Frequently acts in movies with John Cusack, such as: Bob Roberts (1992), Elvis Stories (1989), Floundering (1994), The Grifters (1990), Grosse Pointe Blank (1997), One Crazy Summer (1986), The Player (1992), Say Anything... (1989), Serendipity (2001), Runaway Jury (2003).
He got malaria while filming PCU (1994) and had to be rushed to the hospital.
He was also supposed to star alongside his best pal John Cusack in High Fidelity (2000), but had to pull out due to other commitments.
Was considered for the role of Dolarhyde in Red Dragon (2002).
His character Ari in HBO's "Entourage" (2004) is based on real-life Hollywood agent Ari Emanuel.