The Hot Club of Cowtown formed in 1996 as a Hot Jazz/Western swing group. The group consisted of Elana James nee Fremerman (Vocals, Violin), Whit Smith (Vocals, Guitar), and Jake Erwin (Vocals, Upright Bass).

The Hot Club's first album, 1998's Swingin' Stampede, was a collection of covers of classic tunes, including two written by Bob Wills, a major influence on the band. Their 1999 follow-up album, Tall Tales, showcased the songwriting ability of both Smith and Fremerman, with many original songs, including "Forget-Me-Nots" and "That Secret of Mine," both by Fremerman, and "It Stops With Me," by Smith, mixed with covers ranging from Rodgers and Hart's "You Took Advantage of Me" to Aerosmith's "Chip Away the Stone." Further albums would continue the same formula of classic western swing and hot jazz, along with originals in the same style.

The Hot Club of Cowtown broke up in 2005. Whit Smith and Jake Erwin performed together as part of Whit Smith's Hot Jazz Caravan, based out of Austin, Texas. Elana James toured with Bob Dylan in 2005, the first female to be included in his touring band in over 30 years (she came to Dylan's attention when The Hot Club of Cowtown opened for him and Willie Nelson during a joint tour of historic ballparks in the Summer of 2004). Changing her name to Elana James, Fremerman began performing in late 2005 with Beau Sample (formerly of Cave Catt Sammy) and Luke Hill, first under the name Elana James and Her Hot Hot Trio, and later as Elana James and the Continental Two. The band reunited in 2008.