Part of filmmaking is always a guessing game, and part of it is always a game of trust.

In 1995 he won the part of David Larrabee in Sydney Pollack's remake of Billy Wilder's 1954 classic Sabrina. Later he would become the creator co-executive producer and host of Best of the Worst which aired from 1990 to 1991. He has two brothers James and Steven.

Notable TV roles include Friends and his Emmy nominated roles for Talk Soup The Kennedys and Modern Family. He has appeared in other notable films including Sabrina You've Got Mail Nurse Betty We Were Soldiers Little Miss Sunshine Invincible and Green Zone.