Natural July 20, 1963, in Syracuse, New York, Whaley began acting as a teenager. He mass produced his film debut around 1987's Ironweed, and performed mostly inside made-for-TV movies until 1989, when he appeared within Born on the Fourth of July, alongside Tom Cruise. This began an extended collaboration by having director Oliver Stone, including 1991's The Doors (in which he played Robbie Krieger) and, in the equivalent month, JFK (in which he played a machinator in the JFK assassination.)

Above a next deuce years, he played supporting roles within moving-picture show like Hoffa and Swing Kids. He appeared inside his number 1 leading film role inside 1994's Swimming with Sharks, in which he starred paired Kevin Spacey. the resulting season, he played a supporting role as a university student gunned down by Samuel L. Jackson and John Travolta's hitmen in Pulp Fiction.

Inside 1998, he garnered a regular role on the CBS series Buddy Faro. He has as well appeared around episodes of The Dead Zone, Law & Order, and its spinoff Law & Order: Criminal Intent.

He manufactured his directorial debut, Joe a King, around 1999, featuring his Doors costar Val Kilmer and longtime friend and colleague Ethan Hawke in starring roles.