Lovett's songs and distinctive vocal stylings have graced films ranging from Steven Spielberg's "Always" (1989) and Ivan Reitman's "Fathers' Day" (1997) and it was only a matter of time before he moved in front of the cameras. He made a memorable feature debut as an offbeat police detective in Robert Altman's scathing Hollywood satire "The Player" (1992). Lovett went on to appear in two more Altman features, "Short Cuts" (1993), playing a disturbed baker who harasses Bruce Davison and Andie MacDowell, and "Ready to Wear (Pret-a-Porter)" (1994), as a boot manufacturer. He co-directed the comedy short "Penguins" (1994), played a supporting role as the title character's uncle in "Bastard Out of Carolina" (Showtime, 1996) and landed a romantic role opposite Lisa Kudrow in "The Opposite of Sex" (1998).

Despite his success as a singer and his burgeoning acting career, Lovett is perhaps best recalled for his brief marriage to actress Julia Roberts in 1993.