Druski has built an entertainment empire from making people laugh, but he says one call from Drake helped turn his growing internet popularity into something the business world could no longer overlook.
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During a September 24 conversation with Steven Bartlett on “The Diary Of A CEO,” Druski reflected on the years before major brand deals, television appearances, and large-scale productions became part of his career. When Bartlett asked about the moment that changed things financially and professionally, the comedian pointed directly to Drake recruiting him for the “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,” Druski said.
He explained that the opportunity immediately changed how companies approached him.
“Everything shifted after that because brands started to take me seriously. It wasn’t no more sending free merch and, ‘Oh, you get this’ or we’ll bring you out to this event, and we just want your appearance, and you could get in free. Now it’s transactional with everything.”
That shift was significant because Druski was not simply appearing beside another rising artist. Drake released “Laugh Now Cry Later,” featuring Lil Durk, on August 14, 2020. The Dave Meyers-directed visual was filmed at Nike’s headquarters in Oregon and included appearances from Kevin Durant, Odell Beckham Jr., Marshawn Lynch, and Druski, who was still widely known online as Druski2Funny at the time.
Druski said being placed in that company gave his comedy a different level of visibility.
“This meant a lot more than just another music video,” he explained.
The Drake and Druski relationship had already started privately before cameras ever rolled. Druski told Bartlett that Drake had been watching his comedy online and communicating with him through direct messages. Their exchanges were initially brief, usually involving Drake reacting to videos he thought were funny.
“He was a big fan of a lot of the stuff I was posting during that early time, but it wasn’t until then, no real money was coming in. No money at all.”
Druski said their conversations became more serious once Drake told him he would be featured in the video.
“It was very just short back and forth, laughing at this video, laugh at that video, find this funny, find that funny, and then we had like a long conversation once he told me that I would be starring in that music video and that was just about like leading this generation of comedy.”
Hearing that level of praise from Drake was difficult for Druski to process while he was still trying to establish himself.
The moment fits into a much larger story Druski shared throughout the nearly two-hour interview. He discussed leaving college to pursue comedy, having his car repossessed, surviving an armed robbery, and continuing to create while barely earning money from his growing online audience. He also spoke about eventually investing in his own ideas after companies including Netflix, Amazon and FX passed on projects he pitched.
Years later, his career is operating on an entirely different scale. A recent GQ profile of Druski detailed his expansion from social media comedy into television, film and independent production, including hosting the 2026 BET Awards and developing projects through his own creative operation. GQ also noted that Drake was among the earliest major celebrities to publicly support his comedy.
The Drake and Druski connection has continued well beyond a single video, but Druski still views that first major opportunity as something he cannot easily repay.
“That’s one of those things that’s just like, could never repay him, man.”
Looking at his early material now, Druski acknowledged just how much his work has evolved.
According to Druski, that shift did not take years to reveal itself. It happened almost immediately.
“It shifted everything almost immediately.”
What Drake gave Druski in 2020 was bigger than screen time. In Druski’s telling, the appearance helped change the conversation around his value, moving him from a funny creator receiving free products and invitations into an entertainer businesses were prepared to pay.
