Since its inception in the late 1990s, the Hot Club of Cowtown has experienced a steady ascent in popularity, becoming known for its remarkable virtuosity and captivating live performances, which have established the band's global presence. Celebrated for its “down-home melodies and exuberant improvisation” (The Times, London), the Hot Club has expertly blended a variety of seemingly divergent musical styles, creating a unique sound that sits “at that crossroads where country meets jazz and chases the blues away” (The Independent). The band is committed to ensuring that “above all else, the music is for dancing and an old-fashioned good time” (New York Times). Its musical approach has been described as “another breathless journey in the Texas tardis” (The Times, London), while American Songwriter has remarked that “the excellent three players of this band could be doing anything but have chosen to honor the greats of jazz and swing with their sound.” The Belfast Telegraph has referred to the Hot Club of Cowtown as “a pretty much perfect country trio at the very top of their game,” and the New York Times, in a live review, noted that the trio is armed with “an arsenal full of technique and joy.”

Over the past twenty-five years, the Hot Club of Cowtown has toured extensively around the globe, both as a standalone act and alongside renowned artists such as Bob Dylan, Willie Nelson, Gatemouth Brown, the Avett Brothers, Dan Hicks, Bryan Ferry, Roxy Music, the Squirrel Nut Zippers, the Mavericks, Dustbowl Revival, and Tyler Hilton. Their festival appearances and career highlights include participation in the Women in Jazz series at Jazz at Lincoln Center, the Cambridge Folk Festival (UK), the Glastonbury Festival (UK), the Fuji Rock Festival (Japan), the Byron Bay Blues & Roots Festival (Australia), the National Folk Festival (in the US and Australia), the Stagecoach Festival, the Winnipeg Folk Festival (Canada), Waiting for Waits Festival (Spain), the grand opening of the Country Music Hall of Fame and Museum in Nashville, Tennessee, The Barns at Wolf Trap, the Rochester Jazz Festival, the Strawberry Festival, the Hardly Strictly Bluegrass Festival, and serving as US State Department Musical Ambassadors in Azerbaijan, Armenia, Algeria, the Republic of Georgia, and the Sultanate of Oman. The band has also been inducted into the Texas Western Swing Hall of Fame.

The origins of the Hot Club of Cowtown trace back to 1994 in New York City, when Elana James placed an ad in the Village Voice seeking to join a band, which was answered by Whit Smith. The music they have created together has consistently embodied a blend of energy, joie de vivre, and respect for tradition that is often imitated but never equaled. By 1997, after founding a larger Western swing orchestra in NYC, Elana and Whit decided to return to their core elements, evolving from the duo “Whit & Elana” into the Hot Club of Cowtown with the addition of a bass player and a spirit of optimism. The trio relocated to Austin, Texas, and released their debut album, Swingin’ Stampede, in 1998 after signing with the American roots label HighTone Records. This was followed by Tall Tales (1999) and Dev’lish Mary (2000). The band’s lineup solidified in 2001 with the arrival of bassist Jake Erwin, who established a robust rhythmic foundation for the group.

Ghost Train (2002) marked the band's shift toward original songwriting, and Continental Stomp (2003) served as a live album recorded at the Hot Club of Cowtown's beloved venue, the Continental Club in Austin, Texas. In 2008, the American label Shout Factory released a 20-track retrospective titled Best of the Hot Club of Cowtown, followed by the album Wishful Thinking (2009). The band began a three-part series of albums dedicated to its roots with What Makes Bob Holler in 2011, featuring Western swing standards popularized by Bob Wills and his Texas Playboys. This was followed by Rendezvous in Rhythm in 2013, which included American Songbook standards and Gypsy-influenced hot jazz reminiscent of Django Reinhardt and Stéphane Grappelli, and Midnight on the Trail in 2016, showcasing re-imagined cowboy ballads, traditional Western swing, and works by Gene Autry, Cindy Walker, Johnny Mercer, Bob Wills, Tommy Duncan, and others. To commemorate their 20th anniversary in 2017, the band re-released Western Clambake, originally available only as a cassette created in 1997 for sales while busking in San Diego’s farmers markets and at Balboa Park. In 2019, they released Crossing the Great Divide, a seven-song EP featuring songs by Robbie Robertson, Bob Dylan, and The Band to honor the 50th anniversary of The Band’s first two albums, Music from Big Pink and The Band. The Hot Club of Cowtown's latest studio album, Wild Kingdom, featuring eleven original songs and three carefully selected standards, was released worldwide in September 2019.

Following Jake Erwin's departure in 2022, the band has incorporated various touring bass players, with Whit Smith and Elana James remaining the only consistent members.