Cannes Film Fest 2021: Sean Penn, Two-Time Oscar Winner, and his Cannes Fest History

Two-time Oscar winner Sean Penn, who’s 60, appears at Cannes this year with his latest directorial effort, Flag Day, starring his daughter, Dylan Penn, Josh Brolin and Miles Teller.The movie plays in the Main Competition, where several of Penn’s previous films (good and bad) had appeared.In 2008, Penn had served as president of the jury at Cannes, honoring the French movie, Laurent Cantet’s Entre Les Murs, with the top kudo, the Palm d’Or.

But the history of Penn and Cannes is long and rich, going back to the early 1980s.

There’s an interesting backstory to how Penn, then 23, wound up hanging out with Robert De Niro, then 40, at the 1984 Cannes Film Fest.

Penn was a young actor at the time whose best known work was as the surfer Jeff Spicoli in the teen comedy Fast Times at Ridgemont High.


One day, Penn spotted Harry Dean Stanton, then 57, sitting at the bar in the Sunset Strip and struck up a conversation.

“He regarded me highly,” Stanton later said. “And I was intrigued by him.”

Stanton mentioned he was heading to Cannes to attend the festival, where — unbeknownst to him — his film Paris, Texas would go on to win the Palme d’Or.

Penn asked if he could join him, to which Stanton replied, “Uh, OK.” So the two flew together to France. “All he brought with him was passport and toothbrush,” Stanton later recalled. The duo shared a hotel room for five days, at which point Stanton wanted some privacy and suggested Penn find new lodging.

Penn then ingratiated himself with De Niro and Joe Pesci, who were there supporting Sergio Leone’s Once Upon a Time in America. De Niro paid for a room at the Hotel du Cap for Penn.