"Strangers with Candy" 1999

Synopsis:

Jerri Blank is a former prostitute and junkie whore who returns to high school as a 46-year-old freshman at Flatpoint High. Jerri ran away from home and became 'a boozer, a user, and a loser' after dropping out as a teenager, supporting her drug habits through prostitution, stripping, and larceny. She has been to prison several times, the last time because she 'stole the TV'. At home, Jerri's father Guy is comatose, although he seems perfectly capable of amazing feats. Her stepmother Sara is vain and bitter, and stepbrother Derrick is a bullying jock. Jerri tries to do things the right way but always ends up learning the wrong lesson. Her hijinks often involve, either directly or indirectly, neurotic history teacher Chuck Noblet and his secret lover, sensitive art teacher Geoffrey Jellineck.

Tagline: Doing things right....the second time around.
Cast:
Amy Sedaris
Amy Sedaris
Jerri Blank 
Paul Dinello
Paul Dinello
Geoffrey Jellineck 
Stephen Colbert
Stephen Colbert
Chuck Noblet 
Greg Hollimon
Greg Hollimon
Onyx Blackman