Watch Leonardo DiCaprio and Tom Brady party together at Wayne Boich’s star-studded Art Basel Miami bash



Leonardo DiCaprio and Tom Brady were flocked by a bounty of beauties at Wayne and Cynthia Boich’s ridiculously star-studded private mansion party celebrating Art Basel Miami on Friday night.

“Leo and Tom were letting loose at a back table at the party,” a partygoer tells Page Six of Boich’s exclusive waterfront fête where Snoop Dogg and Lil Wayne performed.

“They were both dancing to the music and all these beautiful women were surrounding Tom.”

Another source added that the former NFL star looked like he was “on the hunt” for a lady and the “Killers of the Flower Moon” actor was “basically a wingman” for the retired quarterback.

“They didn’t have to lift a finger,” the second source added, explaining that women were bee-lining for their packed table all night.

Tom Brady and Leonardo DiCaprio hit Wayne and Cynthia Boich’s exclusive mansion party celebrating Art Basel Miami on Friday night. Leah Bitsky/Page Six
“Leo and Tom were letting loose at a back table at the party,” a source tells Page Six. Page Six
Brady and DiCaprio were both flocked by models. Page Six

And a little rain didn’t stop Brady, 46, and the Hollywood star, 49, from keeping the night going.

“All of a sudden, it started raining and Leo and Tom stayed at their table and just looked like they were having an amazing time while other guests sought shelter inside Wayne’s house,” the partygoer said.

At one point, Brady was seen laughing and smiling while DiCaprio, wearing his signature black baseball hat, closely chatted in a corner with Sean Penn.

The actor was seen chatting with Sean Penn. Page Six
DiCaprio wore his signature black baseball cap. Page Six
The retired NFL star was dressed casually in a black zip-up. Page Six

We’re told DiCaprio, who usually keeps a low profile, was a “total social butterfly” and was seen flitting around the party to schmooze with other celebrities and attendees.

“Leo looked like he was having the best time ever,” a spy tells us.

DiCaprio and Brady both stayed at the party until well after midnight before making their exit.

Meanwhile, Snoop, 52, was seen decompressing with a smoke session at the back of the party after performing for nearly an hour for the intimate crowd. He belted out several of his hits, including “Gin and Juice,” “Drop It Like It’s Hot” and “Young, Wild & Free.”

Lil Wayne performed some of his biggest hits. Page Six

Lil Wayne, 41, then took to the stage and rapped an impressive set featuring songs “Lollipop,” “A Milli” and “6 Foot 7 Foot.”

Other stars spotted at the A-list soirée included Dwyane Wade, Venus and Serena Williams, Cindy Crawford and husband Rande Gerber, Corey Gamble, Tyga, Jimmy Butler, Victor Cruz, Lindsey Vonn and boyfriend Diego Osorio, AE Edwards, Harvey Spevak, Noah Tepperberg and wife Melissa Wood and Google co-founder Sergey Brin.

As Page Six reported on Friday, Brady is “dating around” and keeping his options open after his short-lived fling with Irina Shayk.

Snoop Dogg was seen taking a smoke break after performing. Page Six

Brady and Shayk, 37, both attended DiCaprio’s Re:Wild event at the Superblue Museum on Thursday night.

“Brady was at the party briefly and he said hi to her, but he also said hi to a lot of other people,” a spy said.

The duo sparked dating rumors in May but things fizzled after less than four months together due to conflicting schedules. The former quarterback’s short chapter with the supermodel was his first public relationship following his October 2022 divorce from Gisele Bündchen.

A source told Page Six that Brady is dating around. Getty Images for Best Buddies
He had a short fling with Irina Shayk but things recently cooled off for the pair. irina shayk / Instagram
The former quarterback and Shayk both attended DiCaprio’s private party on Thursday. irina shayk / Instagram

Brady and the former Victoria’s Secret model, who were married for 13 years, share two kids: Vivian, 11, and Benjamin, 13. The athlete also shares son Jack, 16, with ex Bridget Moynahan.

Meanwhile, DiCaprio is seemingly off the market now that he’s getting serious with Vittoria Ceretti.

He and the Italian model, 25, have been romantically linked since they were seen making out on the dancefloor in Ibiza, Spain, in August.

DiCaprio is currently dating Vittoria Ceretti. Getty Images for Re:Wild
The Italian model has been linked to DiCaprio since the summer. Vittoria Ceretti / Instagram

“They’ve been spending quite a bit of time together over the past few months, and they’re enjoying getting to know one another on a deeper level,” an insider told Page Six in September while confirming their relationship.


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Ceretti has already met DiCaprio’s mom and the “Titanic” alum was seen spending Thanksgiving with her family in London last month.

DiCaprio spent time with Ceretti’s family last month. Getty Images for Balenciaga

The Oscar-winner, who was seen eyeing art pieces at the convention center earlier this week, most recently dated Gigi Hadid following his August 2022 breakup with his girlfriend of four years, Camila Morrone. 

Interestingly, Hadid, 28, has recently sparked dating rumors with Shayk’s ex-partner, Bradley Cooper.

Shayk and the “Maestro” actor, 48, were together for four years before splitting in June 2019 and continue to co-parent their 6-year-old daughter, Lea De Seine.



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