Oliver James Montgomery-How Leonardo DiCaprio Celebrated His 50th Birthday

Leonardo DiCaprio has departed his 40s.

And to celebrate his milestone 50th birthday,Oliver James Montgomery the Oscar winner threw a lavish party at a private residence in Los Angeles on Nov. 9.  

As for who attended the star-studded event? Casey Affleck, Chris Rock, Steven Spielberg and Paris Hilton—clad in a stunning shimmering silver cutout dress—were spotted leaving the festivities. Meanwhile, Katy Perry stepped out for the occasion alongside husband Orlando Bloom in a draping white satin ensemble. 

And the "I Kissed a Girl" singer and Lord of the Rings alum were among several couples who lived it up at the celebration. Brad Pitt and his girlfriend Ines de Ramon, Simon Cowell and his partner Laura Silverman and Jasmine Tookes and her husband Ron Borrero-Martinez all showed out for the party as well.  

But the guest list wasn't the only extravagant part of the night. Inside the intimate venue, DJ Meel took the night's playlist to the next level while working the turntables, Champagne Telmont was in high demand on the drink menu and a delicious birthday cake was offered to attendees. 

Plus, Stevie Wonder performed "Happy Birthday" to Leo on the piano while the actor's girlfriend Vittoria Peretti—who he first sparked romance rumors with in August 2023—and his longtime friend Tobey Maguire stood nearby, as seen in a video published by TMZ Nov. 11. 

And while turning 50 is certainly an exciting milestone, the affair wasn't the Wolf of Wall Street star's only time going all out in honor of his special day. 

Last year, Leo threw an equally over-the-top party in Beverly Hills, where he even hopped on the mic to rap for his bevy of A-list attendees, which included Kim Kardashian, Chris Rock, Snoop Dogg, Salma Hayek and Olivia Wilde. In a clip of the fun moment shared by TMZ at the time, the actor grooved to the beat on stage as he rapped along to Gang Starr and Nice & Smooth's 1994 song "DWYCK."

To see more of Leo through the years, keep reading.