Lovett’s music career began 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).
Lovett has acted in a number of films, including Robert Altman’s films: The Player (1992), Short Cuts (1993), Prêt-à-Porter (1994), Cookie’s Fortune (1999), and composed for Dr. T & the Women (2000). More recently, he has acted in The New Guy (2002) and Walk Hard: The Dewey Cox Story (2007). His television acting forays include Mad About You, Brothers & Sisters, Castle (TV series), and Dharma & Greg. The Bloodhound Gang’s song “The Bad Touch” does a reference to Lovett: “And you’ll Lovett just like Lyle”. Lovett was given an award called an “Esky” for Surest Thing in Esquire’s 2006 Esky Music Awards in the April issue. The magazine said of Lovett: “The secret of Lyle Lovett’s endurance comes down to the three C’s: class, charisma and consistency… In the studio and on stage with his giant orchestra, he’s spent two decades gracefully matching genuine song craft with A-list musicianship”.
In 2010 Lovett appeared on an episode of Spectacle: Elvis Costello with… which also featured John Prine and Ray LaMontagne.
Lovett has recently contributed a cover of Buddy Holly’s “Well… All Right” for the tribute album Listen to Me: Buddy Holly, released on September 6, 2011.
In 2013 Lovett appeared in Episode 2 of The Bridge, an FX series, as Flagman, a lawyer.
Lovett’s personal life was brought to the fore in 1993 when he married actress Julia Roberts. The couple had met on the set of The Player in 1992. After a three-week romance, they eloped and married in June 1993 in Marion, Indiana. The couple divorced less than two years later, in March 1995. People Magazine reported that the breakup was caused by career demands.   The two remained friends afterwards.
Lovett became engaged to his former personal assistant April Kimble in 2003[6] but they remain unmarried.
On March 28, 2002 Lovett was caught by a bull and rammed into a fence on his uncle’s farm in Klein, Texas, before being pulled to safety. He fully recovered after six months and began touring again in the summer of 2003.
Lovett was conferred the honorary degree of Doctor of Humane Letters by the University of Houston on May 15, 2010 at its general commencement ceremony.[7][8] His mother was in the audience as her son was presented with an honorary doctorate from the same university she had received her bachelor’s degree in 1960.[9] His late father was also a graduate of the University of Houston.