How Comedy King Druski Is Helping Music’s Biggest Stars Own the Internet

In early July, as he put the finishing touches on what would become one of 2025’s biggest albums, Justin Bieber had a question for the new collaborator in the studio with him. “Why wouldn’t you be my therapist?” Bieber asked Druski as they finalized a trio of skits that would punctuate SWAG, which arrived days later.

The R&B-forward set marked a mature, fresh chapter for Bieber, and he knew the comedian’s sprawling reach and range made him a perfect partner to help usher in that transition. “He wanted a way to address everything different outlets and the public wanted answers about, and I think he wanted to do it in a comedic way,” Druski says. “He played the album for us and then we had conversations between each song. It was all one take, just talking to him about what’s been going on in his life.”

From Dunkin’ Super Bowl commercials to Bieber album cameos, Druski defined 2025 like no other star — and pop culture’s biggest names are taking notice.

Comedian and social superstar Druski will host the Billboard 2025 No. 1s Livestream on Tuesday, Dec. 9, starting at noon ET/9 a.m. PT, where he’ll welcome special guests to help reveal the biggest chart-toppers of 2025. Watch here.

Since he broke through with his sketch comedy on Instagram in 2017, the 31-year-old multihyphenate has constructed one of the most innovative cultural brands of the last decade. But while the medium-traversing mogul’s trajectory has created a new blueprint for aspiring entertainers, from his early skits to his current Coulda Been web series and label Coulda Been Records, Druski has drawn on an older, tried-and-true playbook: that of iconic comics like Cedric the Entertainer and Dave Chappelle.

“My mom used to record me entertaining the family,” recalls Druski, who was born Drew Desbordes and raised in Georgia’s Gwinnett County, outside of Atlanta. “As young as 5 years old, I’m on video in character doing silly s–t to make my family and friends laugh.”

Growing up, Druski spent his childhood sneaking downstairs to catch glimpses of Chappelle’s crass Comedy Central skits — and he also enjoyed Cedric the Entertainer’s family-­friendly style with his mother. “As a kid, you don’t have control over the remote, so I would watch what they watched,” he says on a mid-November afternoon in a Philadelphia hotel room, ahead of his performance there that night as part of his arena-headlining Coulda Fest Tour. As a teenager, like much of the world, Druski fell under Kevin Hart’s spell. “That was a big moment when Kevin came into the culture,” he explains. “Being able to work with him now is like talking to one of your heroes.”

Chappelle’s edge, Cedric’s affability and Hart’s hip-hop bona fides are all present in Druski’s comedy, but his keen observations tie it all together; the comments for practically every skit he posts hail him as a “cultural anthropologist.” Druski’s superpower is his idiosyncratic ability to emulate the most minute details of niche characters, from the empty-­headed glee behind his Woulja character’s underbite to the satirically glib Coulda Been Records CEO he plays.

“Druski reminds me a lot of what Eddie Murphy, Martin Lawrence, Jim Carrey and Mike Myers were: performers who could take on different characters and create whole franchisable enterprises around them,” says Emmy Award-nominated film/TV producer Kenya Barris, who’s attached to one of Druski’s upcoming film projects, The Diggers. “He’s giving a new audience an appreciation for the time and effort it takes to entertain beyond normal-life antics. He also knows what he doesn’t know, which is one of the most powerful things. That makes him dangerous.”

Through his late-2010s skits, which launched his beloved Kyle Rogger frat bro character, Druski grew into a social media powerhouse. He caught the eye of hip-hop A-listers like Drake, Lil Yachty and Jack Harlow, who all cast him in music videos in 2020 (“Laugh Now, Cry Later,” “Oprah’s Bank Account” and “Tyler Herro,” respectively), moved by both his comedic chops and his tens of millions of followers. By fall 2021, he was opening for J. Cole and 21 Savage’s The Off-Season tour; the following year, he supported Chris Brown and Lil Baby’s joint One of Them Ones Tour.

Druski also struck gold with the parody label Coulda Been Records, which stemmed from his pandemic-era Instagram Live sessions and helped him become more than hip-hop’s favorite sidekick of the moment. Initially, the endeavor started as a way for Druski to give talent he scouted their big break, even if that meant being in on his hysterical bits. But a massive influx of hopeful participants demanded a stronger framework. “I wanted to make it look like American Idol, so we put all the money I got from brands into making Coulda Been Auditions,” Druski explains of the YouTube series he launched as part of the project. “We’ve had so many different stars from the auditions.”

Several Coulda Been Auditions stars appeared on Coulda Been House, a reality competition-inspired YouTube series Druski premiered in 2024, including season one winner Ugliest Rapper Alive and season two victor Hon3y Bandz. Both artists are signed to Coulda Been Records, which Druski formalized as a corporate entity in 2022, but neither has released any music. Operating independently, Coulda Been Records has released five singles over the past two years, including Coulda Been House season one theme song “Standin’ on Bihness” (with Snoop Dogg and DJ Drama) and season two theme “Come to Coulda Been” (with Lil Yachty and BYNX). “It’s not time yet, but I definitely will put out a Coulda Been album,” he says.

Streaming platforms like Netflix and Hulu passed on Druski’s short-form show concepts, including Coulda Been Auditions, so he started producing everything in-house through his 4Lifers entertainment company and debuted the shows on YouTube, where they continue to live.

“From there, I wanted to bring it to a live setting, so we did the Coulda Shoulda Woulda Tour,” he says. “It wasn’t the best tour — it was in theaters — but it was a learning situation. Now we’re on this arena tour, and we’re able to bring characters and spoof things Morgan Wallen and Usher do on their tours. I’m able to play the piano, hold live auditions and bring special guests. I put everything from all my worlds into this tour. The biggest thing is being able to accept a hybrid show, not knowing what to expect and still coming out with a great experience.”

The latest season of Coulda Been Auditions, which features appearances by Mark Wahlberg, Sexyy Red and Fuerza Regida, earned nearly 60 million views across its first eight episodes, and there’s a New York-set, Timothée Chalamet-assisted episode on the way in December. Meanwhile, the new seasons of its sister shows — Coulda Been House, which pulls from reality TV competitions, and Coulda Been Love, which riffs on dating programs — both posted tens of millions of views on YouTube. Druski thrives on fashioning social media stars out of society’s most lovably delusional characters, and the Coulda Been franchise has minted a slate of social media stars; chief among them is Bambi, his “baby mama” (yet another Druski bit) whom audiences go wild for when she graces the Coulda Fest Tour stage. Coulda Been grew in tandem with Druski’s overall stardom, which helped him land a slew of major brand partnerships: NBA, Bud Light, Meta, Amazon, Google Pixel, Pepsi, American Express, EA Sports, even Spotify.

In 2024, Druski started officially releasing music of his own through Coulda Been, including collaborations with Lil Yachty & BYNX (“Come to Coulda Been”) and Yung Bleu & Young M.A. (“Coulda Been Love”), earning over 2.1 million official on-demand global streams as a stand-alone artist, according to Luminate. But SWAG, Bieber’s surprise seventh studio album, marked the biggest musical moment of Druski’s career, and it further upped his cultural cachet. Upon its July release, SWAG hit No. 2 on the Billboard 200 and launched a pair of Billboard Hot 100 top 10 hits alongside three skits featuring Druski assuming the role of The Biebs’ therapist. Through Nov. 20, those three interludes had collectively garnered 78.7 million official on-demand global streams, which Billboard estimates generated $415,000 in revenue.

That crossover moment on the now Grammy-­nominated album cemented Druski as the defining comedian of his generation, someone who transcends mediums as easily as he does demographics. During a pass-the-mic segment at his Nov. 14 Philly show — which he opened by playing piano (he has been classically trained since middle school) and belting a song referencing Sean “Diddy” Combs’ notorious baby oil allegations — a middle-aged white woman revealed that her family calls their newborn “Mooski” after the comedian. At that same show, Druski parodied Morgan Wallen’s I’m the Problem tour walkouts, staged a search for Philly’s top “studs” (read: Black masc-­presenting lesbians) and brought out guests from Soulja Boy to JT of City Girls. With Coulda Fest, Druski has headlined arenas on both sides of the pond, including an Oct. 11 Barclays Center show in Brooklyn that grossed $372,000 from 7,351 tickets sold, according to Billboard Boxscore. Seemingly everyone loves Druski — even those who aren’t one of his nearly 30 million social media followers — which possibly helps to explain how he pulled off a whiteface skit in 2025 without igniting a digital race war.

“When will teachers and professors start to use creators like Druski as case studies in media, communication and film classes?” wonders Hart, who won a Streamer Award alongside Druski and Kai Cenat last year. “He is paving the way for so many future stars, and he’s captured the voice of his generation. Druski has learned how to use data and metrics to keep his audience engaged and entertained the same way comedians before him learned how to move on from a joke that may not hit.”

Druski is closing his banner year hosting Billboard’s first year-end Hot 100 countdown livestream, but his eyes are already set on 2026. In addition to producing new seasons of his three Coulda Been shows — all of which he invests “millions” of his own money into — Druski is prepping two films and a TV series. A24 has expressed interest in The Diggers, a team-up with comedians Shane Gillis and Theo Von based on a spoof trailer the comics posted in June; the horror-comedy Livestream From Hell, which will also star Hart and Cenat, is in production by Hart’s Hartbeat with David Janoff attached to write; and Netflix recently greenlit a series based on Druski’s viral airport skits.

“I love Timothée Chalamet. I love Zendaya. But it’s got to be more, particularly from a comedy standpoint,” Barris says, stressing how many next-gen acting stars skew toward drama. “When’s the last time we could point to a big comedic star? Not a comedian, but a comedic star. It’s such a wide-open lane, and I think Druski wants it — and he’s in a place to grab it.”

How did you get on the Justin Bieber album?

Grammy-nominated! It’s crazy even thinking about it. I feel really good about [SWAG] winning [album of the year], too. I’ve been friends with Bieber for three or four years, just not publicly. He’s always reached out to me through text, like, “Yo, if you’re in L.A., let’s go golf!”

One day [in July], he asked me if I was in L.A., and I happened to be at the airport. We were getting dropped off at the gate in the Uber and Bieber’s like, “If you’re still here, I need you to come to the studio right now. I’m turning in my album tomorrow.” I’m like, “What does that mean?” And he’s like, “Yo, I want you on the album. You just have to hurry up and get here.” So I canceled the flight, got back in the Uber, and we drove to the studio. We stayed there the entire night and had a bunch of random conversations he recorded.

Who else would you want to do skits for?

After JB, how do you outdo that? I think I’m cool with this moment. Especially if [SWAG] wins this Grammy. I don’t want to touch too many albums now. Being able to do what DeRay Davis did on Kanye West’s [The College Dropout] was a moment. I would listen to that as a kid, and [SWAG] allowed me to get my comedic chops off on an album heard by a lot of people.

What collaboration could you do that would blow your parents’ minds?

James Brown. (Laughs.) And if it ain’t James Brown, they don’t give a f–k! Maybe Stevie Wonder.

How do you recruit artists for your tours and skits?

Everybody we have on the tour right now, I’ve either had a great relationship with or we’ve done some kind of content together. Soulja Boy was a good friend, and I was super inspired by his whole come-up from when I was a kid, so I wanted his nostalgic feel on this tour. With Young M.A., I can’t not have a stud on the tour performing music! (Laughs.) And then [BigXthaPlug], when they say “the biggest, the largest,” they mean that.

I’m big on balance. We have Caleb [Pressley], who hosts Coulda Been Love, on the comedy side, too. Navv Greene, who’s a disciplinarian on Coulda Been House, helps me with all of my live comedy. Everybody on the tour is a part of something in the Druski universe.

Was Kevin Hart one of the first established comedians to reach out to you in a mentorship capacity?

Kevin is definitely the first established comedian who ever embraced me. You don’t really see too many comedians cliquing up and being all buddy-buddy with each other, so I didn’t expect that. You have to get it out the mud. Once you do, they have more respect for you. It’s no handouts in comedy.

I got invited to Michael Rubin’s all-white party, but [Kevin and I] didn’t get a chance to really chop it up. [A few months later], when we met in Atlanta backstage at his show, we had a one-hour talk about everything. What to do, how to align yourself in this business, how to separate yourself from others who are also doing it, what real hard work looks like, etc.

Which parts of his advice stuck with you the most?

He was using all types of [analogies] and f–king big words. (Laughs.) It’s like when your dad tells you those sayings. He told us something like, “You don’t want to be on the roller coaster and then get to the top.” I don’t know what the f–k he meant, but he was saying that you don’t want to be enjoying the ride so much that you don’t realize when it’s going down. I know it had something to do with staying consistent and not getting lost in the moment.

What have you learned from observing others who attempted to transition from social media to traditional comedy?

When you’re in the public eye and you go through ups and downs, a lot of people get down on themselves and quit. Or some people get success and then they get stagnant and comfortable. I haven’t yet gotten that “All right, I’m here” feeling. I study people from the past who have made mistakes in the same lane I’m in. I pay attention to the reason why they fell off.

I try to step outside the box of people telling me, “You’re just a social media person” or “You’re not an entertainer, you’re a comedian” or “You’re not a comedian because you don’t do standup.” I try to do things people may not see coming, or I try not to stay on the same thing. Other comedians may have something great going, and then they milk it till it’s not funny anymore. I noticed that from a lot of people who came up through social media, and I never wanted to do that. To survive in this business, you watch what the greats have done, and none of them have stayed on one thing. They evolve.

What will confirm that Druski is finally “here”?

An Oscar. Or the Mark Twain Prize. That can happen whenever; I’m very patient. I haven’t gotten to the point where I’m like, “I’m that guy.” I know there’s so much more to come.

Deciding not to live in L.A. was an important part of maintaining your artistry, right?

I moved there for about six months [in 2023], and I noticed I was losing myself. We were going to parties and different events for big companies, and I wasn’t as inspired as I used to be. With comedy, you have to be around the real. And if you’re not around that, you tend to lose the art. It’s hard to be tapped in and know what’s funny or where to go with your content when you’re not around the real stuff. I write with my crew, and we all agreed we weren’t as on point as we once were. We had to get back [to the culture]. Maybe it wasn’t the right time for me to move there; maybe it’s for when I have a family and kids. Maybe I have to do some movies first. Right now, the best place for me to be is in Atlanta; there’s so much stuff going on culturally. And there’s so many fake people in L.A. Everybody’s artificial … and I just couldn’t do it.

What can audiences expect from Livestream From Hell with Kevin and Kai Cenat?

These are the heavy hitters. The three of us coming together was undeniable because everybody pulls their own weight. When Kai had us on the stream for the very first time, we instantly knew this trio was going to work. We got an award for that stream! I honestly get mad when we link up and there’s no cameras because it’s so much funny s–t the world misses. The world is going to know this trio forever. We’ve already shot the movie, so we’re just tweaking small things now.

What has Kai taught you about the streaming landscape?

Streamers don’t f–king sleep. And when they sleep, they still on stream! (Laughs.) You have to be disciplined. A lot of people see what Kai does and think they’ll get rich just talking into a camera. Kai’s not f–king around. He’s fully locked in 24/7 and he has set dates for shoots, teasers and trailers. He’s really applying pressure in that space, and it’s impressive as f–k watching it behind the scenes.

Which comedic actors do you look to?

Chris Farley, Will Ferrell, Chris Tucker, Eddie Murphy; classic character work. When Jamie Foxx did Ray and Django Unchained, seeing comedians do [dramatic roles] was really inspiring. Those are the people who truly inspire me and where I want my career to go.

What are the top three musical moments of your career so far?

Recording the theme song for Coulda Been Love was a big moment because it felt like [The] Fresh Prince [of Bel-Air]. Definitely the Justin Bieber album. And one shift in my career I always refer to is Drake having me in his “Laugh Now, Cry Later” music video. During that time, a lot of people didn’t respect me, and once Drake took a chance on me, a lot more brands like Nike and Google followed suit. Drake saw the vision.

Outside of Drake, which artist co-sign meant the most?

Leonardo DiCaprio. And he knew everything Druski. Everything. He knew about Coulda Been Records, he was a big fan of my character work, and he told me, “Man, you are really amazing.” He had a deep, 30-minute talk with me when I ran into him at an event last year. I was in shock, just taking in what he was saying and asking questions. The whole thing was stunning.

Have you gotten a chance to work with Morgan Wallen yet?

We’re working on a country Coulda Been Auditions [episode]. We’re really good friends, so hopefully he’ll find some time to do this in Nashville.

If you ever bring back that whiteface skit, Morgan has to make a cameo.

(Extended laugh.) That was a moment! I always knew that skit would have that kind of reach. A lot of people have tried to re-create it. It wasn’t until I saw it on the news and my family kept calling me that I realized how much it blew up. It was on multiple news channels: “Comedian does whiteface,” and it really was never any backlash. Everybody loved it. We’ve gotten to the point where my s–t is making it to the news when I put it up!

What do you think makes a star in 2025?

You have to be very confident and consistent. There’s no days off for any of this s–t at all. Even if I am chilling, it’s hard for me to relax because I’m constantly thinking about what I could be doing. How can I outdo the guy who’s somewhere in the world trying to outdo me? I pride myself on being very disciplined. People may think I’m silly and they may wish they could have my life, but I don’t know if y’all can handle these shoes. I know it’s comedy, but a lot of hard work goes into this.

This story appears in the Dec. 13, 2025, issue of Billboard.