimp” became a regional sensation. By the time he was in high school, that nimble, Bone Thugs-indebted school of Midwestern rap had been blotted out by drill music. That thunderous genre married the finesse and complexity of Chicago’s dance music rhythm to gothic beats and bellowed verses and ad-libs, mostly delivered by teenagers who had figured out how to distill the emotionally fraught experience of living in violent neighborhoods into quick, epigrammatic bursts.

When sales of physical CDs cratered in the late 2000s, so did the budgets major labels earmarked for rap albums and their promotional cycles. By the time Bennett was expanding beyond blog posts and concert reviews and into actual music videos, the epic scale of videos by Hype Williams et al. had shrunk down to practically nothing. Early drill videos were ingenious for the way their tight framing and kinetic camerawork drew out the micromovements within drill songs that critics too often described as bludgeoning and two-dimensional. But the directors had few other options.

The wave of hip-hop with which Bennett is most closely identified is not drill, but the so-called “Soundcloud rap” that emerged in the mid-2010s. As with many subgenres, the name is sometimes wielded pejoratively; no one can agree on a precise definition of its boundaries or chronology, and some artists considered key figures in the movement chafe at the association. One way to understand it is to imagine a whole generation of young artists born from Lil Uzi Vert’s rib: rappers comfortable rapping through serrated distortion or contorting their voices into earnest, urgent melodies. They were fluent in not only the pop-rap of their childhoods but the pop-punk as well; lots of the work had menace, but almost all of it could soundtrack a montage of rebellious teens running through a mall.

These inherent contradictions—between stoicism and emo-indebted songwriting, regional specificity and the haze of internet culture—were actually better explored visually by constrained productions, rather than in videos shot on rented yachts or from helicopters. In the Bennett-directed video for “D Rose,” a breakout hit by Miami Soundcloud star Lil Pump, the then-teenaged Miami native is depicted shirtless or in BAPE hoodies, wearing a designer backpack (itself a provocation about stylistic orthodoxy in rap) swaying or shaking his hair in small, concentric circles. Rather than pan to extras he can’t wrangle or cut to a club scene he can’t afford to stage, Bennett overlays simple but nervy animated elements, which make Pump seem to vibrate—because, of course, he does.

But the money wasn’t far behind. “I remember doing a Rolling Stone interview in 2017 and being like, ‘Hold on, I think this is bigger than we realized,’” Bennett says. By that point he was well on his way to becoming the primary documenter of the movement, having also directed (or would be soon to direct) videos from Ski Mask the Slump God, Lil Xan, and countless other architects of the style. “There were these Soundcloud artists who were doing bigger numbers than mainstream acts at the time who all started to get signed,” he says. “And then everybody got signed. The labels definitely caught on late to what was going on, and then—I think out of panic—they just signed everyone.”

Today the “D Rose” video has more than 200 million views. But Pump’s career is also a sort of parable about alternative cultures being ground up into pulp by corporations. Warner Bros. signed him and nudged him toward beats that mortgaged the minimalism and specificity of his early work for something that could conceivably—texturally, even—exist on radio playlists beside Rick Ross and Drake. The returns diminished quickly, to the point where, in 2023, his self-released Lil Pump 2 failed to chart. This was a year and change after the IRS filed a $1.6 million lien on his home. At the time of this writing, Lil Pump is 23 years old.

But Bennett survived the mutation of Soundcloud rap, aligning himself with then-budding Chicagoan superstar Juice Wrld, identifying other regional breakout candidates like Memphis’s NLE Choppa and L.A.’s Blueface, and tapping into a network of A-listers, including Wiz Khalifa, Post Malone, Eminem, and even Blink-182. Yet he’s still wistful when he talks about the days when a cadre of young artists, headquartered in South Florida, were still, in the parlance of the times, pre-revenue. “When I think of the Soundcloud wave, I think of it before any of the artists were signed,” he says, “when people were really sleeping on peoples’ floors. There was really a community—it was like high school. It was really strange, man. There was so much overlap that people don’t even know about, stories people will never hear.”

It would stand to reason, then, that Bennett would have a complicated relationship with the major label system. As he tells it, his attitude toward working with giant companies has wavered over the course of his career. “I think in 2010 it would have been the coolest thing ever,” he says of the deal with Def Jam that he brokered for All Is Yellow. “Now, in 2017, if you told me that, I probably would’ve been against it. I went through a period of my career where I was very anti-label, anti-industry, anti-all these things. [But] as time went on, as much as that’s always going to be a part of me, I started understanding the idea of infrastructure and not being able to do everything myself. I need to find a way to be able to afford to shoot 14 videos and put this together and people who are patient with me, and people who understand the business in ways I might not. This was barely possible as is; I couldn’t have imagined doing it with just me and three or four of my friends.”

Bennett offers, unprompted, one of the most common quips rap fans made about the album when it was announced: that it should have dropped in 2017 or ‘18. He doesn’t seem angered by the idea; he simply argues that he wouldn’t have had the necessary perspective at that point in his life and career to make an album that would satisfy him. What he doesn’t say is that, in 2024, the Lyrical Lemonade album serves as something like a time capsule. Juice Wrld appears posthumously; Ski Mask and G Herbo offer competing visions of the way early- and mid-2010s stars could develop into steady handed veterans. Lil Yachty, Joey Bada$$, and even Corbin—known initially as Spooky Black—similarly exist in a kind of permanent, digital halflife, their continued evolution seeming to rebuke skepticism about one-time online sensations. And of course, the very existence of a Def Jam-issued Lyrical Lemonade album could dupe someone into believing rap’s blog era never ended at all.

While Bennett is a credited producer on nine of All Is Yellow’s 14 songs, his account of the sessions casts him in more of a traditional producer’s role: directing traffic in the studio, keeping one eye on granular details and the other on the macro vision. Yet as with any curatorial project, a touch of the personal bleeds through. When he describes the session that eventually yielded the song “First Night,” it sounds like a hastily filled-in Mad Libs page, or an A&R’s fever dream: Teezo Touchdown, Cochise, Lil B, Denzel Curry, Juicy J, a flip of Three 6 Mafia’s raucous “Ass & Titties” bookended by the type of contemplative piano you’d find in one of those somber pop song covers that soundtrack every new movie trailer. A recipe, it would seem, for an uncanny sort of streaming-bait.

But enlisting the Memphis legend had a special significance. “One of my best friends growing up took his life at the end of 2022,” Bennett says. “His favorite rapper was Juicy J. I had a built a relationship with Juicy over the last few years—nothing crazy, but we talked here and there. We had each other's phone numbers. So the first thing I did was reach out to him and say, ‘I need you as a part of this album—you were my boy’s favorite rapper.’” At the end of “First Night,” when the beat drops away for a second, Juicy invokes Bennett’s friend: “Rest in peace, Miggy 2 Times.”

“If he heard that…” Bennett’s voice trails off. “The goal is for him to hear that. The goal is to do things that maybe no one else understands besides me and a couple of my friends I grew up with—but it means so much to us.”

That desire for real investment led to a number of false starts in the creation of All Is Yellow. When Bennett first set out to put together the LP, he did what he derisively says is “what you would expect from a music video director making an album”—canvassing producers for beat packs and shooting files off to rappers, hoping they’d email back some interesting vocals. Bennett got some demos back; he was deflated. Eventually, though, he and a producer sat down and retrofitted a new beat to a rapper’s verse. It not only ensured there was more time and attention paid to the song, but unlocked a key connection in his brain: “I was like, ‘Oh, wow, we can really build concepts from scratch—this feels like video editing. This feels like what I already do.’”

And so he started having artists rap on production with no drums, including Lil Durk’s sweeping performance on early single “Guitar In My Room,” a song around which the otherwise disparate pieces of All Is Yellow seem to orbit. “His cadence switches and all these things were just his natural energy going up and down,” Bennett recalls of that session. “We built the track around that.”

Making music in this way takes all the aforementioned financial and logistical acrobatics—but it also takes time. When I ask Bennett how the visual album component changed him as a director, he answers quickly, tying his long-gestating skills in that arena to the new musical role: “Patience.” Marshaling people for his own venture, he explains, is fundamentally different from working for hire on other peoples’ videos. When Lyrical Lemonade is the credited headliner, he explains, “I have to get the artist excited. Usually, if an artist is late—it’s their video. If they’re not excited or not fully involved they'll have people on their team pushing them to be ready. But on this project it was on me to get everyone excited, to keep everyone there long enough, to get every ounce out of people that I can get.”

Bennett is today something of a star himself: last year he was briefly the subject of tabloid headlines declaring that he and a given supermodel were “‘Moving in a Romantic Direction’ (Exclusive).” He hopes to parlay his video directing career into feature films; he says he sees his future output as a blend between the work of Steven Spielberg, Tim Burton, and Harmony Korine. “I want to have fun,” he says. “I’m not chasing some big blockbuster career. I look up to Harmony in the sense that he storytells in a very unique way, and he kind of has this ‘I don’t give a fuck’ mentality: ‘This is what I’m making, this is what matters to me.’ Sometimes there’s not even a clear story you’re following—it’s just vignettes that evoke emotion. And that’s my form of storytelling, what I relate to: things that are open to interpretation.”

Which is how someone might take the image of a young man climbing up a mountain, slightly deluded and destined to die alone in the elements, as a triumphant one. What Bennett’s undertaken with All Is Yellow is not exactly quixotic (major labels are going to issue records they believe will be profitable) and it is not exactly redistributive (the contributing artists are almost uniformly established stars). But the expensive Def Jam release that gestates for more than a year and is scrutinized down to the smallest detail is at least a little evocative of an era before streaming turned release schedules to cycles of constant churn. What Bennett is chasing instead is something permanent, something durable. “You see that yellow curtain,” he says of the backdrop ever present in All Is Yellow’s videos, and “you know exactly what it means.”

Originally Appeared on GQ

More Great Stories from GQ