Middlebrooks worked on The Suite Life on Deck, Hannah Montana, My Name is Earl, and Chocolate News.

He appeared in HBO's Entourage and portrayed a recurring character in the ninth season of Scrubs.

He also appeared on It's Always Sunny in Philadelphia as a character who marries a transgender ex-love of Mac and has a child with her, of which Dee is the surrogate mother.

He appeared as a regular cast member in the medical/procedural drama television series Body of Proof, playing an assistant coroner.

[6][non-primary source needed][7][8] On March 9, 2015, Middlebrooks was found unconscious at his home in the San Fernando Valley, pronounced dead on arrival at a Los Angeles hospital.