In 2005, Kelly toured with comedians Dane Cook, Gary Gulman, and Jay Davis on the cross-country tour entitled Tourgasm. After tearing (ACL) and straining (MCL) ligaments in his knee (which led to a crying display ["hold my hand man"], [ I broke my knee man"] that has been often-ridiculed on radio programs such as "The Opie & Anthony Show"), he managed to finish the tour which began airing on HBO as a comedy documentary series in June 2006.^[3] Robert Kelly's alter ego "Billy The Bassman" was introduced on the Opie and Anthony show on February 11, 2011 with the catch phrase "wherewegoin". In 2005 and 2006, Bob Kelly accompanied fellow comedian Colin Quinn to Iraq, where they each performed stand-up for American troops stationed in Baghdad. Kelly claimed on the Opie and Anthony Show, that while there he saw a werewolf.^{[citation needed]}

Robert Kelly also had a cameo in the 2008 paranormal comedy Ghost Town where he plays the ghost of a construction worker.

Robert Kelly was a part of New Jersey's Bamboozle Festival in 2007 as part of the "Pass the Mic Comedy Tour" on Sunday May 6.^[4]

Kelly also had a small voice part in the 2008 video game Grand Theft Auto IV as an Italian gangster that accompanied the main character on a mission.

Kelly was on tour with comedians Al DelBene and Dane Cook on Dane Cook's Global Thermo Comedy Tour: ISolated INcident.

He was featured as Louis CK's brother on season 1 of the FX sitcom Louie.

He is good friends with and former roommate of fellow Boston comedian Bill Burr.