While directing and producing short films for the educational market, Underwood pursued work in the motion picture industry.

In 1986 Underwood established himself as a director when his live action/stop motion film adaptation of Beverly Cleary's The Mouse and the Motorcycle won a Peabody Award, which was followed two years later by the sequel Runaway Ralph, for which he received a Daytime Emmy nomination.

His first effort was Tremors[1] starring Kevin Bacon, Fred Ward, Michael Gross, and Reba McEntire in her acting debut.

Underwood received his first taste of commercial success with 1991's City Slickers, which starred Billy Crystal, Daniel Stern, Bruno Kirby and Jack Palance, who won an Academy Award for his performance.

His next film, also written by Maddock & Wilson, Heart and Souls (1993), was again well-received by critics but struggled at the box office (making a total of $16m in the US).

It starred Robert Downey, Jr., Alfre Woodard, Kyra Sedgwick, Charles Grodin, Tom Sizemore, Elisabeth Shue and David Paymer.

Following Mighty Joe Young, Underwood began work on the Eddie Murphy fronted The Adventures of Pluto Nash.

He has directed many television dramas, including episodes of Monk, Boston Legal, Ugly Betty, Heroes, Grey's Anatomy, Burn Notice, Once Upon a Time, Desperate Housewives, Nashville, Scandal, Agents of S.H.I.E.L.D., The Good Fight, Big Shot, Fear the Walking Dead, Evil, Watson and Elsbeth.