He made his New York stage debut in the off-Broadway show Rockabilly Road at the West Bank Theater.
New York filmmaker Abel Ferrara saw one of Hipp's shows and asked him to audition for the role of Nino Valacci in his upcoming film China Girl.
Hipp landed the role, and a decades-long collaboration began as he became a mainstay in Ferrara's core group of actors that includes Christopher Walken, Harvey Keitel and Willem Dafoe.
Buddy opened to rave reviews on October 12, 1989, at The Victoria Palace Theatre, and Hipp was nominated for the Laurence Olivier Award for Outstanding Performance by an Actor in a Musical.
In 2000, Hipp made his feature film directorial debut with Death of a Dog, which stars Julie Kessler and Edie Falco, executive produced by Ferrara.
In 2006, for The Huffington Post, Hipp wrote a blog with videos that included satirical musical parodies like his take on Johnny Cash's "Folsom Prison Blues" (with Dick Cheney singing about his hunting mishap) and The Beatles' "I Am the Walrus" (a take-off of George W. Bush's "I’m the Decider" quote).
He wrote and recorded an album of songs culled from his work for The Huffington Post, called Blog of War.
[7] He also released a CD of songs from and inspired by the film No Somos Animales, called Buenos Aires, in the fall of 2015.