Tom began performing at the age of 15. When he turned 19 he began his professional career. At age 20 he became one of the infamous "Outlaw Comics" and his comedy became dark and cutting edge. Tom began to challenge the audience's core belief systems as well as his own. At this point Tom began to grow into an artist not just a stand-up comedian under the strong early influence of Bill Hicks and Sam Kinison.
He began polishing his stand-up routines by touring comedy clubs throughout the United States and in 1991 he won "Austin's Funniest Person" and later the Austin Chronicles "Critic Choice Award."