His various voice roles include Bender on Futurama, Jake the Dog on Adventure Time, Marcus Fenix in the Gears of War series, Dr. Drakken on Kim Possible, Hak Foo in Jackie Chan Adventures, The Scotsman on Samurai Jack, Brother Blood on Teen Titans and Teen Titans Go!, Shnitzel on Chowder, Fu Dog on American Dragon: Jake Long, Hammerhead and Sandman on The Spectacular Spider-Man, Aquaman on Batman: The Brave and the Bold, King Zøg on Disenchantment, Jocktopus on Fish Hooks, Wakka and Kimahri in Final Fantasy X, Rath in the Ben 10 franchise, Crosshairs, Leadfoot, Nitro Zeus, Transit and Stratosphere in the Transformers film franchise, and Gonza in the English version of Princess Mononoke.

[5] DiMaggio is known for his roles as Bender on Futurama, Marcus Fenix in the Gears of War franchise, Dr. Drakken on Kim Possible, Jake the Dog on Adventure Time, Wakka and Kimahri in Final Fantasy X, and Niblet on Pound Puppies.

He is a former comedian, appearing on stage as part of a comic duo named "Red Johnny and the Round Guy" and has several on-screen credits, such as Steve Ballmer in Pirates of Silicon Valley (the docudrama about the history of Apple Computer and Microsoft) and as Dr. Sean Underhill, a recurring character on Chicago Hope.

[7] In 2022, upon news that Futurama would be revived for a second time through Disney and Hulu, DiMaggio ran into conflict during negotiations while demanding more money to reprise the role of Bender, which he dubbed "#BenderGate".

He revealed that though he did not succeed in negotiating a pay increase, he felt the attention to the issue of proper compensation in the voice acting industry was worthwhile.