Druski has proven to be a trailblazer in paving the way for the next generation of comedians. It all may have never played out the same for Druski if it wasn’t for a massive cosign from Drake.
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During an appearance on The Diary of a CEO on Thursday (Sept. 24), the sketch comedian credited Drake with changing his life and legitimizing his career after casting him in his 2020 “Laugh Now Cry Later” music video.
“The thing that changed my life at the time was Drake calling for the ‘Laugh Now Cry Later’ music video. Everything shifted after that because brands started to take me seriously,” he explained. “Now it’s transactional with everything.”
Druski continued: “Once I was seen with Drake, Lil Durk, we had Marshawn Lynch, Kevin Durant, Odell Beckham Jr. all in this video alongside me. Me being the comedic relief in this video, which was called ‘Laugh Now, Cry Later,’ this meant a lot more than another music video.”
Drake was just a fan of Druski’s content at the time, but he wasn’t making much money from it. That all changed with the music video appearance, as Druski detailed how brands began to see him in a “broader light” and the price started to go up. “They started to see me as an actual star, instead of just another amongst all these other guys who are doing comedian things,” he added.
The OVO boss was an early believer in Druski and saw him as the leader in the next generation of comedy. “This is wild to hear from somebody who, in my eyes, is a megastar,” he said. “It shifted everything almost immediately.”
Druski is always finding new ways to elevate his profile and comedy career, as he became the first comedian to cover Billboard‘s No. 1s issue, hosted the 2026 BET Awards in June, won a 2026 Webby Special Achievement Award, toured arenas with Coulda Fest and appeared on Justin Bieber’s SWAG album in 2025.
“Laugh Now Cry Later” saw Drake join forces with Lil Durk during the COVID-19 pandemic in August 2020, which peaked at No. 2 on the Billboard Hot 100 and picked up a pair of Grammy nominations.
Druski has made appearances in other music videos like Jack Harlow’s “Tyler Herro,” “Churchill Downs” and Lil Yachty’s “Oprah’s Bank Account.”
Watch the full interview with Druski below. Talk about Drake takes place about an hour and eight minutes in.
