Sean Penn took a drag off his cigarette, stared down at his work boots and conceded that, as political activism goes, he’s not usually on the side that wins. “I am a person who does care,” Penn said, sitting in his trailer backstage, “but I have only ever failed.” He started rattling off his activism resume — candidates he has supported, the war he has opposed, the policies he has protested. “But I am an optimist and this young generation right now is so much smarter than us. That’s why we’re here.”

Penn spoke twice Sunday, including an early evening speech on the main stage, where he looked out over a huge and somewhat puzzled audience. “It was nerve-racking, public speaking is not my thing.”

Coachella founder Paul Tollett reached out to Penn a few weeks ago (mutual pal Rosanna Arquette helped the two connect) to ask him to speak. The reason: Both agree that the MySpace Generation is the most connected ever, but somehow also becoming the most isolated. Penn came to invite them “to turn off their computers and come see some things in the world in person.”

Penn’s plan is to take a convoy of buses to New Orleans on a 10-day tour that will make multiple stops along the way to give his band of Coachella fans a tune-up in activism. They will protest the war, talk up green issues and, in Louisiana, do some construction work to help the still-beleaguered congregation of a church that was destroyed by Hurricane Katrina. As of 8 p.m. Sunday, there were more than 100 people signed up for his Dirty Hands Caravan. “Paul called me up and said he didn’t want the young fans at this festival to be asked by their grandkids someday ‘What did you do during the war?’ and have to answer, ‘I had a MySpace page.’ This generation is smarter, funnier and better than the 1960s generation and the generation I grew up with. This is a chance to tap into their imaginations.’”

– Geoff Boucher