After issuing self released "Wishbone Saloon" and "Dead Horses", the latter distributed by Lone Star Music, Bingham was signed to Lost Highway Records, who issued his first major label debut with Mescalito on October 2, 2007, produced by former Black Crowes guitarist Marc Ford. Texas Music Magazine has opined that "Bingham talks and sings with a whiskey-and-cigarette throat that screams hard living. Hard in a way that can make a 29-year-old sound like a 50-year-old Tom Waits."
Bingham's bandmates, The Dead Horses, are Matthew Smith (drums), Corby Schaub (guitar and mandolin) and Elijah Ford (bass). The bass player on Mescalito was Jeb Stuart. They appeared with the Drive-by Truckers on the PBS show Austin City Limits in October 2007.
The first single from Mescalito, entitled "Southside of Heaven," was released on November 30, 2007. The next single was entitled "Bread and Water."
Bingham performed two songs for the soundtrack of the movie Crazy Heart, including "I Don't Know," and the theme song, "The Weary Kind." In addition to these performances, Bingham wrote "The Weary Kind" and was produced by T Bone Burnett. He also had a small role in the film as Tony. On January 17, 2010, Bingham was awarded the Golden Globe for Best Original Song for "The Weary Kind" at the 2010 Golden Globe Awards. The song won Best Original Song at the 2010 82nd Academy Awards, as well as Song of the Year at the 9th Annual Americana Music Association awards.
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