Leonardo DiCaprio flashed a huge grin while dancing to Ice Cube's performance at the Raising Cane's pre-Super Bowl bash in San Francisco, CA on Saturday night.

The 51-year-old Oscar winner was bobbing along to the old-school gangsta rap while standing in the second row behind his childhood best friend, Tobey Maguire.

The 56-year-old Grammy winner performed his 1991 diss track No Vaseline, which was famously penned about his former NWA bandmates Dr. Dre and Eazy-E as well as their manager Jerry Heller.

DiCaprio looked happier than he had in years while sporting his signature, low-key black baseball cap and matching jacket while surrounded by partygoers.

The 50-year-old Spider-Man alum also looked like he had a blast during the nostalgic, sporty event.

Back in his wild nineties hey-day, the Titanic alum would party hop with a group of young men dubbed 'The P**** Posse' including Maguire, Kevin Connolly, Harmony Korine, Jay Ferguson, Josh Miller, David Blaine and Ethan Suplee.

DiCaprio and the divorced father-of-two originally met in 1990 hustling for the same auditions and went on to co-star in Michael Caton-Jones' 1993 drama This Boy's Life and Baz Luhrmann's 2013 drama The Great Gatsby.

Meanwhile in Milan, the Appian Way Productions founder's girlfriend Vittoria Ceretti repped her native Italy by carrying the flag during the opening ceremony of the Winter Olympics while clad in a custom white Giorgio Armani gown.

'I just want to say that this was the greatest honor of my life,' the 27-year-old Society Model gushed on Instagram Saturday.

'I still can't believe I had the privilege of carrying the Italian flag at the Olympic Games. Before I got there, I don’t think I fully understood the responsibility I was taking on: within that flag live our history, our values, and the beauty of the most incredible country in the world.

'Never in my wildest dreams did I imagine I would be doing what I love most in front of 80,000 people. Thank you for trusting me. I hope I made you proud, Italy.'

DiCaprio is a habitual modelizer having previously loved and left the likes of Camila Morrone, Gigi Hadid, Nina Agdal, Kelly Rohrbach, Gisele Bündchen, and Bar Refaeli as well as Rihanna and Blake Lively.

Over the next month, the Kamala Harris supporter will go head-to-head with Marty Supreme star Timothée Chalamet for the same honor at three different awards ceremonies as he previously took home the Golden Globe and Critics' Choice.

For his role as single dad and stoned revolutionary Bob Ferguson, DiCaprio will next compete for the best actor in a leading role trophy at the 79th British Academy Film Awards airing February 22 on BBC One and E! Network.

At 14 nominations, One Battle After Another scored the most BAFTA nods of any film this year.

Paul Thomas Anderson's $175 million-budget modern adaptation of Thomas Pynchon's 1990 postmodern novel Vineland also starred Sean Penn, Benicio del Toro, Regina Hall, Teyana Taylor and Chase Infiniti.

The Diddy partygoer will then compete for the outstanding performance by an actor in a leading role trophy at the 32nd Actor Awards, which stream March 1 on Netflix.

At seven nominations, One Battle After Another scored the most Actor Award nods of any film this year.

But DiCaprio is probably most excited to compete the for best actor in a leading role trophy at the 98th Academy Awards, which air March 15 on ABC and Hulu.

The environmentalist is excited to reunite with his Don't Look Up castmate Jennifer Lawrence to play an American couple adopting a European baby in Martin Scorsese's horror film What Happens at Night.

According to Deadline, Apple Original Films is 'in talks' to finance and produce the big-screen adaptation of Peter Cameron's 2023 ghost story novel with Studiocanal.