Sebastian Cole's family is falling apart. His sister is leaving for college in California, his stepfather, the only stable and responsible person in his life, has just announced that he has decided to undergo a sex change, his mother is flipping out, and his absentee father is an all-around jerk.
Sebastian's mother (Margaret Colin) drags him back to her native England to live in a little flat while she descends into a sullen, alcoholic, semi-violent mess. After a few months of this, Sebastian (played by the superb Adrian Grenier) decides to go back to America and give it a shot moving back in with his stepfather Hank, who had offered him a place to stay anytime. This puts Sebastian in a position of living with Hank, (aka. Henrietta) while he begins the hormone regimen and the changes that preface his sex change operation.
Sebastian goes back to his old high school but fudges his manuscript from his school in England so it looks like he has excellent grades and enough credits to become a senior. He stumbles through everything -- school, friendships, relationships, with a mixture of charm, luck, brashness, and a kind of innocent determination.
Sebastian wants to become a writer. When his stepfather tells him he has to get a job and become disciplined about writing, Sebastian retorts that he has to experience things first before he can have anything interesting to write about. Sebastian's goal is to have crazy adventures, and that he does, although some don't turn out quite the way he would like. Adrian Grenier is a very talented actor, and drop-dead gorgeous -- his dark looks flicker between childlike innocence and tortured angst in a way that keeps you glued to the screen. Sebastian Cole is supposed to take place in the 80's and the soundtrack is a great mix of 80's punk and new wave. There's even a cameo by the LES Stitches performing at a punk club Sebastian goes to. This is a great independent movie classic, and Adrian Grenier alone is more than enough reason to rent this immediately.