DiMaggio began acting in children's theatre in his native New Jersey, but after studying drama in college, his earliest break came as a stand-up comedian. As half of the hip-hop-influenced beat-boxing double act Red Johnny and the Round Guy (he was Johnny), DiMaggio was a contemporary on the New York comedy scene with fledgling stand-up performers like Dave Chappelle, Jay Mohr and Sarah Silverman for six years. When the act split up, DiMaggio made the move to Los Angeles and resumed his acting career. He made his television debut on a 1996 episode of "Law & Order" (NBC 1990-2010) and his first film appearance as a construction worker in the Whoopi Goldberg vehicle "Eddie" (1996). His first major TV role came as the recurring character Dr. Sean Underhill on the hospital drama "Chicago Hope" (1994-2000). DiMaggio initially began working as a voice-over artist while still living in New York as a way to pay the bills between acting gigs, and continued to seek work in the field after moving to Los Angeles. However, his casting as Bender in "Futurama" was a serendipitous accident: he had already auditioned and been accepted for a role as a cast member of the Fox late night sketch-comedy show "MADtv" (1995-2009), but had decided to turn the show down on the advice of his agent. Undeterred, the same casting crew asked him back to read for the roles of both Bender and Professor Philo T. Farnsworth on Matt Groening's "The Simpsons" follow-up "Futurama." The gravelly mix of pathos and aggression in DiMaggio's portrayal of the hard-gambling, human-hating robot Bender would go on to be one of the most popular cult television characters of the early 2000s, with many of the robot's sardonic witticisms making it onto t-shirts and bumper stickers.With his name in the credits of one of the critically-acclaimed animated hits of the day, DiMaggio's list of voiceover credits soon boomed in both television and film. Among his highest profile appearances were the film "Dr. Doolittle 2" (2001) and the animated television shows "Samurai Jack" (Cartoon Network 2001-03), playing a particularly convincing and memorable role as The Scotsman. As Bender, he also transferred to Groening's other famous creation "The Simpsons" (Fox 1989-) for a one-off "Futurama" crossover episode.His voice skills transferred to a third career voicing video games including entries in the "Final Fantasy" and "Halo" series. Amongst gamers he was best known as the lead character Marcus Fenix from the "Gears of War" series, while fans of comic book characters heard him voice supporting characters in animated shows and video games featuring Spider-Man, Superman, The Avengers, The Incredible Hulk and X-Men, although his most celebrated appearance in this genre was as Aquaman in the series "Batman: The Brave and the Bold" (Cartoon Network 2008-11). Having remained with "Futurama" through its cancellation in 2003 and its subsequent revivals, first as a series of TV movies in 2007, then with all-new episodes from 2010 to 2013, DiMaggio's career continued to display hard-working versatility outside of his most famous role. High-profile voice parts as leading characters in the film spinoff "The Penguins of Madagascar" (Nickelodeon 2008-15) and "Adventure Time With Finn & Jake" (Cartoon Network 2010-) competed with roles in big-budget animated films such as the sequels "Madagascar: Escape 2 Africa" (2008) and "Madagascar 3: Europe's Most Wanted" (2012), as well as "Wreck-It Ralph" (2012).