Lovett began his music career as a songwriter, but he soon signed with MCA Records in 1986 and released his eponymous debut album. While typically associated with the country genre, Lovett's compositions often incorporate folk, swing, blues, jazz and gospel music as well as more traditional country & western styling. He has won four Grammy Awards, including Best Country Album (1996 for "The Road to Ensenada"), Best Country Duo/Group with Vocal (1994 for "Blues For Dixie" with the Texas swing group Asleep at the Wheel), Best Pop Vocal Collaboration (1994 for "Funny How Time Slips Away" with Al Green) and Best Country Male Vocal (1989 for "Lyle Lovett and His Large Band"). In 1995, Lovett performed a duet of "You've Got a Friend in Me" with Randy Newman for "Toy Story". He plays Collings acoustic guitars.