Under Allen's direction, Wiest won a well deserved Oscar for Best Supporting Actress, for her brilliant performance as the neurotic, wannabe actress Holly in "Hannah and Her Sisters" (1986). She followed her Academy Award success with performances in "The Lost Boys" (1987) and "Bright Lights, Big City" (1988) before stealing the show from the likes of Steve Martin, Mary Steenburgen, Jason Robards, Keanu Reeves, and Martha Plimpton in Ron Howard's "Parenthood" (1989). Playing Helen Buckman, the divorced mother of two difficult teens, Wiest was both touching and hilarious, and received her second Oscar nomination.

Arguably her most beloved role came as Peg Boggs, the kindly Avon Lady who discovers the titular "Edward Scissorhands" (1990). Wiest returned to Woody Allen in 1994 for "Bullets Over Broadway" (1994), a superb comedy set in 1920s New York, winning her second Best Supporting Actress Oscar for her magnificent portrayal of Helen Sinclair, a boozy, glamorous and neurotic star of the stage, who could made the words "Don't speak!" the funniest sentence ever captured on film. Recently enjoying great success with witchy roles in the film "Practical Magic" (1998) and the TV mini-series "The 10th Kingdom" (2000), Dianne Wiest lives in New York City with her two adopted daughters, Emily and Lily.