Sunset Boulevard (1950)

Director: Billy Wilder

B-movie writer Joe Gillis (William Holden) is drawn into a bizarre state of affairs involving desperate, delusional former silent movie star Norma Desmond (Gloria Swanson). Sunset Boulevard is weird, witty, biting, cynical, noir, self-referential, and features uniformly excellent performances. It sits right up there with Wilder's best work, and as such represents some of the very best work Hollywood has ever had to offer.