The Bigger Picture
Cole Bennett has become the foremost music video director for a new generation of rap stars, all while the game’s lauded vets hit his line. As his Lyrical Lemonade empire flourishes, the pursuit of happiness reigns supreme.
Words: Georgette Cline
Editor’s Note: This story originally appeared in the Summer 2021 issue of XXL Magazine, on stands now.

Cole Bennett can finally say he made it, and a tweet from Kid Cudi at 2 a.m. set it off. Nearly 10 years after Bennett launched his Lyrical Lemonade multimedia company in 2013, the lauded music video director’s dream came true when Cudi requested that Bennett direct a video for him. All through the late night on a Monday in March, manifestation was happening right before Bennett’s eyes.

In 2018, he tweeted, “Kid cudi is my favorite artist of all time.” A seventh grade Bennett “fell in love with” the Ohio-bred rapper’s 2008 mixtape, A Kid Named Cudi. Then, at the end of 2020, Bennett wrote on Twitter, “The day I work with cudi will be the day I will be able to truly say I made it.” Over the years, Bennett tried contacting the Ohio-bred rapper and even tweeted him directly to no avail. Finally, words became reality when Cudi sent the tweet five months ago that would ultimately kick off a working relationship with Bennett to create a visual for “Tequila Shots,” featured on Cudi’s 2020 album, Man on the Moon III: The Chosen.

“I didn’t even go to bed that night,” Bennett, 25, recalls of the moment he saw Cudi’s message, as he sits inside his Chicago headquarters via Zoom. “And I was just so excited and to be working on something off of a Man on the Moon III, which, you know, Man on the Moon I and II, like such big parts of my life… And it does make me realize manifestation is a very real thing and the world works in wonderful ways when you just speak it into existence.”

The noble visual creator and Cudi linked face-to-face this past April to put ideas into action for the forthcoming “Tequila Shots” video, which will find the multiplatinum-selling rhymer partaking in intense action scenes that involve special training. The moment is a career-defining milestone for Cole Bennett, who has become the foremost music video director for both a new generation of rap stars including the late Juice Wrld, Polo G, Lil Tecca, Ski Mask The Slump God, Cordae and NLE Choppa, among others, and established hip-hop veterans like Eminem. Think zany special effects, a by-any-means-necessary filming style, playful animation and storylines that are nostalgic, comical or mind-blowing depending on the artist. A self-proclaimed “big kid at heart,” that energy permeates Bennett’s work.

Cole Bennett’s growing Lyrical Lemonade empire houses a well-respected YouTube channel with around 18 million subscribers and almost 400 videos, ranging from rappers’ official music videos to interviews with rising artists and yearly reels flexing Bennett’s directorial chops. It’s become the go-to spot for new music discovery. A media outlet, merch, live events business that includes the Summer Smash festival, fulfillment company, a lemonade beverage, his Chicago H.Q. nicknamed “The Space,” partnerships with Jordan Brand and a trademarked animated figure called Lenny have also attributed to Bennett’s company’s accomplishments up until this point. The sweet taste of success all started with a love for hip-hop and a blog.

After being introduced to 50 Cent and his music by one of Bennett’s older sisters, a 7-year-old Bennett convinced his mother to take him to the store to buy him the rapper’s Get Rich or Die Tryin’ album. She raised three children as a single mom once his father died by suicide when he was 2. “I think that’s where my work ethic comes from,” expresses the Plano, Ill. native, who cites Rick Rubin as a mentor and regularly feels inspired by their meetings. “I got to see my mom work literally three jobs.”

As the years progressed, Bennett became a huge fan of Lil Wayne. Then he got put on to Gucci Mane, Shawty Lo, Wiz Khalifa, Mac Miller, Kid Cudi and Chance The Rapper, the latter of which led Bennett into discovering more artists in the Chicago rap scene and “getting to where I’m at now” with his passion for video.

“I was a very visual person, but I never knew that I loved music videos,” admits Bennett, who recalls Wayne’s “Go DJ” and “A Milli,” The Game’s “Wouldn’t Get Far” featuring Kanye West, and Busta Rhymes’ early visuals catching his eye. “I always had this idea since I was super young of what it would look like if I made a music video. I was 8, and was like, if I did a music video, it looked like this and it would be like a Nike Air Force One… It would be on a white backdrop and like the Nike sign would just, the color of it would change with the beat.” Bennett’s “just do it” attitude toward creative ideas has trailed him throughout his life.

cole bennett photo music video director
Kevin Maya

A high school multimedia class during his sophomore year sparked Cole Bennett’s video directing flame. At the time, he was in tune with the underground Chicago rap scene after listening to Chance, Vic Mensa and Alex Wiley, and wanted to start making videos for artists. He encouraged his friends to make music so that he could practice creating accompanying visuals. A year later, as a high school junior, Bennett launched the Lyrical Lemonade blog to showcase his love for Chi-Town hip-hop. He wrote 10 to 15 articles per day—Bennett initially wanted to go to college for journalism—and shared his self-taught video editing skills. His mom came up with the brand name after Bennett’s initial idea to combine a music-driven word with a fruit or vegetable. The first video on the Lyrical Lemonade YouTube channel—after Bennett deleted the first five—is Bnova’s “Call of the Wild,” which Bennett crafted by using shots of nature, fireworks, the city of Chicago’s famed skyline and insects that pulse on screen to the producer’s beat.

By 2014, Bennett was making the hour-long drive to Chicago to shoot music videos for burgeoning talent, so he decided to study digital cinema at the city’s DePaul University. Early on, Bennett filmed clips for artists who paid him $20 and did interviews for Lyrical Lemonade in his dorm room between classes. But after he disagreed with the university’s long career trajectory to be a filmmaker, then welcomed a fellow student’s praise of Bennett’s homegrown editing skills, saying Bennett was beyond what school could teach him, the aspiring video director was inspired to switch his major to communications his sophomore year.

Bennett’s first big break as a music video director came in 2016, when he filmed Chi-Town rapper Famous Dex’s “Hit ’Em Wit It” video. Shot in the basement of Dex’s Inglewood home, the final visual features Bennett’s colorful animation outlining Dex’s face and body movements as the artist and his friends dance around the crib and flash lots of cash. “Without Dex, I really don’t know where I would be,” Bennett admits. “He really helped allow people to see my vision and we got to make something beautiful together.” The Lyrical Lemonade channel had roughly 120 videos before “Hit ’Em Wit It,” now at over 20 million YouTube views, took off on the internet.

“He a smart guy, he has a great and cool vision and I love him and that’s my brother,” Dex says of the friendship. “Cole’s the best. That’s why we work good together.”

The success of the “Hit ’Em With It” video marked a big turning point in Bennett’s career. Other Windy City rappers like Lil Bibby, King Louie, Katie Got Bandz and started hitting up Cole to collaborate. Smokepurpp and Xavier Wulf hit his line, too. Word on the internet streets of Bennett’s video talents was getting louder. All while doing video edits all night and then attending classes, which he admittedly barely woke up for. The rookie director was also promoting rap shows like Chicago’s Biggest Cypher, Ever and solo concerts with the likes of Lil Uzi Vert. Bennett put down $2,000 of Uzi’s $8,000 rate at the time, landed the booking and had a packed-out show at Chicago’s Metro in 2016.

At that point, Bennett had to choose: college or Lyrical Lemonade. He wrote out a short list of goals for Lyrical Lemonade, achieved them and dropped out of DePaul University in 2016. “I accomplished all of them and I just never looked back since.” A wise choice considering he’s racked up more than 7 billion video views total and received several BET Awards nominations so far. Though there are downsides to the job. Bennett once spent 200 hours editing a Migos video that never saw the light of day.

One good thing to come of Bennett’s college experience is meeting Sal Tarantino, Lyrical Lemonade’s executive producer. The 25-year-old Waukesha, Wisc. native was Bennett’s roommate at DePaul, where Tarantino studied finance and real estate. When Bennett’s Lyrical Lemonade email inbox started to get too overwhelming, he enlisted Tarantino for help, and the rest is history. Tarantino is currently one of 12 employees at Lyrical Lemonade and known Bennett for six years. He takes on any job necessary at the company: administrative work, booking video shoots, creating invoices, coordinating teams and devising budgets.

Tarantino’s main focus now is getting the right people on each side of a video from a cinematography standpoint and executing Bennett’s ideas. Having an animal wrangler monitor an ostrich on set for Ski Mask’s “Faucet Failure” video, finding a grave digger for Gnar’s “Death Note” featuring Lil Skies and Craig Xen, and navigating a swamp for Juice Wrld’s “Bandit” featuring YoungBoy Never Broke Again, each released in 2019, are all part of Tarantino’s producing duties.

Think of Tarantino, a former accounts payable/receivable clerk at a senior living facility, as the Lyrical Lemonade steward, a servant to the crew so that they can showcase their talent to the best of their abilities. “The most powerful thing that Cole brings to the table is coming together with the artist and making a moment,” affirms Tarantino, who calls the director a “charismatic, passionate leader.” “We’re always just trying to make it happen, any means necessary. Producing is a solution-based position.”

“None of us are experts at what we do,” Bennett adds. “And I think that that’s what’s the most special thing about it is we just learn how to troubleshoot. We learn how to figure it out.” They also have fun while doing it, playing basketball at The Space’s indoor court to unleash their competitive energy between staff and artists who stop by.

With hundreds of music videos in the can since Bennett started directing full time five years ago, picking a standout is never easy. Ski Mask's spur-of-the-moment Times Square jaunt for “Catch Me Outside” in 2017, with over 134 million YouTube views— “I remember feeling so accomplished and impressed with myself”—Juice’s European performance trek for “Armed & Dangerous” in 2018, with over 210 million views— “We’re out of the country and Juice is becoming this superstar out of nowhere”—and Eminem’s trippy department store visit for “Godzilla” featuring Juice in 2020, with over 378 million views— “When I wrote the treatment, it was eight pages and it was all writing, there was no reference images”—are among Bennett’s beloved creations for different reasons. “My creative expression is very important to me,” he maintains. “It’s what keeps me happy, motivated and inspired.”

Bennett, who also directed Eminem’s “Gnat” visual last year, refuses to relinquish creative control of Lyrical Lemonade despite two $30 million-plus offers in different areas thrown his way in the last few years. “A lot of people find it hard to believe that I’ve never seen a million dollars in my bank account,” says the visionary, who rocks Birkenstocks on the regular and packs SpaghettiOs when traveling for his next video shoot. “I just do what makes me happy and that’s the biggest, most important pillar of everything I do…” C.R.E.A.M. isn’t a way of life in his world.

As he looks ahead at what’s next for the Lyrical Lemonade brand, the lemons are being squeezed back into the empire. There’s the third annual Summer Festival in Chicago with headliners A$AP Rocky, Lil Baby and Lil Uzi Vert this August; a book, to be released via Penguin Random House next year, that Bennett is writing about his creative journey in hopes to change people’s lives the same way others have done for him; the Lyrical Lemonade beverage being sold in 7-11 convenience stores, a limited edition Pop-Tarts Lyrical Lemonade Toaster Pastry available at the Pop-Tarts x Lyrical Lemonade Experience merch event in L.A. on Aug. 13, the Pop-Tarts Lyrical Lemonade box for sale on the brand website on Aug. 14 and new videos, of course. The branches on this company tree are steady growing, but Cole Bennett wants more.

Pop-Tarts lyrical lemonade

“I’m aware of the impact Lyrical Lemonade has, and I’m aware of the eyes that it has on it, and I’m very thankful for that,” he asserts. “But, I think there’s always so much room to grow in every area.”

Let the creative juices flow.

cole bennett photo music video director
Kevin Maya

Check out more from XXL’s Summer 2021 issue including our Freshman Class cover interviews with 42 Dugg, Iann Dior, Coi Leray, Pooh Shiesty, Flo Milli, Morray, Rubi Rose, Blxst, Toosii, Lakeyah and DDG, producer Nick Mira's thoughts on producing the beats for the Freshman Class, an in-depth conversation with Ski Mask The Slump God about his comeback this year, Moneybagg Yo's candid discussion about his new music, family and indie labela look at what the 2020 XXL Freshman Class has been up to since last year, Doin' Lines with Jack Harlow, Lil Tecca speaking on what to expect from his upcoming We Love You Tecca 2 albumand more.

See the 2021 XXL Freshman Class

Welcome 42 DuggIann DiorCoi LerayPooh ShiestyFlo MilliMorrayRubi RoseBlxstToosiiLakeyah and DDG to the 2021 XXL Freshman Class.

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