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 stepmother, who formerly went by Hank and presented as male, outs herself and announces that she is having a sex change operation.

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".

[4] Stephen Holden of The New York Times praised Adrian Greiner's performance feeling that it "beautifully captures his character's precarious balance of naivete and bravado, self-destructiveness and self-invention".

[6] 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".