Before Drew Desbordes was appearing in Drake's music videos or living with NFL star Odell Beckham Jr., his mother scolded him with tears in her eyes beside the living room couch he'd flipped over as a stage prop.
Back then, he wasn't the comedian named Dolsky known to millions. He was a struggling college dropout recording goofy, aimless skits in his parents' house with the impossible hopes of becoming a social media star.
Along with the overturned furniture, Dolski's clothes were scattered among the boxes, and his mother scolded her son for leaving the school without a clear plan.
“It was horrible,” Dolski said. “It was horrible. She had had enough.”
In an age where there are seemingly limitless personalities on the internet, becoming famous takes determination, strategy and a little bit of luck. Mr. Dolski said his mother's criticism motivated him to pursue more mainstream success. He wrote down goals, one of which was to hone his voice as a comedian.
Mr. Dolski eventually found his breakthrough with his bawdy, anthropological humor videos, in which his popular characters — an overbearing sorority boy, an irate airport security guard and an adulterous warehouse worker — garnered millions of followers on Instagram and TikTok.
As people scrolling through their phones began to take notice, celebrities started to take notice, too: Professional athletes recited his sketches, Snoop Dogg wrote a song with him, and Google and Nike hired him as an anchor for their ads.
“The whole new realm of entertainment is on social media. He's authentic and knows how to embrace today's culture in a funny way,” influencer Jake Paul said.
Now, at 29, Dolski is looking to be seen as more than just the fun sidekick to the rich and famous — and he plans to use his newfound fame to pursue loftier ambitions, like leading roles in feature films, while also staying connected to his followers through badly filmed skits on his phone.
“This is about being able to transition and do bigger things, but the fans still want to see that guts, that funny, raw material,” Dolski said. “That's what drives the dream.”
Last year, Dulski headlined a comedy tour and opened for rappers J. Cole and Lil Baby. This year, he created and hosted a YouTube reality show, “Coulda Been House,” produced by his company, Four Rifles Entertainment. He is finalizing the announcement for Coulda Fest, a music and comedy festival to be held in Atlanta this year.
Dolski said the projects are an attempt to diversify his career.
“Nobody in this business ever falls behind, they just don't grow from their past successes,” Mr. Dolski said in his office, wearing a black collared shirt, camouflage hat and sandals. A friend once joked that he dressed like a fisherman. “You get bored of looking at the same thing over and over again.”
But Dolsky said he is aware of the potential for missteps as his presence grows, and that his work will face greater scrutiny because of his business ties.
“It definitely makes you rethink things,” he said.
The comedy industry is exploring what boundaries it can tolerate when it comes to sensitive or controversial content. In 2022, Dolski removed from social media a skit in which his character forced a woman to drink alcohol and then had sex with her without her sober consent.
“Sometimes you have to spice up your jokes,” Dolski said, adding, “You don't want to be that person who always stays in their shell. People love you for who you are, so just be yourself.”
The second son of a Catholic family, Mr. Dolsky grew up in Gwinnett County, Georgia, taking piano and karate lessons and his mother lathering his mouth with soap to punish him for the foul language that is now a staple of his videos.
“I don't agree with the language or the attitude,” his mother, Cheryl DeBold, a public health worker, said of her son's skit. “I wouldn't do it, but it's his life. At the end of the day, I just need to know that he's a good person at heart.”
She continued, “Drew is fully set up for success. No matter what happens, he knows the difference between right and wrong.”
Mr. Dolski studied broadcast journalism at Georgia Southern University but soon dropped out and took unsatisfying jobs in restaurants and warehouses, and made unfocused, crudely produced video clips at home.
That began to change after his mother's admonition. He adjusted his approach and started paying attention to social media trends. Some of his videos garnered attention, including one in 2018 in which he parodied an angry high school football coach's speech in the locker room at halftime.
“His most valuable skill is being able to take real situations that everyone experiences and put his own unique twist on them,” said Chukwuma Head Williams, Dolski's road manager and longtime friend.
One day, Dolski messaged rapper Jack Harlow out of the blue on social media to say he was a fan, and Harlow returned the compliment. The two met in Harlow's unfurnished Atlanta apartment shortly after, while riding on a bus during the rapper's 2019 tour. Dolski spent that Thanksgiving with Harlow's family, and made fun of the experience.
“Looking back, it was one of the best times of my life,” Harlow, a six-time Grammy nominee, said in an email. “We shared the same language and understanding, and I miss my dog every day we weren't together.”
Dolsky's fanbase has grown at an accelerated pace during the coronavirus pandemic. Drawing inspiration from “Making the Band” and “American Idol,” he grilled his followers on their singing abilities during Instagram Live sessions in a series called “Coulda Been Records.” Internet-savvy Drake noticed Dolsky's videos and invited the comedian to appear in his music video for “Laugh Now, Cry Later” alongside Beckham and NBA star Kevin Durant.
The song's title is now tattooed on Dolsky's right calf.
“I was like, 'Hey, I'm going to accomplish everything I can accomplish,'” Dolski said.
As pandemic restrictions eased, Dolsky became a regular at events like the Super Bowl and the NBA All-Star Game. He's worked as a spokesman for companies like Bud Light and Beats by Dre, and is perhaps best known for his commercials for the Google Pixel and the NBA. In spots, he often appears alongside Giannis Antetokounmpo and Jimmy Butler.
“He was really good at what he did and understood the role and impact he could have as a central figure,” said Daryl Butler, Google's vice president of Devices and Services Marketing. “He understood our mission.”
Though his successes are documented on the walls of his plush, marble-accented Atlanta home and autographed jerseys from NFL stars Lamar Jackson and Jalen Ramsey hang in the basement, Dolski said he doesn't feel completely successful yet.
He said major streaming platforms refused to air “Could Been House,” an adaptation of his Instagram sessions, and FX canceled a show he and Kevin Hart were scheduled to star in because of the Hollywood strike. Dolsky had a supporting role in the film “Praise This,” which was released on the streaming service Peacock, but has yet to land a major theatrical film role despite two years of auditions.
“That's part of the job,” he said. “The no's lead to the yes's.”
