In late 1995, Joe Sib after the break up of his band Wax, decided to get together with long time friend Steve Soto (former member of The Adolescents and Agent Orange) to write some material. They started writing songs and soon noticed that something special was taking place. They soon gathered Sandy Hansen (The Adolescents), Scott Shiflett (Face to Face), and Jason Cropper (Weezer) to form 22 Jacks. In February 1996, 22 Jacks went to The Sandbox studio in Los Angeles and recorded 12 songs which became the "Uncle Bob" record. With the three final additions to the band already having prior commitments, Sib and Soto went on a search for replacements to solidify the lineup. They found Kelly LeMieux Fear, Jose Medeles (The Breeders, and Face to Face), and Bill Fraenza.

efore a fourth album could be recorded, 22 Jacks called it quits around 2001 as Sib left the band to concentrate on the future of SideOneDummy Records. Following the breakup, Soto went on to reform The Adolescents and Medeles also joined the reunion of The Breeders as their new drummer.

During its six year lifespan 22 Jacks toured with numerous bands, including Reel Big Fish, The Bloodhound Gang, Mighty Mighty Bosstones, Goldfinger, Social Distortion, Bouncing Souls, Unwritten Law, Face to Face, Voodoo Glow Skulls, and Ten Foot Pole. They also sang back up for Joey Ramone on a song for a Cheap Trick Tribute album. This helped spark a friendship that lead to Joey Ramone showing up at 22 Jacks concerts and even singing a song or two with them.