- Made his stage debut in a 1977 Philadelphia production of the Steve Allen play The Wake.
- Made his big-screen debut in 1982 dramedy Six Pack, starring Kenny Rogers and Diane Lane.
- Was a regular on sketch-comedy show Saturday Night Live during the 1985-86 season; at 17, he was the youngest person ever to join the cast.
- Following roles in John Hughes' popular teen comedies Sixteen Candles (1984) and The Breakfast Club (1985), reportedly turned down parts the director wrote for him in the back-to-back 1986 hits Pretty in Pink and Ferris Bueller's Day Off.
- Nominated for a 2003 Saturn Award for Best Actor (Television) for sci-fi series The Dead Zone, adapted from Stephen King's novel of the same name.
- Had a cameo as a newscaster in The Dark Knight (2008) and appeared in-character in a viral-marketing campaign for the film.
- 2009, Critics' Choice Awards — Best Acting Ensemble: Nominee
- Thomas Chestaro — Stepfather
- Larry Chestaro — Father
- Mercedes Hall — Mother
- Sandra Guerard — Ex-significant Other
- Teresa De Saint — Ex-significant Other
- Mary Christian — Sister
- Molly Ringwald — Ex-significant Other