I kind of told somebody I'd do a Woody Allen post, so let's get to it.
(All five feature Allen as a triple threat: actor, director, and writer (or co-writer).)
Take the Money and Run (1969): The life and times of Virgil Starkwell, inept bank robber. This is the film that put him on the map. Before this, people had to stop at the gas station and ask directions. With Janet Margolin.
Annie Hall (1977): Neurotic New York comedian Alvy Singer falls in love with the ditsy Annie Hall. This is my favorite Woody Allen film. Oscars for Best Picture, Best Director (Allen), and Lead Actress (Diane Keaton). With Tony Roberts and Paul Simon.
Broadway Danny Rose (1984): In his attempts to reconcile a lounge singer with his mistress, a
hapless talent agent is mistaken as her lover by a jealous gangster. With Mia Farrow and Nick Apollo Forte.
Crimes and Misdemeanors (1989): An ophthalmologist's mistress threatens to reveal their affair to his
wife, while a married documentary filmmaker is infatuated by another
woman. This is my favorite of his "darker" films. With Martin Landau and Sam Waterston. Allen was nominated for a Best Director Oscar and Landau for Best Supporting Actor.
Manhattan Murder Mystery (1993): A middle-aged couple suspects foul play when their neighbor's wife suddenly drops dead. Golden Globe nomination for Diane Keaton. With Alan Alda and Anjelica Huston.