Underwood has returned to his roots, directing both low-budget films and television. He directed Stealing Sinatra (2003) for Showtime, for which william H. Macy received an Emmy nomination, Back When We Were Grownups (2004) for the Hallmark Hall of Fame which garnered star Blythe Danner nominations for the Golden Globe and the Emmy, and In the Mix (2005), starring R&B singer Usher, Chazz Palminteri and Emmanuelle Chriqui for Lions Gate Entertainment. He directed several holiday themed movies for television: The Year Without a Santa Claus, Holiday in Handcuffs, and Santa Baby. He has directed a number of episodic television dramas, including episodes of Monk, Boston Legal, Reaper, Ugly Betty, Heroes, Chaos, Grey's Anatomy, Burn Notice, Once Upon a Time, Desperate Housewives, Nashville, Scandal, Agents of S.H.I.E.L.D., Quantico and The Good Fight.