This song was inspired by the famous bandleader Benny Goodman, whose story captivated Saint Motel lead singer A/J Jackson. When Jackson researched Goodman, he learned that the bandleader toured across America with his orchestra, but almost ran out of money by the time they hit California. Goodman's music was featured on a late-night radio show in New York that was also broadcast to the West Coast, where it got a lot more listeners because it was on three hours earlier thanks to the time zone difference. So when Goodman and his orchestra played Los Angeles, they drew huge crowds. This led to a residency at the Palomar Ballroom in LA, and thus began Goodman's rise to the top - he would soon become known as the "King of Swing."
"We identified with the idea of 'keep going even when it doesn't really make sense,'" Jackson said in his Songfacts interview
. "We've been independent for so long and doing this all on our own. For us, it was something we could relate to: just holding in there, hoping someone will care enough someday to take a chance on it."
Saint Motel got their big break in 2014 when they signed to Elektra Records and released the EP My Type