According to Frontiers Records, Cherone teamed up with his brother Mark to write his most succinct record to date.

"Hurtsmile was a long time coming… I always wanted to write a record with my brother," says Gary. "I'm a big fan of Mark's song writing and his snarling guitar riffs." The timing was right as Extreme was in-between their touring and record cycle, leaving Gary the freedom. They recruited Joe Pessia (bass) an alumnus of Nuno Bettencourt's Dramagods as well as the guitar player for Tantric. Joe also engineered, and co-produced the record with Gary. To round off the lineup they enlisted heavy hitter Dana Spellman on drums "It's an east coast-Boston thing," states Gary. "Mark, my brother, was in a band with Nuno's brother… Joe was in Nuno's band and Dana was a friend, and student of Mike Mangini (former Extreme drummer) … we like to keep it in the family."

The lineup is not the only thing familiar with the band. In true Cherone fashion, the record is chock full of swaggering guitar, soaring vocals and the trademark Cherone eclecticism on tracks such as "Jesus Would You Meet Me", the reggae-tinged "Just War Reprise" and the Dylanesq "The Murder of Daniel Faulkner (4699)". "Hurtsmile was about returning to my roots, writing a record in my basement, a straight up rock 'n' roll record… but it turned out to be more diverse and ambitious than I expected."

Gary is no stranger to taking on intense topics, and Hurtsmile is no exception. The first half of the record is a group of more loosely knit songs such as the cynically inquisitive "Just War Theory", the limit's of free speech "Tolerance Song (edit)" and the disturbingly mesmerizing "Kaffur (Infidel)", inspired by the beheading of Daniel Pearl.

The 2nd half of the record is more conceptually cohesive; an introspective look at the nature of man and the condition of the human heart. "Stillborn" introduced earlier, and "Set Me Free" both touch on mans inclination toward darkness, culminating with an epic journey from sin to salvation… "Slave" to "Beyond the Garden/Kicking Against the Goads".