Druski has established himself as a pioneer in shaping the future of comedy. His journey may have taken a different turn without the significant endorsement 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 transforming his life and validating his career after featuring him in his 2020 “Laugh Now Cry Later” music video.
“The pivotal moment for me was when Drake called for the ‘Laugh Now Cry Later’ music video. Everything changed from that point because brands began to take me seriously,” he explained. “Now it’s transactional with everything.”
Druski elaborated: “Once I was seen with Drake and Lil Durk, alongside Marshawn Lynch, Kevin Durant, and Odell Beckham Jr. in this video, my role as the comedic relief in ‘Laugh Now, Cry Later’ meant much more than just another music video.”
At that time, Drake was simply an admirer of Druski’s content, but he wasn’t earning much from it. The music video appearance changed everything, as Druski noted how brands started to view him in a “broader light” and his value increased. “They began to see me as an actual star, rather than just another comedian,” he added.
The OVO founder was an early supporter of Druski and recognized him as a leader in the new wave of comedy. “It’s incredible to hear this from someone I consider a megastar,” he said. “It changed everything almost instantly.”
Druski continually seeks new avenues to enhance his profile and comedy career; he became the first comedian to grace Billboard‘s No. 1s issue, hosted the 2026 BET Awards in June, received a Webby Special Achievement Award in 2026, toured arenas with Coulda Fest, and featured on Justin Bieber’s SWAG album in 2025.
The track “Laugh Now Cry Later” saw Drake collaborate with Lil Durk during the COVID-19 pandemic in August 2020, reaching No. 2 on the Billboard Hot 100 and garnering two Grammy nominations.
Druski has also appeared in other music videos such as Jack Harlow’s “Tyler Herro,” “Churchill Downs,” and Lil Yachty’s “Oprah’s Bank Account.”
Check out the full interview with Druski below. Discussion about Drake starts around one hour and eight minutes in.
