Cole Bennett needs no introduction. This is just pro forma.

A music video director, record executive, creative director, festival director, filmmaker, and more, Cole Bennett has been shaping the visuals that accompany our music for over a decade. Lately, he's shaping the music too.

Many know the story: from Plano Illinois, a high school dropout, a kid with a video camera. Bennett founded Lyrical Lemonade as a blog, and uploaded whatever music videos he made there. He came of age alongside the first Soundcloud class to graduate into the mainstream. Many of the iconic videos of that era are his doing.

Bennett's talent and make-do philosophy kept propelling him, and today he's worked many of music's biggest artists. It's also become more than music videos. The Lyrical Lemonade Summer Smash Festival is the premier music festival of Chicago's summer. All Is Yellow is Lyrical Lemonade's debut studio album, and Bennett's first time executive producing a project of this scale.

As the hats multiply and get heavier, Bennett is transitioning into a new phase of career. He'll still direct select music videos (Justin Bieber's Yukon video is a recent example), but is now employing a roster of directors to handle much of the day to day work. He's setting his sights on narrative film, and is in the process of learning the skillset.

We spoke to Cole Bennett about a lot of stuff, trying to get a sense of what it feels like to be on one mountaintop while searching for the next one. Read on.

-

Welcome: Take us through a normal day-in-the-life, if you can remember one.

Cole Bennett: Wake up. Check my phone (working on not doing this). Drink a glass of water & some brekky. Play with my dog. Call/see my mom. Write. Read (If I’m really on my A game that day). Edit. Zoom calls if I’m feeling business savvy. Workout if time allows. Eat a nice meal. Watch a movie with my girlfriend. Take some melatonin gummies and fall asleep. Repeat.

Welcome: What’s a formative childhood event? Something that occurred that you believe may have been a necessary step for you arriving here today?

Cole Bennett: My dad passing away. It’s all I ever knew & I think it made me grow up faster & slower all at the same time. It taught me how to use my imagination. Ultimately a big help in leading me to where I am today.

W: Do you remember any particularly impactful music videos you saw as a youth? What were they, and why were they impactful?

CB: ‘Drop’ by The Pharcyde. Arguably one of the most impactful music videos of all time. Another one that I’ve mentioned before, ‘America’ by Mac Miller, Casey Veggies & Joey Badass. Honorable mention: My Chemical Romance, ‘Welcome To The Black Parade’. I’ll never forget watching this for the first time ever. Not sure why this one stuck with me so much, but it did. MySpace era. Better times.

What influence, if any, did early drill videos have on your cinematic sensibilities?

Drill videos taught me how to think quick. Imagine adjusting your iso with a gun pointing right into your camera. I learned a lot on the spot. If I could go back I wouldn’t change a thing.

This many years on, people still disagree about the nature and definition of ‘Soundcloud rap.’ What were the defining characteristics of that era to you? What was special about that moment in music?

To me, the SoundCloud era was about just putting your art out and having fun. First week numbers weren’t a thing that people cared about yet. Artists had less pressure on them to meet unrealistic expectations. Everyone knew everyone. It kinda felt like high school.

You only direct a select few music videos a year now. How do you pick which projects you want to take the reins on?

I like to work on projects that allow me to try out new things. I really want to learn something new on every video I work on. If I feel like I can do that, then I’m in. I have a long list of ideas that I want to execute creatively, sometimes I listen to a song that pairs perfectly with one of them. Those are my favorite types of projects.

Talk to us about the roster of directors you're bringing on to Lyrical Lemonade. What do you look for in directors?

Currently we have two directors signed under Lyrical Lemonade - AMD & Diamond. We are about to announce our third next month. I’m just looking for directors who love what they do. I want people who creatively thrive when they’re uncomfortable. I’m looking for leaders & risktakers. I want to learn from them just as much as they can learn from me.

What do you think about the state of the contemporary music video? We’re seeing a new wave of DIY aesthetics permeating the UK underground, which feels exciting.

I’m loving everything that is happening right now. Feels like there is a resurgence of creativity happening right now in music videos. You never needed fancy equipment less than you do right now. All you need is creativity and a very solid work ethic.

What about the state of contemporary music as a whole? What is exciting you right now?

People taking chances and blocking out the imaginary noise. That excites me. We can’t forget that this is supposed to be fun above all else. Che is exciting to me. Feng is exciting to me. Thirteen Degrees is exciting to me. Jimothy Lacoste is exciting to me. Bb trickz is exciting to me. Smokedope2016 is exciting to me. Sienna Spiro is exciting to me. There’s a lot more, but those are top of mind in this very moment.

You’ve said elsewhere that as you worked on All Is Yellow you started to see how the craft of building a song relates to that of building a music video. What else did that project teach you about making music?

That project taught me to just try things. People may hate it or love it, but you just gotta go for it. It taught me that just about anything you’ve ever felt or experienced can be translated into music. It was a really fun process.

Is there another album in the works?

Probably one day. I’d maybe call it “But, I’m Feeling Blue.” I look back at that whole experience and smile about it all. It was a lot of work, but it was so much fucking fun. I’ll hold those memories with me forever.

Music videos and video content more generally has the potential to be impacted by new AI video tools. How do you navigate the use of these new technologies? How do you see them impacting the video industry today? What about in the coming years?

Man, that’s a good question. I’m really fascinated by AI. I see both the pros and the cons. It’s going to greatly impact everything, for better and for worse. I’m excited to see it unravel, because we honestly don’t have a choice at this point. It’s here. I’m looking forward to seeing all the ways that it can be used for good.

As you shift towards a new form of filmmaking, you’ve mentioned the necessity of becoming a student again. What does that studentship look like for you? How are you studying this new craft?

Reading a lot. Watching a lot of interviews, tutorials, classes, etc. Getting my reps in. Writing screenplays & reading screenplays. Making short films. Putting myself in the narrative frame of mind. I’m almost ready for the real thing. Just a few short seasons away.

How has your creative process changed as you’ve moved to this new medium of film?

It’s taught me that it’s all about a good story. You can make the most beautiful looking film, but if the writing falls flat then it’s just eh. I guess it’s all subjective at the end of the day. You can get away with a lot in music videos. Not so much with narrative pieces.

Who are some directors you look up to? What are some movies that have been inspirational for you?

Stanley Kubrick, David Lynch, Spike Jonze, Sean Baker, Harmony Korine to name a few. Tangerine & The Florida Project by Sean Baker have really been speaking to me as of late. Those made me feel something.

How’s the Chief Keef doc coming along? How did that project come to be?

It’s coming along really great. There’s a lot of moving parts when it comes to working on a piece like this. I’m learning. It’s very beautiful. We are taking our time with it.

What was the thought process behind the inception of Summer Smash? How did you plan on differentiating yourself in the festival industry?

I used to sneak into festivals in Chicago when I was younger. We’d jump the fences every year. I remember running into the crowd and feeling so free. I wanted to create that same experience for others. Maybe minus the sneaking in part, but I respect the hustle. I threw my first LL show in 2013 at a 90 person venue in Chicago. From there I always dreamt of one day throwing a festival, I just never thought it would end up happening. Then it happened. Now we’re going on year 8 which is absolutely crazy. The goal is to bring people together for a one of one experience. Not just the attendees, but also the artists. I love that Summer Smash has become a place where artists can come together and meet each other. That’s my favorite part of it all.

What is your favorite video you’ve ever directed?

YUKON by Justin Bieber. Maybe it’s recency bias but I don’t think so. This video was so pure and natural. We went on a trip with our girls for a few days and I brought my camera with. I had no idea what I was going to capture or if we were even going to end up shooting a music video. It all happened so quick. Felt like old times. That one is really special to me. For many reasons. Justin & Hailey have such a beautiful love & family. Honored that I was able to capture such an intimate piece for them to have forever.

Between the videos, the lemonade, the festival and more, how do you manage all the ventures on your plate?

It’s a lot. Every week I snap in and out of what I choose to prioritize. It’s all not possible with the army of people behind it all though. I have one of the best teams you could imagine. We work together like one big family. No task is too big for us.

As your team scaled beyond just you producing the videos from start to finish, what have you done to maintain your vision on projects?

Leading a project and bringing it home is one of the most satisfying feelings in the world. I used to feel really iffy about the idea of delegating because I wanted to be in control of everything. It took me years to open up to the idea of me not operating the camera on every shoot. As I’ve gotten older, I realized to truly be in control of your vision is to delegate. That’s how you learn to lead the ship to the promise land. I’m still learning. It’s fun.

Are you still planning on opening up an amusement park?

One day, yes. I have so many plans. So many dreams. One at a time though.

In your music video work you’ve sometimes had to convince artists to try things they normally wouldn’t. For example getting Chief Keef to actually wear a suit on camera. How do you navigate those conversations to bring artists into your creative vision without pushing them too far? Has that process gotten easier now that your track record speaks for itself?

It’s just about knowing when to go for it or not. There’s a thin line between “it doesn’t hurt to ask” & making someone uncomfortable. It’s up to you as a director & collaborator to know when to ask these questions. You just need to feel people out. The Chief Keef wearing a suit situation was definitely one of those “it doesn’t hurt to ask” scenarios. There was another time I remember asking Roddy Ricch if he would cheers a champagne glass in a music video and he looked at me like I was crazy. I didn’t think that was a wild ask, but I guess you never know.

What are some movies/shows/media that have influenced your music video aesthetic?

It’s really all just a feeling. I’m inspired by color palettes. The Simpsons color palette helped inspire the Lyrical Lemonade color palette. Growing up is exciting though, your taste grows and evolves as well. I generally like more muted combinations as of late, but every project calls for something different. That’s the fun part. You never know what may speak to you.

What do you do in moments of creative block?

Watch a movie or spend some time with friends and family.

How do you manage not burning out?

You can’t work 24/7. I work a lot, but not every second of the day. I allow myself time to recharge. I used to work nonstop and it would result in me putting projects out that I wasn’t always proud of. I used to really not sleep. When Lyrical Lemonade was really taking off, I would sleep maybe 2-4 hours a night. I really put my all to it. I wouldn’t go back and do it differently but it was definitely super unhealthy. I used to think that shit was so cool though.

Your definition of success must have shifted from when you first started. How do you define success now?

Happiness.

Paint us a picture of what you hope the Cole Bennett of ten years from now will be working on, and the impact you aim to have on culture by then.

I will have put out a movie out by then. Maybe a couple. I’ll probably have a kid. Maybe a couple. Who knows. As long as I’m happy, I’m good. Hopefully the impact I will have is inspiring people to just go out and do what they love. You’re never too cool to try.

-