Sebastian Cole

The Adventures of Sebastian Cole is a 1998 American comedy-drama film written and directed by Tod Williams and starring Adrian Grenier as the title character.

In June 1983 in Dutchess County, New York, Sebastian Cole's stepfather, Hank, drops a bomb: he announces that he is having a sex change operation. Sebastian's sister, Jessica, leaves immediately for California, and his mother, Joan, takes him back to England. Eight months later, Sebastian is back in New York, knocking on Hank's door. Hank (now Henrietta) takes Sebastian in and supports him over the next few months of high school. Sebastian's "adventures" are mostly self-destructive.

• Adrian Grenier as Sebastian Cole
• Clark Gregg as Hank/Henrietta Rossi
• Aleksa Palladino as Mary
• Margaret Colin as Joan Cole
• John Shea as Hartley
• Marni Lustig as Jessica Cole
• Joan Copeland as Grandma Cole
• Tom Lacy as Grandpa Cole
• Gabriel Macht as Troy
• Russel Harper as Wayne
• Rory Cochrane as Chinatown
• Famke Janssen as Fiona
• Nicole Ari Parker as Nurse Jenny
• Marisol Padilla Sánchez as Woman in Desert
• Levon Helm as Bob

The film received mixed to negative reviews; it currently holds a 43% "rotten" rating on Rotten Tomatoes. The film critic Roger Ebert gave the film three out of four stars, noting that the film avoids easy cliche in favour of a more thoughtful approach to the subject matter. He gave particular praise to Clark Gregg saying that, whilst one is never in doubt about his gender because of his physical appearance, "in his heart he knows he is a woman, and he is true to that inner conviction with a courage that the film doesn't need to underline, because it permeates the performance". Stephen Holden of The New York Times praised Adam Greiner's performance feeling that it "beautifully captures his character's precarious balance of naivete and bravado, self-destructiveness and self-invention".

Writing in Variety, Joe Leydon believed that the scenes between Gregg and Grenier were the strongest (although he felt that Gregg's portrayal came close to caricature). He was critical of the technical aspects of the film's production, felt that other films had covered similar ground better and that the ending was poorly conceived and too abrupt. He predicted that the film would perform poorly with critics and at the box office. Entertainment Weekly's Owen Gleiberman gave the film a "B" rating, adding that he wished it had been better structured, although the current configuration was "integral" to its "charm".