Underwood made his feature film debut in 1990 with the science fiction comedy Tremors. In 1991, he directed the multi-award-winning box office hit, City Slickers, followed by Heart and Soul and Speechless. In 1998, he directed the remake of the 1949 classic Mighty Joe Young, which earned an Oscar Nomination for Best Visual Effects. Stealing Sinatra (2003) received an Emmy nomination and Back When We Were Grownups (2004) received Emmy and Golden Globe nominations. He recently directed the movies for television The Year Without Santa Claus and Holiday in Handcuffs. Underwood has also directed many critically-acclaimed television series, including Monk, Boston Legal, and Ugly Betty.