While attending Wellington High School in Wellington, Florida, Pope formed the band Blake with good friend Mike Gentile. The project disbanded before being signed and in 2008, she and Gentile along with Alex Lipshaw, Michael "Jersey" Moriarty, and Elliot James founded the pop punk band Hey Monday. Hey Monday released their first studio album, Hold on Tight, in October 2008. Pope wrote two songs and co-wrote the other nine songs. She appeared in Fall Out Boy's video for "America's Suitehearts", from their 2008 album Folie à Deux. She also provided guest vocals for The Cab's remix version of their song "Take My Hand" that appeared on Fall Out Boy's mixtape, Welcome to the New Administration, and appeared in the music video for it the following summer of 2009. James left the band at the end of 2009. Hey Monday's first EP Beneath It All was to be released in August 2010; to promote the album the group toured the US and played on the 2010 Warped Tour. The Christmas EP was released on December 6, 2011, and later that month Hey Monday took an indefinite hiatus on good terms.
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