Marked by their versatility, Chicago-based roots rock band the Empty Pockets have a style of their own, but have also learned the ropes from working with a wide swath of other talented artists including veterans like Dave Mason, Kenny Loggins, and Al Stewart. Formed in the late 2000s by cast members of a Buddy Holly musical, the group nurtured a strong independent spirit while earning a loyal fan base through releases like 2011's Introducing the Empty Pockets and 2015's self-recorded The Ten Cent Tour. Throughout the latter portion of the 2010s, the Empty Pockets juggled national tours while remaining an active studio band, issuing various EPs and the full-length set Tanglewoods in 2019.
The group was founded in 2006 by guitarist and singer Josh Solomon, who grew up in Lincolnwood, Illinois, a suburb less than 15 miles from Chicago. Solomon first started playing music with a pair of childhood friends, bassist Nate Bellon and drummer Danny Rosenthal, and when Solomon was cast as iconic '50s rocker Buddy Holly in a Chicago production of the musical Buddy: The Buddy Holly Story, Bellon and Rosenthal tagged along, landing the roles of Holly's backing band, the Crickets. During the run of the show, Solomon, Bellon, and Rosenthal cut an album of Buddy Holly covers, Not Fade Away, that they released under the moniker Josh & the Empty Pockets.
After the run of the show was over, Josh & the Empty Pockets began playing the Chicago club circuit, performing both covers and original material with the addition of Erika Brett, a keyboard player and vocalist who had also appeared in the Chicago production of Buddy and occasionally appeared with the group. Brett appeared on two tracks of the second Josh & the Empty Pockets album, Under the Bed, in 2008. The set features ten original tunes, all of which would be featured on various Nickelodeon TV shows. By the end of 2008, Brett had become a full member of the group, with the name streamlined to the Empty Pockets as they released a holiday single, "Baby, It's Cold Outside" b/w "Baby Please Come Home."
A six-song EP, Introducing the Empty Pockets, arrived in 2011, while the band closed out the year with another Yuletide release, a five-song set entitled A Holiday Staycation with the Empty Pockets. When not busy recording in their personal studio, the Empty Pockets played out frequently, headlining clubs and opening for Bob Schneider, Dave Mason, and Dickey Betts, among many others. They also served as backing band for a number of artists of note, including Kenny Loggins, Al Stewart, Gary Wright, Richie Furay (of Buffalo Springfield), and Simon Kirke (of Bad Company). In 2015, the Empty Pockets returned with a new full-length album, The Ten Cent Tour, expanding their sound into various facets of Americana and entering both the Billboard Heatseekers and Indie charts. With the 2017 release of the eight-song project Voices, the Empty Pockets entered a particularly prolific period, releasing another holiday EP, Snow Day, in 2018, followed a year later by both a new studio album, Tanglewoods, and the concert album, Live in Seattle.