Sean Penn Nude

An absolute titan of the acting industry, the beautiful, blue-eyed Sean Penn is a two-time Academy Award winner for his work in Mystic River (2003) and Milk (2008), who may very well add another bald man to his trophy room before he calls it a career. Known for playing intense, deeply flawed characters prone to acts of violence, this powerhouse actor and intuitive filmmaker surprisingly got his start with a short appearance on the farm in a couple episodes of Little House on the Prairie that his dad directed back in 1974. Luckily Sean didn’t stay wholesome for long! After flashing a push-up toned Military school chest that had us squealing "we'd tap that" in TAPS (1981), he went on to play the legendary, checkered Vans wearing, pizza ordering in the middle of class, frequently shirtless surfer-stoner Jeff Spicoli in Fast Times At Ridgemont High (1982). But flash times came when Sean was the bare-butt, balls and pube flashing, Chicago crime kid Mick O’Brien in Bad Boys (1983). Yes, we sure do like ‘em bad! In Racing With The Moon (1984) Sean goes skinny-dipping with Elizabeth McGovern, while in U Turn (1997) we couldn't turn away from a look at his family jewels. You might remember him as Meserve in Casualties of War (1989), Kleinfeld in Carlito's Way (19993), Matthew Poncelet in Dead Man Walking (1995), or as Conrad in The Game (1997), but you'll never forget seeing his ass flexing as he thrusts into future wife Robin Wright in Hurlyburly (1998). Sean's work in I Am Sam (2001) didn't age very well, but Sean's booty did, as shown in 21 Grams (2003). But Sean really gave us our daily dose of Vitamin D in the gay biopic Milk (2008). In Gus Van Sant’s award winning Harvey Milk biopic, Sean shows off his spectacular body, and it does us good. Check out his ass as he grinds on the sexy Diego Luna and see if you can't spot Penn's peen. Yummy! While he's been showing he's still got it in movies like The Gunman (2015), by playing the motorcycle riding actor Jack Holden in Licorice Pizza (2021) and most recently as Nixon's campaign manager John Mitchell on Starz's Gaslit, Sean's mostly a filmmaker these days. He's directed stuff like Into the Wild (2007), Flag Day (2021) and was most recently in The Ukraine filming a documentary about their war with Russia. But in 2021, when Val Kilmer made a documentary featuring a bunch of stuff he'd filmed over the course of his career, we got to see a young Sean mooning the camera while he and Val were working on a play. What a great find. With an amazing body and an intense and focused talent, we've always wished we were Penn's pal.