Underwood began his career as an assistant director and television director. In 1989, he turned with Tremors - Tremors In his first feature film. With City Slickers him his breakthrough.
For Pluto Nash - In the fight against the Mafia moon, he was nominated in 2003 as the worst director for a Razzie. Since then, he has worked mainly for television. He directed several television films and is involved as a director of various series.