LEO SEASON

Inside Leonardo DiCaprio’s Insane Saint-Tropez Gala with Madonna and Kate Winslet

The famously photo-shy actor even took selfies with Lenny Kravitz.


The Leonardo DiCaprio Foundation 4th Annual Saint-Tropez Gala - Dinner & Auction
Anthony Ghnassia/Getty Images

Once a year, Leonardo DiCaprio performs his annual ceremony of removing his newsboy cap and putting his absolutely-no-photos-ever policy on hold to throw his annual gala for his eponymous Leonardo DiCaprio Foundation, where he obligingly poses for photos with everyone from Madonna to Sean Penn—all, of course, in the name of the environment.

This year’s edition, the group’s fourth, was held in Saint-Tropez—somewhat of an unlikely locale for an environmental group, given the outsized carbon footprints of private jets. But after Leo took one for the team and decided to fly commercial, everything seemed to be smooth sailing for the droves that made it to the coastal town on Wednesday night. In part thanks to commissioned works by artists like Damien Hirst and Richard Prince, the evening, which included a pescetarian dinner that reportedly featured “Tropezienne eggs” and mushroom waffles, raised tens of millions of dollars toward saving the earth, whose demise—thanks in part to President Trump’s withdrawal from the Paris Climate Accord—seems to be coming much sooner than we think.

But the night also served to remind us of all the good things on this planet, like the mini Titanic reunion that happened when Leo, Kate Winslet, and Billy Zane got together—with the latter taking care to point out the irony in the fact that Leo’s now working to save icebergs:

It was also a hot-spot for a newly single Leo’s favorite thing in the whole wide world besides Citi bikes: models, in this case in the form of Constance Joblanski, Imaan Hammam, Ginta Lapina, Karolina Kurkova, Lindsay Ellingson, and Doutzen Kroes, the latter of whom is an environmental enthusiast herself:

The evening also hosted two performances, the first of which was by Lenny Kravitz, who also paused for a rare selfie with Leo:

But the real star performer was, of course, Madonna, whose surprise performance unsurprisingly stole the show, particularly when Leo and Kravitz joined her onstage:

Among the crowd were more of Leo’s pals, like Adrien Brody:

But unfortunately, like Leo, Tobey Maguire, Sean Penn, and Gerard Butler, who were all also in attendance, go the Leo route in eschewing the platform for anything personal. Alas, that means there’s no further intel on who won the dinner with Kate and Leo the pair auctioned off as part of the gala. From the looks of it, though, it may just have been Billy Zane.

Related: The Year in Leonardo DiCaprio, King of the World

Take a Look Back at Leonardo DiCaprio’s Notorious Dating History: