Montgomery is the grandson of jazz musician Wes Montgomery. He graduated from either Ball State University with a degree within performance theater & drama. Montgomery did could have-higher comedy briefly fallowing graduation, prior to moving to California. He got the revenant role on the television series Popular before being cast within Star Trek: Enterprise inside 2001.

Inside 2004 he returned to the stage within Los Angeles, producing his have indicate, besides when giving to have-higher comedy. within the summertime of 2005, he returned to Indiana to star in theatrical fundraisers for charity.

Montgomery has produced 1 Video of his have music, "What You Know About...", featuring iv songs all about "Star Trek" themes. He occurs as frequent guest at "Star Trek" conventions.