Hip-Hop Video Director Cole Bennett on Working With Lil Skies and Lil Xan & Why He's Tired of the Term 'Underground'

Cole Bennett
Brooklyn Wheeler

Cole Bennett

Plano, Illinois -- population 10,856 -- is such a quintessential Midwest town that in 2011 the producers of the movie Man of Steel chose it to double as Superman’s boyhood home of Smallville. That cinematic moment was such a point of pride for the community that every summer the town briefly transforms back into its alias, for a three-day “Smallville Superfest.”

Truth be told, though, Plano actually has produced a Superman -- at least in the hip-hop world -- in the form of Cole Bennett, who four and a half years ago, as a senior at Plano High School, founded the blog Lyrical Lemonade, and has since gone on to become to the DIY hip-hop universe’s biggest and busiest videographer.

Bennett is insanely prolific -- by his own estimation, he’s directed more than 300 music videos to date. He’s also incredibly resourceful, able to turn a no-budget clip shot in an Airbnb in Los Angeles into Lil Pump’s huge “D Rose”; letting Ski Mask The Slump God run around Times Square with a Chucky doll in the memorable “Catch Me Outside”; recently pairing Georgia’s 6 Dogs with a giant rabbit for “Butt Cheeks”; and last year bathing Lil Xan in blue light for “Betrayed”, the breakout artist’s monster video that’s logged, as of this writing, 133 million views and counting.

And that blog he began in high school? Lyrical Lemonade is now a website, event promotion, artist management, merchandising and production company that’s an essential part of Chicago music. All that from a guy who doesn’t even turn 22 until May.

Bennett got a chance to return to his roots -- Plano High -- in the fall, melding his past with his present when he used his alma mater as the setting for “Nowadays,” a Billboard Hot 100-scaling jam from two of hip-hop’s hottest young names, Lil Skies and Landon Cube. Though the song became a hit, the experience wasn’t without its fraught moments. Below, Billboard discusses that shoot with the video maker and entrepreneur, along with how  Bennett decides who to work with, the term “underground," Lyrical Lemonade’s upcoming fifth anniversary, and its place in the Windy City media landscape.

Cole! Belated congratulations on another amazing year, and your new offices. And you guys just recently launched a new interview series, with Lil Skies as your first guest.

Yeah, we moved into the space in November. And I wanted the new Lyrical Lemonade Interview series to kind of introduce the new space, and introduce that trademark, the Lyrical Lemonade sign, and create interviews that are timeless content for people to watch and be inspired. I kind of want this space to be like a hub for Chicago, when artists come into town for tour or whatever it may be -- I want Lyrical Lemonade to be the place you stop by.

On the site you guys regularly link to interviews from Hot 97 or No Jumper and others. Now that you have your own series are you in a sense competing with those guys?

Not at all. I try not to believe in competition. I will still continue to post the Hot 97’s and No Jumper and Montreality -- I watch those. I think it’s all great content. And I get inspired. I don’t really try to compete. And, you know, No Jumper -- that’s L.A., and they do a great job and kind of create a culture for L.A. And Hot 97, that’s New York. When you’re in New York, you want to stop by Hot 97. And Montreality, they kind of bounce around. You know, Nardwuar has, I think it’s Vancouver. And I think it would really be cool to create that culture in Chicago.

There’s so many young artists you’ve worked with that have blown up to one degree or another, and none hotter at the moment than Lil Xan. “Betrayed” just recently became your most-viewed video ever, with 133 million views. How did you end up working with Diego?  

I met Xan about a year ago. Our buddy Robesman -- he’s involved with the No Jumper podcast, super cool dude -- he loved Lil Xan. He did a collab t-shirt with Xan, he was really pushing him when a lot of people weren’t giving him a lot of attention. So I met him at a studio one night -- Robesman actually made a vlog of it that’s on YouTube -- and then we just stayed in touch. I knew Xan made good music, but I really didn’t know the substance of it all.

And with the name, and Xanax being the drug of the quote-unquote “Soundcloud rap” and all that bullshit, I just knew the media’s outlook on things. But then I was in L.A., and he sent me “Betrayed”, and I listened to it and thought, “This song is crazy! No one’s gonna expect this, with this kid’s name.” It had a whole different meaning than what people would think. It was actually an anti-substance thing. So I was super down to shoot it. And the colors in the room just fit so perfectly, that blue ambiance and the kitchen with the microwave -- it just had a dark feeling.

Lil Skies and his cohort Landon Cube are also breaking out in a major way 00 thanks, in part, to the videos you’ve done with them, one of which was “Nowadays” from Skies’ mixtape Life of a Dark Rose. And for that one, you went back to your high school?  

Yeah, this is actually the best story. I called up one of my high school teachers and said we wanted to shoot in the school, and he said, “We’ll take care of it. You’re good to go.” And so I planned everything out, I went and got the letterman’s jackets for Skies and Landon. And we were originally gonna do another song off the mixtape, “Big Money," that’s what the treatment was written for. But I had a feeling about “Nowadays.” I thought it could be big, and also the setting and this treatment, I felt like it fit “Nowadays” more than “Big Money." And also, I was like, “I don’t want to upset the school, I feel like ‘Nowadays’ has a better message to it."

I was like, “Man, we gotta do ‘Nowadays’. Landon’s out here, we can use him for more than just a cameo. Let’s give him his shine...” But then they called me back and they said, “The label is saying, 'No way, we already have the treatment and everything is set for "Big Money." We gotta do "Big Money."'” And I was like, “You know what? I’ll pay for this out of my pocket. We’re doing ‘Nowadays.’ I don’t give a fuck. Cancel the budget. I have a feeling about ‘Nowadays’. We’re doing ‘Nowadays.’” So we shoot it throughout the school, everything is turning out perfectly, all the shots look amazing, I’m walking through my old high school that I haven’t been at in like two years... It was really cool and sentimental, but fun.

But then like the next day my teacher called me, and was like, “The school is saying we need to not reveal anything of Plano High." I guess a cop walked in and he smelled marijuana. And I was like, “Well no one had it -- maybe someone smoked before they went there, but obviously we have respect for the school. It’s not like that.” But beyond that it was kind of the idea of a kid having face tats, I think. I don’t think they were familiar with the artist, and I didn’t tell them about the artist, I just said we were shooting a music video. And my teacher said, “We’ll be fine. We just need to show as little of Plano High School as possible.”

So it was fine?

Well, no. Because then, before I had edited it, I was in Europe on tour with Ski Mask, and my teacher was blowing me up on my phone saying, “We can’t release the video. This can’t come out. We had a meeting with the school board, and everyone voted it down.” So I landed back in Chicago, and I typed up this three-page counter argument for every argument they could try to use about everything. Because I knew how big this was gonna be, and I knew how harmless it was -- and keep in mind, they hadn’t seen any of the footage, or heard the song at all.

So I go there, I was speaking with the two top people in the school district. And I was excited, because I was ready to answer anything they might have. But they were like, “What would you think if you were a parent and you were thinking of putting your kid in Plano High School, and you saw a rap music video coming out with a kid with face tats walking down the hallway?” And I was like, “What is going on? That’s the most stereotypical thing I’ve ever heard.” I was like, “You guys haven’t seen the content, you haven’t heard the song.”

I had all the lyrics for them. I had examples of songs that we would play in high school, for the basketball teams, or football, I talked about the meaning behind AC/DC songs, that they were about prostitutes, cocaine and shit. And I was like, “This just isn’t making sense!” And they said, “Well the board voted it down.” I was in there for literally two and a half hours, hours fighting it and fighting it. And then I was like, “You know what? Fuck this. This is the most ridiculous thing I’ve ever heard in my life." I literally told them, “This is absurd.” So I went home and I thought, “Something about this isn’t making sense.”

And I looked into it, and I found out that you need to have a public board meeting to make a decision like that. And they hadn’t had a public board meeting, they just spoke about it together. The next board meeting was like December 20th or 22nd, and I was like, “Damn, I need to put out this video before that next board meeting, so they can’t legally ban this video.” And I was like, “I’ll face the consequences when we get there, but I know I’m not doing anything wrong.”

It was a Sunday night, and I think they had like three days of school before they went on winter break, and I wanted to release it Sunday so that all the kids at the school could be talking about it on Monday... so that all the school board members could hear how excited all the kids were. ‘Cause I knew how impactful it was, ‘cause that’s inspiration! It’s a very small town, so to see these kids’ favorite rappers in their high school, and now the song’s on the Billboard Hot 100 -- that’s crazy! And I don’t think the school sees all the benefits of it, but they saw it as, “Cole Bennett’s doing a video here and in the past he’s had videos with guns..." And I was just, “At Lyrical Lemonade we have a positive message. My previous videos have no reflection on what I’m bringing to your school."

But anyway, released the video, the school said nothing. It did a million views in like, 20 hours. And I never heard anything from the school, and I’ve only gotten positive feedback.

That’s quite a story. So are there any limits to the things you will depict in a video, in the age of #MeToo? I notice the butts were blurred out in 6 Dogs’ “Buttcheeks”.

Well with “Buttcheeks” I wrote in the treatment that I wanted their butts blurred out, cause that was actually a spin-off of an old Blink-182 video, of them running down Hollywood Boulevard just butt naked and pixelated, blurred out.

But usually anything an artist wants to incorporate into a video, if they bring it into the video, then they’re fine with it being in there 100 percent -- like, whether it’s them holding a gun, or them with a girl or whatever. Obviously, there’s times when I will step in and say, “Maybe this doesn’t make sense.” And you do have to be aware of your brand and your company and what you put your name on, because it’s a representation of you in a sense. But it’s really just the two heads coming together.

You’re in a position now where you’re also getting calls from huge stars -- you did the Migos tour video last year. But I would imagine you’re in a position now where you have to say no to people pretty often, if only for scheduling. Are you choosy about who you work with, either based on the music, or whether you have creative control?

Yes, all those things. First and foremost I have to like the music.

So you’re not gonna take a job that pays you $100,000 just because of the paycheck?

Literally no way. Because it would feel miserable. I wouldn’t want to do it and I wouldn’t feel connected to it. And I want to feel connected to everything I do. For me, yes, I want to work with legends -- you know, people I looked up to growing up and people that kind of shaped my taste in music. Like when I got the opportunity to work with Mac Miller and Carnage [“Learn How To Watch It”]. That was something big for me, that I really wanted to do. When I got to shoot for the Migos, that was incredible. But then I like shooting with a lot of younger guys, that’s fun for me. It’s really just about what I like.

What do you think of media continuing to refer to this word that you’re a part of as “underground”? It seems to me when you’re doing millions of streams and 120 million views, that’s not underground.

It’s time to really say goodbye to that, all of the standards in the industry and all the bullshit about how things are “supposed” to be and this and that. If you look at the Billboard Hot 100 right now -- I don’t have it pulled up in front of me -- but that’s definitely a gauge of what people look at as relevant or quote-unquote “mainstream” or what’s doing well in the music industry. And there’s multiple so-called “underground” artists that are on that list.

I think people identify underground as being more based on the approach to things. So, if an artist is dropping his videos on World Star or I do a video with them, or their biggest song is on SoundCloud, or they have a different way of marketing themselves -- then they’re “underground.” But if an artist pops out of nowhere and starts collabing with big artists and has a Vevo channel, well, then they’re “mainstream.” You know what I mean? It’s kind of like the structures that we identify as underground or mainstream.

Also radio play is a big factor. For instance, someone like [YBN] Nahmir or Skies -- they’re not all over the radio right now, and I feel like a lot of people still determine what is mainstream by the radio. For whoever still even listens to the radio, you know what I mean?

Do you feel like you’re in a sense an ambassador for Chicago, a city that’s had a lot of negative headlines in recent years? On your Twitter page it says, “Chicago Now, Global Soon.”

For me, if it wasn’t for Chicago, I wouldn’t be in the position I am in. I started getting into everything by listening to a local Chance the Rapper, and a local Chief Keef and a local Savemoney crew and Alex Wiley and Mick Jenkins. That’s what got me into all this. So yeah, there’s been a lot of negative press and representations of this city, but there’s so many great, great things that Chicago has to offer that people don’t get to see inside of. Kind of the starting point of Lyrical Lemonade was trying to build a culture in the city, and now it’s trying to show other parts of the world what is going on in the city.

Your five-year anniversary is coming up in September. Are there any big plans? A Lyrical Lemonade tour?

We are working on a tour right now, a small major-market tour -- a five to six-city tour. But you’re actually the first person that mentioned that it’s the five-year anniversary. I wasn’t really thinking about that. But now you’re gonna have me planning for it! Thanks to you, I’m gonna start looking into that.

A version of this article originally appeared in the March 10 issue of Billboard.