Best Adult Comedy movies of 2000s that are award winners or nominees

Actors : Emma Stone, Dan Byrd, Penn Badgley, Amanda Bynes,
Directors : Will Gluck,

A clean-cut high school student relies on the school's rumor mill to advance her social and financial standing.

Actors : Keanu Reeves, Jack Nicholson, Diane Keaton, Amanda Peet,
Directors : Nancy Meyers,

A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age.

Actors : John Cameron Mitchell, Stephen Trask, Theodore Liscinski, Miriam Shor,
Directors : John Cameron Mitchell,

A transgender punk-rock girl from East Berlin tours the U.S. with her band as she tells her life story and follows the former lover/band-mate who stole her songs.

Actors : Jeremy Davies, James Spader, Lesley Ann Warren, Maggie Gyllenhaal,
Directors : Steven Shainberg,

A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.

Actors : Anne Hathaway, Jake Gyllenhaal, Oliver Platt, Judy Greer,
Directors : Edward Zwick,

A young woman suffering from Parkinson's befriends a drug rep working for Pfizer in 1990s Pittsburgh.

Actors : Felicity Huffman, Andrea James, Fionnula Flanagan, Kevin Zegers,
Directors : Duncan Tucker,

A preoperative transgender woman takes an unexpected journey when she learns that she fathered a son, now a teenage runaway hustling on the streets of New York.

Actors : Philip Seymour Hoffman, Emily Watson, Jason Andrews, Adam Sandler,
Directors : Paul Thomas Anderson,

A psychologically troubled novelty supplier is nudged towards a romance with an English woman, all the while being extorted by a phone-sex line run by a crooked mattress salesman, and purchasing stunning amounts of pudding.