Montgomery was born in Indianapolis, Indiana. He graduated from Ball State University with a degree in performance theater and drama. Montgomery did stand-up comedy briefly after graduation, before moving to California.
Sometimes credited as "A.T. Montgomery", his first starring role was in the horror-comedy Leprechaun in the Hood (2000), for which he also contributed writing and vocals for several songs. He had a recurring role on the television series Popular before being cast in Star Trek: Enterprise in 2001. In 2004, he returned to stand-up comedy.
Montgomery starred in the film I'm Through with White Girls in 2007. In January 2009, Montgomery appeared in an episode of the Fox series House. In 2013, he appeared briefly as a dud romantic-interest in the show Baby Daddy (season 2, ep. 1), playing a handsome but boring drycleaner the show's (young) grandmother was interested in. In 2013 he also produced and starred in the independent film Chariot, about seven amnesiac strangers who awake on an airliner mid-flight.

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