In what might be seen as his big break, Rapaport played struggling actor Dick Ritchie in Quentin Tarantino’s "True Romance," which has become something of a cult classic. It's an indelible performance and one that established the basic Rapaport screen persona in many ways.

During the fifth season of "Friends," Rapaport played Gary, Phoebe’s boyfriend. The two share a goofy on-screen connection, and actually move in together — but one day into this arrangement, their relationship ends when Phoebe dumps him for using his service weapon to silence an annoying bird outside their apartment.

One of the best sketches on "Chappelle's Show" is "Popcopy," the print and copy store staffed by people who pathologically don’t care about their jobs. Rapaport appears in the sketch as an employee with a penchant for uncomfortable conversations; he also assures customers the computer system is down, whether it actually is or not.

Rapaport played controversial teacher Danny Hanson on "Boston Public,” and in what is probably the most memorable Danny Hanson storyline, he assigned a book called "The N-Word" after the slur created a violent incident between students. The episode won a Peabody Award in 2002.

In a darker, more nuanced role in the FX crime series "Justified," Rapaport played Daryl Crowe, Jr., head of the notorious Crowe crime family in Florida, who eventually sees his life end in a violent and untimely fashion. Rapaport turned in another memorable performance, but his efforts at a Southern accent received mixed reviews.