Heyman's credited roles include Private Michael J. Caboose/O'Malley in the popular machinima web-series Red vs. Blue, Wadein The Strangerhood, and Bidderman in 1-800-MAGIC. His writing credits include 1-800-MAGIC and occasional skits in the live action Rooster Teeth Shorts series. In addition to his involvement in machinima, he starred in The Schedule, a live-action film written and directed by Burnie Burns, the creator of Red vs. Blue, and has also done a range of acting roles on American television shows including Friends, Angel, The Inside, Alias, Criminal Minds. He has reprised his Red vs. Blue role as a Blue Prison Guard in the G4 show Code Monkeys, and has had a minor role in Halo 3 as an unseen marine with the voice of Caboose from Red vs. Blue. His character Caboose also has a minor voice role in the Xbox 360 arcade game, The Dishwasher: Vampire Smile. He is also a recurring member of the Rooster Teeth Podcast (previously Drunk Tank). He also has a gaming series on the Rooster Teeth Channel called 'How To', where he and fellow RT Employee Adam Ellis play various video games while under the effects of alcohol.