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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.
It debuted at number 37 on the Billboard Hot 100 and number 7 on the Billboard Hot Country Songs chart. Pope released the lead single, "I Am Invincible" from her upcoming second studio album.
On July 24, 2016, Pope sang the Star Spangled Banner, the United States national anthem, before the Brickyard 400 NASCAR race at the Indianapolis Motor Speedway.
On October 16, 2016, Pope sang the Star Spangled Banner, the United States national anthem, before the Houston Texans and Colts game.
Pope was the lead vocalist of the rock band Hey Monday (on hiatus as of December 2011), with whom she released two studio albums and three EPs.
Pope embarked on a solo career in early 2012, and released the EP Cassadee Pope in May 2012.