Most people hope for a moment that changes their life. Even better if it impacts the culture around them.
By the summer of 2016, Cole Bennett had at least three such moments.
Barely out of his teens, the burgeoning director had garnered 1 million views with his music video for Chicago rapper Famous Dex. He booked Philadelphia rapper Lil Uzi Vert’s first Chicago show, which sold out Metro in Wrigleyville. And he co-founded the Lyrical Lemonade Summer Bash, a precursor to Summer Smash — the premier hip-hop festival of the Midwest, which kicks off Friday at Bridgeview’s SeatGeek Stadium.
Through it all, he remembers thinking, “I want to have this much fun forever.”
Ten years, 500 music videos, eight festivals and one multimedia empire later, the thrill hasn’t faded. This week at his Lyrical Lemonade headquarters in Chicago, Bennett raved about the lineup for Summer Smash 2026, his company’s festival that this year features headliners Playboi Carti, Lil Uzi Vert, Chief Keef, Baby Keem and Skrillex.
He also gushed about his newfound passion for shooting or transferring music videos onto tactile film. (The results can be seen in visuals for Justin Bieber’s “Yukon,” Sienna Spiro’s “Die On This Hill” and more.)
The now-30-year-old entrepreneur is also venturing into full-length filmmaking with a documentary on Chicago rapper Chief Keef and a narrative movie that he is still writing. He appears to be maturing, aiming to elevate his artistry by reducing visual effects in favor of more “practical world-building.”
But whether it’s digging into the juggalo subculture for a microdocumentary or highlighting animatronics in a Clipse video and forthcoming film, Bennett hasn’t lost his sense of whimsy and wonder.
“I always worried that, when I got older, my excitement, my passion and my imagination would wither,” said Bennett, who splits his time between Chicago and New York. “But I feel like it’s more intact than ever, and that makes me really excited for the future.”
Finding kindred spirits in Chief Keef, Juice Wrld
Bennett also gravitates toward others, like Chief Keef, who share his endless curiosity. The Chicago-born drill rapper’s enthusiasm for learning is on display in Bennett’s documentary, which is still in production. Bennett said he was struck by a visit to the rapper’s home in Los Angeles.
“You’re expecting his garage to be filled with all these cars that he has and posts online, but there are screen printers, direct-to-garment printers and 3D printers,” Bennett said. “He’s an artist and he has all these things that he truly nerds out about. It’s really beautiful to see. He inspires me.”
It’s a side not often seen, as Keef’s reputation was marred by legal troubles that eventually prevented him from performing in Chicago for 10 years. In 2024, he returned to the city in a historic set at Summer Smash.
Bennett said he doesn’t have a timeline for releasing the film, which is being produced by Kenya Barris‘ Khalabo Ink Society. He is determined to get Keef’s story right.
“He’s one of the greatest artists of our generation,” Bennett said.
He found a similar enthusiasm for art in Chicago rapper Juice Wrld, who died of an accidental overdose in 2019 at just 21 years old. Bennett directed multiple videos for the artist, including the visual for the hit “Lucid Dreams,” which currently has 1.1 billion views on YouTube.
He admired Juice Wrld’s appreciation for other artists at all levels of success.
“There wasn’t anyone he didn’t want to work with,” Bennett said. “If he met someone and he liked them as a person, he’d make a song with them.”
Whether he was performing for 100 people or 40,000, Juice Wrld, born Jarad Anthony Higgins, was always excited, Bennett said.
“We’re so blessed and privileged to be in a position where we can do what we love for a living,” he said. “He never took that for granted.”
From Plano pupil to Windy City wunderkind
Bennett has worked with other notable Chicago artists, including Ye, Lil Durk, Vic Mensa, G Herbo, King Louie, and siblings Chance the Rapper and Taylor Bennett. He was instrumental in exposing many of them to new audiences through directing their music videos, capturing performance footage or booking them for shows.
“He was a man of the people,” said Taylor Bennett (no relation). “He had brought all of these groups together in one room, and all of these people felt like they were comfortable or at home, because this was Cole’s space.”
The rapper and record label owner also praised Bennett for consistently supporting new artists.
“He has never been about chasing who is already established,” Taylor Bennett said. “He’s never stopped working with Chicago’s young, new talent.”
Cole Bennett’s childhood friend Elijah Wallace agreed.
“You can’t really talk about Chicago music without talking about Cole and Lyrical Lemonade,” said Wallace, an artist who also collaborated with Bennett in the early days of his career. “They go hand in hand.”
But before he impacted the scene, he was a hip-hop obsessed kid growing up in Plano, Ill. He read music websites, downloaded mixtapes and printed out photos of artists, which got him in trouble with his mother one day.
“I wasted all the ink because I printed out every Lil Wayne picture I could find and made a shrine in my bedroom,” he said. “She was so mad.”
But his mother became his biggest cheerleader, even helping him coin the name Lyrical Lemonade, which he originally founded as a hip-hop blog in 2013.
“I would just write articles on music I was into, hoping that I could show someone their new favorite artist,” he said.
Bennett also began filming music videos featuring Wallace and other friends, who formed a rap collective. Visuals for their songs “Tuna” and the “Tuna” remix featured shots of people doing cannonballs in a pool and Wallace spraying whipped cream on the emblem of a luxury car.
“I’m not surprised at Cole’s success, because he’s always been one of the most charismatic and popular people that I’ve known,” Wallace said. “He can become friends with anyone.”
Bennett eventually expanded his clientele, relocated to Chicago and studied at DePaul University before leaving to focus on Lyrical Lemonade. His music videos, which he uploaded to YouTube, were known for their vivid colors, kinetic pace and “squiggly” line animations.
An early standout was the video for Warhol.SS’s “Speed Racer,” in which the rapper appeared to shrink down to the size of toy cars.
“I just trust his vision,” said Warhol.SS, 28, who grew up in South Shore and now lives in Atlanta. “He’s one of the only people that could tell me to do something that I think might be a little corny, and I’ll still do.”
Warhol.SS was featured on the bill at Bennett’s inaugural Summer Bash at Portage Theater and will return to the city this weekend to perform at Summer Smash. He praised the event for helping to popularize SoundCloud-era rappers outside of Chicago, from Playboi Carti to Lil Yachty.
“It’s more than just a festival,” Warhol.SS said. “It introduced the underground to the mainstream.”
Making Eminem breathe fire
Bennett went on to direct videos and executive produce content for some of the most famous entertainers, including Jack Black and Will Smith. But his first video for Eminem, 2020’s “Godzilla,” was a turning point. With access to a large budget for visual effects, Bennett suddenly had no limitations on his creativity.
“I was like, ’I can do anything?’ Bennett recalled. “‘He can breathe fire? His mouth can fall off? I can have 3D Godzilla figures behind him and we can have floating knives? I want it all.’”
Today, Bennett has slowed the pace of his music video production, giving other directors opportunities to create content for Lyrical Lemonade, which has expanded to include merchandise and a digital content series. In addition to his film projects, he also designed a new Birkenstock shoe, his signature footwear, which will be released later this year.
But he said he will always direct music videos, even though audiences are engaging with them differently.
“Now, it’s less about being a discovery tool for artists, and it’s more so about feeding your fan base,” he said. “A lot of artists are now investing in music videos to communicate with their fans and to give them something that they can digest as a source of entertainment.”
Now, if Bennett takes on a music video, he said it must pull him out of his comfort zone.
That seems to be the case for most projects.
“Anything that challenges me to try something new,” he said.