Soon after, Craig Calloway (from Triumph over Tragedy) was added to the Flipside's lineup, and Garrison soon replaced Chris Hill on bass guitar.

The band then supported The Downtown Fiction, All Time Low, Boys Like Girls, Third Eye Blind, and LMFAO on The Bamboozle Roadshow 2010. It was announced that this would be the lead single from The Weekend: Saturday, which was planned to be the continuation from the group's previous EP, The Weekend: Friday.

The band then went on "The Summer Camp for the Dope Awesome Kids Tour", which featured The Scene Aesthetic, The Ready Set, A Cursive Memory and Phone Calls from Home.

In February, the compilation album Punk Goes Classic Rock was released, with the band covering "Crazy Train" by Ozzy Osbourne.

In March, a version of "What Do You Want from Me" with slight editing of the lyrics was used in the ending credits of the film Diary of a Wimpy Kid.

The song was a success and had received many plays and views on the Internet.

The band landed a record deal with Universal Motown Records in April 2007. It was then announced that the band's debut album, Underdog Alma Mater, would be released on April 29.

Burns and Stewart are step-brothers, resulting in Good Day Josif and Triumph Over Tragedy sharing a practice space in their parents' garage.

In 2004, upon the break up of Good Day Josif and Triumph over Tragedy, Cook, Stewart and Burns formed the band the Flipside, along with their friend Chris Hill.

Cook remained on vocals, Turman took on rhythm guitar and vocals, Bello was on bass guitar and vocals, Stewart was on lead guitar, Burns was on drums, and Garrison switched to keyboard.