Watch Leonardo DiCaprio Rap Gang Starr's "DWYCK" at 49th Birthday Party

The Oscar-winner has always been a massive hip-hop head.

Stephane Cardinale / Corbis via Getty Images / Via

Killers of the Flower Moon star Leonardo DiCaprio had a wild time for his 49th birthday. During a private celebration held for the Oscar-winner, DiCaprio sang along to numerous old-school rap classics, including Gang Starr's hit "DWYCK," featuring Nice & Smooth. The song appeared on the rap group's fourth album, 1994's Hard to Earn.

View this video on YouTube

TMZ (YouTube) / Via

Some social media users found the moment to be "cringe," but DiCaprio has long been a hip-hop enthusiast. He's partied with 2 Chainz, lauded Jay-Z for executive-producing 2013's The Great Gatsby soundtrack, and he's close friends with Q-Tip, even attending A Tribe Called Quest concerts in the 1990s to support the rapper and iconic beatmaker.

In his 2021 memoir From Staircase to Stage, Raekwon shared that DiCaprio was interested in being a part of a Wu-Tang Clan biopic, which RZA shut down due to being in talks for a multi-season series. The project eventually became Wu-Tang: An American Saga, which lasted for three seasons on Hulu from 2019 to 2023.

“He talked about his production company and all the directors he thought might do a great job—and these were big names and people he’d worked with," Raekwon recalled about meeting with DiCaprio in Brooklyn. "He was super open to the idea, and after that meal, he had his production company executives reach out to me.”

Raekwon added that RZA met with DiCaprio's team, and although he saw the actor “playing a role," it would never come to fruition.

“I could tell [RZA] wasn’t going to agree to do it, and my instincts told me why: My guess is that he was already in bed with a production company, deep into developing the scripted series for TV, even though none of us had signed off on it," Raekwon said.

Latest in Pop Culture