Heyman's credited roles include Private Michael J. Caboose/O'Malley in the popular machinima web-series Red vs. Blue, Wadein The Strangerhood, Bartholomew Oobleck in RWBY, 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. 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 The Drunk Tank). He also has a Rooster Teeth gaming series on called How To, where he and fellow employee Adam Ellis play various video games while under the effects of alcohol. He also had a small but pivotal role in a Rooster Teeth film Lazer Team as a on field news reporter.