After the break up of the group Blake in 2008, Cassadee Pope and Mike Gentile decided to keep on playing together, but with a new cast of musicians. After auditions West Palm Beach, Florida, Hey Monday emerged with Cassadee Pope singing lead, Mike Gentile playing lead guitar, Alex Lipshaw playing rhythm guitar, Elliot James playing drums, and Michael "Jersey Moritary playing bass guitar. Hey Monday tickets would sell almost immediately.

The group quickly garnered the attention of Pete Wentz from Fall Out Boy. By the summer of 2008 Hey Monday had recorded their debut album Hold On Tight. The album was released in the fall and peaked at number 11 on the U.S. Heat charts and the number 71 on the Australian album charts. Hey Monday immediately went on tour as a supporting act for groups like The Academy Is…, We The Kings, NeverShoutNever, and The Cab.