Josh & The Empty Pockets released a Buddy Holly Tribute album in 2007 and Under the Bed in 2008, with Erika Brett featured on two of the songs.

The band also recorded an acoustic version of the song at Sweetwater Studios included with a second previously unrecorded song called "Leaving Jackson" on WAJI's annual charity CD, a fundraising project for Riley Children's Hospital, with other notable artists including Ingrid Michaelson, Gavin DeGraw, Uncle Kracker, Vertical Horizon and Eric Hutchinson, among others.

"[3] The song peaked the week of Christmas 2008 and reached #51 on the Mediabase AC chart playing on radio stations across the United States.

[22] After signing, promotion of the single "Fall Right Now" to major radio markets got underway, which saw it receive airplay on a number of Clear Channel and other monitored stations.

[23] During March and April the single appeared twice on Mediabase's weekly Taking Off airplay chart, which lists "the Top 50 currents by most new spins, showing detections for the first time."

Solomon’s smooth pop vocals possess a newfound throaty gusto, while Brett’s bring a sort of polished abandon to the proceedings.

“Leaving Jackson” is a heartwrenching ballad with Brett's vocals taking on a world-weary croon backed by chiming, shimmering guitars and a driving backbeat.

Showcasing the group's understanding of songcraft rather than any individual member, the song is a reminder of the fun we can have when we have nothing else–and possibly a perfect summary of The Empty Pockets as a band.

Beyond the obvious Buddy Holly influence, the new batch of songs bring to mind modern Americana tentpoles like Drive-By Truckers, soul studio legends like Raphael Saadiq, fellow Chicago greats like JC Brooks & the Uptown Sound, and 1990s pop-rockers such as Blues Traveler.

Such a laundry list of obvious influences might make the group sound derivative on paper, but the resulting handcrafted rock ‘n roll is fresh yet familiar, exciting yet comfortable.

[35] On October 5, 2010, The Empty Pockets played at the House of Blues for Michigan Avenue Magazine's second anniversary party, which also featured performances by Jennifer Hudson and DJ Rock City.

[46][47] In October 2013, Josh was selected to participate in the Sunset Sessions Alumni Songwriting Retreat in Tulum, Mexico with Mark Bryan from Hootie & the Blowfish, Bob Schneider, Louise Goffin, Tristan Prettyman and members of the Parlotones.

[54] Rolling Stone said of the collaboration, "Though he's hung his hat in New York City for years, Kirke shows an enviable rapport with bandmates Josh Solomon, Erika Brett, Nate Bellon and Danny Rosenthal, members of polished yet rootsy Chicago outfit Empty Pockets.

"[55] The band has also backed up Kenny Loggins, performing his hits, as well as sharing Empty Pockets' original material as part of the SoundExchange Influencer's Series.

[57] Echoing the sentiments of prior reviews, Amy Lotsberg, a music critic and producer of Collected Sounds, wrote "Josh Solomon has a pleasing voice.

"[59] Peter Jurew & Lou Montesano of Elmore Magazine opine, "worthy of mention are the Empty Pockets, a tight and soulful quartet who are much more than just a backing band.