WTF Happened to Sean Penn?

Very few personalities in Hollywood are as controversial as Sean Penn. One of the most gifted actors of his generation, Penn’s also been a lightning rod for controversy, with his often antagonistic relationship with the press and sometimes misguided moves, such as his now infamous interview with drug baron El Chapo. Yet, he’s also a noted humanitarian, participating in rescue efforts in the wake of Hurricane Katrina and being a tireless advocate for Haiti following the 2010 Earthquake. He’s also been an outspoken supporter of Ukrainian president Zelensky.

In this episode of WTF Happened to this Celebrity, we look at the scope of Sean Penn’s career. We chart his earlier days as perhaps the most talented young actor to emerge in the early eighties, stealing scenes in Taps and later becoming a star thanks to turns in movies like Fast Times at Ridgemont High, At Close Range, The Falcon and the Snowman and the controversial Colors. We look at some of his missteps, such as when he became a tabloid fixture during his marriage to Madonna and his disastrous film Shanghai Surprise. In the nineties, Penn, who many thought was washed up, had a tremendous resurgence by taking on character roles in Carlito’s Way, Dead Man Walking and The Game before winning two Best Actor Oscars, first for Mystic River in 2003, then for Milk in 2008. He also became a noted director, having helmed The Crossing Guard, The Pledge, and Into the Wild. However, he also had a few flops in that regard, such as the notorious The Last Face, starring Charlize Theron and Javier Bardem.

Recently, Penn has shown up in small roles in movies like Licorice Pizza and on TV in the limited series Gaslight. It seems, for many, his acting career has taken a backseat somewhat in recent years. In this episode of WTF, written (with Mathew Place), narrated, produced and edited by Taylor James Johnson, we dig into his career, future plans and more. What’s your favorite Sean Penn role? Let us know in the comments.