'Dawson's Creek' was my introduction to the industry. It put some money in my pocket and it put me in the position I wanted to be in, where I could audition for projects that I wanted to be a part of. I didn't find it creatively fulfilling in any way though.

Under the title "Jimi Pitt and the Twins of Evil" Pitt performed "Hey Joe" with the Twins of Evil for The Dreamers soundtrack. Modeling
In 2012 Pitt was named the face of Italian fashion house Prada to model their men's clothes. A casting agent whom Pitt mistook as a police officer attempting to arrest him noticed him and recommended him for a guest role on the television series Dawson's Creek (he played Henry Parker in 15 episodes between 1999 and 2000).

Pitt is known in film for his role in Bernardo Bertolucci's The Dreamers and in television for his role as Jimmy Darmody in the HBO series Boardwalk Empire.