- Druski spoke to Insider about developments in his acting and comedy career and recent entrepreneurial efforts.
- He discussed venturing into stand-up comedy and film and getting industry game from Drake and Kevin Hart.
Early last month, I spoke to Druski at an inflection point in his career as an actor and comedian.
In a Zoom call, he discussed the evolving variety of his comedic work, including the Instagram Live show for his satirical record label, “Coulda Been Records,” and the guidance he’s gotten from the likes of Kevin Hart while venturing into stand-up comedy.
This week, he announced his first headlining tour, a 30-city run called the “Coulda, Woulda, Shoulda” tour, which tickets are on sale for now. The shows will combine traditional stand-up and segments of live participation from aspiring entertainers, taking the “Coulda Been Records” IG Live show to the stage.
In our conversation, Druski discussed his recent entrepreneurial efforts, including ownership stakes in a Fan Controlled Football League team called “The Shoulda Been Stars” and in Happy Dad Hard Seltzer. Among other topics, he also reflected on the industry advice he’s gotten from Drake and previewed the coming Tina Gordon-directed and Will Packer-produced film “Praise This,” which he’s starring in alongside Chloe Bailey and Quavo.
This interview has been condensed and edited for clarity.
Wanted to say off top, great respect and appreciation for your work across the board.
Definitely. I appreciate that, brother. Means a lot.
As someone with ADHD, I really respect the prolificacy.
[Laugh]. Yeah.
What’s been the key for you in staying consistent with your creative output?
Honestly just me constantly thinking about what could be done or like who else is working, you know what I’m saying? I always catch myself in moments of just sitting and thinking like … I don’t know, it’s just a weird feeling I get. Like I just can’t imagine falling off or having a short career, or just not being that number one go-to guy for comedy, you know? So I think that’s what keeps me going and what keeps me more motivated than anything.
I gotta say, the Coulda Been Records sh-t kills me.
Yes, man.
I’m biased toward that type of humor. Do you personally get more out of that than the sketch material at this point? Or how do you view those two modes?
Like … explain further? Lemme see.
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Like the IG Live versus doing sketch. How do you view those two at this point?
Uh, very different. Doing live shows in front of fans is very different as well. I think the difference is, honestly, your improv game has to be on a thousand when you’re live in front of anybody. So when I do Coulda Been Records, everything is like 100% improv. Nothing is written. Nothing is already set up to say. Everything is just off the top of the dome, you know? So I think that’s just me showing different ways I can be funny. Improv is a huge thing in comedy, and I think it’s needed, you know what I’m saying?
So it’s just me showing off my skills, and how good I am just off top. Sketch is pretty much about your writing skills and how funny you are on camera, your acting skills. But I definitely think Instagram Live and doing any live shows at all, improv comes into play a lot, being funny on your toes and coming up with some of the funniest things to say right off after somebody said something, you know? And your timing. Timing is definitely a big deal when it comes to all that.
Sort of a newer avenue for you, I wanted to ask about your breaking into stand-up.
Yes.
How has the process of that been relative to your other output?
Uh, very hard. It’s not easy. I think back in the day when you got your Kevin Harts and your Dave Chappelles coming up, it was completely opposite. With them starting off on stage before getting any chance to be on a screen. Now, it’s completely reversed, where we get a chance to put ourself on our own screens in front of millions of people before we step on a stage in front of millions of people, you know? So, it’s very backwards.
But learning from tips from guys like Kevin Hart and meeting him and him just coaching me up, you know, giving me all type of different aspects on like how the live world is, and how important it is to have that, and how it can only help. So just people I’m motivated by that talk to me that have done this stuff before, just sitting down and having conversations with them, it helps. And it definitely motivates me even more to compete.
It’s a great moment for you when Drake hits you to be in the “Laugh Now Cry Later” video in 2020.
Yes.
What type of game did he impart to you, or has he imparted to you since then?
Man, that dude is the genius, man. Honestly. He has just taught me so much about the business and being just a genuine person and, you know, not listening to the people that tell you that the industry is this place where you gotta be fake and all that. He’s just one of those people. ‘Cause I’m a genuine person as well, and I think he picked that up as soon as we met. And our relationship has just been great ever since, you know? But he’s one of those people where he’s just taught me so much just about the business in general and, you know, how to move. And yeah, he’s … bro, that dude has mastered … [laugh], like, the art of everything, you know? And yeah, he’s just such an inspiration, and it’s great to have him as a friend.
The commercial work, that’s light work for you, I’d imagine, at this point, given all that you’re doing.
Yeah.
How’s that been for you?
Uh, the commercial work. Everything has just been so fun, man. Some of these commercials are so fun, especially when they give me free range to be myself and let me bring my writing team on. You know, I have a writing team under my company, 4Lifers. It’s a production company that we’re gonna shoot all my movies and TV shows under. And I bring a lot of my writing team on when I do skits and stuff, so they help me out with so much. And with their help, it’s amazing to have them during these commercials and stuff. But yeah … the commercials, honestly, bro, has just been a blessing, and it’s been such a new avenue for me to show off my comedic skills to the world even more.
You got an ownership stake in a team in the Fan Controlled Football League. What made that the move for you personally, professionally?
Honestly, I just like ownership, man. And I always loved football. I grew up playing football when I was younger, so when we were kinda presented the opportunity to have some equity in something, I was all for it, you know? ‘Cause, you know, getting hired for things, is only so much. At least tryna have a long career, you can get paid for stuff, but if you’re not owning anything and having anything equity-wise for the rainy days to come, there’s no point. And, you know, tryna have a long, lasting career. So yeah, that was the biggest play for me, and I loved it. We did the first year last year, and it was amazing, bro.
On the flip side of that, how do the influencer partnerships work out for you at this point, at the level of fame you’ve reached? Is that where the real money’s at as an income stream?
Give me an example of … like what?
So you got the hard seltzer.
With Happy Dad.
Yeah. Happy Dad. Things like that, is that a sense of stability, or how does that factor in?
Oh yeah, definitely. We bought into Happy Dad, a piece of the ownership of Happy Dad. And I had already studied the brand for so long. I think they had started last year. Me and Kyle started as friends, through Nelk. They also do funny like prank videos and stuff. We went on a couple of trips together. We had mutual fans, and I think it only felt right to do, you know, a equity play with them. So, yeah, the drink is amazing. I just loved everything about it, and I loved how many people enjoyed having the drink as well. So I was like, as long as me and my friends and my people, my family, everybody enjoyed it, I say, why not, you know? The product was good. The company’s even better. I think everything just lined up, the stars lined up, but definitely equity is a big, big play inside of that.
Elon Musk is tweeting about bringing back Vine. Did you mess with Vine? I know you started on IG, but what do you think about if that came back as a platform?
Hey man, I’m all for it. I don’t know too much about it [laugh], but I mean, it sounds cool if it does. Hopefully they, uh, lengthen the videos a little bit longer than six seconds.
Yeah [laugh]. The process of putting out material for you is platform-agnostic, right? Like you’re gonna be on anything that’ll, uh, feature video, I’d imagine.
Yes. … Yes.
This feature film that you’ve got coming up, working with Chloe Bailey and Quavo. What can you tell me about the feature you’ve got coming here?
Yeah, “Praise This” is a great movie, man. It’s a comedy. It’s down-to-earth. It’s a Black comedy. You know, we don’t really have too many Black comedies anymore that are like thriving and, you know, doing good, and a success. I think, honestly, bro, we just all put together some of the greatest people that are doing it right now, with the Chloe Baileys and the Quavos and the Will Packers and the Tina Gordons — you know, these are all people involved in the filming — and of course myself. But I think that movie’s gonna be a really good movie when it comes out, and I think it’s gonna hit the culture very hard. I don’t know if I could speak too much about what happens in the movie, but yeah.
4Lifers
What do you see from an acting standpoint for you down the road? Are we gonna see you on some Robin Williams type sh-t? Will you ever get into serious roles, or how do you see your acting future?
Um, I think we just gotta see what the future holds. I don’t know. We’ll just see. I think I was definitely inspired by Jamie Foxx and his role in “Ray.” I was also inspired by Will Smith and how he did Muhammad Ali. If there was a day where it comes, I’d do a biopic. I think I would do a serious biopic. Yeah, when that time presents itself, maybe a Heavy D. I always, grew up, everybody said I looked like Heavy D. [Laugh].
[Laugh].
Maybe that’ll be in the works, I play a Heavy D role.
They gotta make that happen.
Yeah, man. Nah. But, uh, yeah, I think a biopic definitely. I was just inspired so much by Jamie Foxx playing Ray and Will Smith playing Muhammad Ali.
What do you see in the future of social media generally, and your participation in it? How do you continue to evolve with it to keep people interested?
Yeah, I love that question. I think we’re only at the beginning, I think a lot of people slept on social media from jump. I remember a lot of people saying when some of the early people were blowing up and not getting paid so much, people were blowing up and everybody was like, “Oh, you get famous on there, you only famous on the internet. You ain’t getting no money for real.” And now some of these dudes like Mr. Beast are billionaires, you know what I’m saying? So it’s like, y’all can’t no longer say it don’t equivilate to real money, ’cause, hey, look at us know, you know I’m saying? So, yeah, it’s constantly evolving, and I think a lot of people gotta wake up and get in where you fit in. You can’t even have a business nowadays without having social media. Literally. Like, you can’t even own a shop or own anything without having social media. You gotta have social media for it to verify. People wanna see that online.
