Sixteen Deluxe formed in 1994 after the demise of Swingset, a band that featured vocalist/guitarist Carrie Clark, bass player Owen McMahon (Cherubs, Butthole Surfers), and drummer John Paul Keenon (Sean Lennon).

Enlisting bass player Jeff Copas and drummer Lyman Hardy (Ed Hall), Sixteen Deluxe began rehearsing in the spring of 1994.

After writing and playing throughout the summer of 1994, Sixteen Deluxe were asked by King Coffey (Butthole Surfers) to record a 7" single for his Trance Syndicate label.

Released in May 1995 by Trance Syndicate and distributed by Touch and Go Records, Backfeedmagnetbabe was met with positive critical acclaim and brought the band to the attention of major labels.

The band recorded their Warner's debut at Hyde Street Studios in San Francisco during January and February 1997 with producer John Croslin, engineer Dave McNair, and new drummer Steven T. Hall.

Sixteen Deluxe asked to be released from their Warner Bros. contract in November 1998, and after receiving a settlement from the label built their home studio, The Bubble.

In November 1999 while on tour, Copas quit the band in Lawrence, Kansas, and drummer Steven T. Hall replaced him on bass, with Kliph Scurlock (Flaming Lips) taking over drums.

In September 2012, they performed at Grulkefest, a benefit for the late Brent Grulke, Creative Director of SXSW, along with Austin bands True Believers, The Reivers, and Fastball.