The Hot Club's first album, 1998's Swingin' Stampede was a collection of standards, fiddle tunes, and classic western swing songs, including two written by Bob Wills, a major influence on the band. Their 1999 follow-up album, Tall Tales, showcased the songwriting ability of Smith and James with many original songs, including "Darling You And I Are Through" by James, and "Emily" and "When I Lost You" by Smith, as well as more western swing standards by Bob Wills, Pee Wee King, and others. Further albums would continue the same formula of classic western swing and hot jazz, along with originals in the same style. Culminating with Ghost Train (2002), the band's last studio record to date.
The members of Hot Club of Cowtown went their separate ways in 2005, though they reunited for occasional shows in 2006-07, including the Fuji Rock Festival and a tour of Australia as Elana James & The Hot Club of Cowtown, in 2005-06. Whit Smith performed as Whit Smith's Hot Jazz Caravan, based out of Austin, Texas. Elana toured with Bob Dylan in 2005, the first female to be included in his touring band in over 30 years (Elana 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 last name to James (James being derived from her middle name), Elana 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. It was announced that Whit Smith would sit in with James and the Continental Two when they opened for Bob Dylan for a series of shows in the Summer of 2006, again performing at historic ballparks.
By early 2008 the trio had officially re-formed and was touring once more. In August 2008, The Best of the Hot Club of Cowtown was released by Shout! Factory.
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