Elana James came to western swing fairly late and through a circuitous route. She grew up in Kansas where, as a child, she learned classical violin, the instrument of her mother, a concert violinist. During college in New York, Elana switched to viola and played in the New York Youth Symphony and various chamber groups. Her music took a turn when she worked as a ranch hand in Colorado just before her senior year in college. "The rancher had a group called Cowboy Ken and his Ranch Hand Band," she recalls. "I wrangled horses during the day and played fiddle in his band at night." Upon returning to New York in 1994, she began looking for a band and placed an ad in the Village Voice. She met guitarist Whit Smith who was also seeking musicians for his western swing band, Western Caravan. Unfamiliar with western swing, Elana listened to Whit's records by Bob Wills, Hugh and Carl Farr, Cliff Bruner and Milton Brown. Whit also introduced her to the Gypsy jazz of Stéphane Grappelli and Django Reinhardt. Touring with Western Caravan, Elana found improvisation difficult because of her classical background, so she took lessons from veteran violinists/fiddlers Marty Laster and Matt Glaser.

When Whit's band, Western Caravan, broke up, Elana and Whit moved to San Diego, California and busked in Balboa Park, playing fiddle tunes and western standards. They produced a recording as Western Clambake, moved to Austin, Texas and — with the addition of a bass player — became The Hot Club of Cowtown, a tip of the hat both to Grappelli's and Reinhardt's Hot Club of France (Quintette du Hot Club de France) and Bob Wills' Texas Playboys. Within months, Elana was able to meet and play with some of western swing's greatest players: Johnny Gimble, Cliff Bruner, Curly Lewis, and Frankie McWhorter, from whom she learned more tunes. Gimble played on Hot Club's first album and later invited the band to tour with him as his back-up band, including performing at the National Folk Festival in East Lansing in 2001.