Drummer/vocalist Matt Caskitt was born in Murphy, TX, leter living in Dallas, Chicago, and Denver. The first concert he attended was Pearl Jam/Bad Religion at Red Rocks Amphitheater in Colorado, which he later described as "An event that changed my life." Caskitt moved to San Diego in 2004 with a hardcore screamo band, going on to play in a couple of local bands before deciding to start his own group.

Formed in Autumn 2012 and based in North Park, the original lineup of his pop-punk band Caskitt featured his former bandmate from a shortlived metal group, El Centro's Steffen Long (guitar and vocals), alongside Riverside bassist Ricky Schmidt (ex-Beside Myself), who was later replaced by Jesse Hernandez (New Way On, Old Rivals).

Their 2013 six-song EP Don't Tell Anyone was recorded at Earthbound Recordings in Chula Vista with Chris Hopkins. Their first full album was released in April 2015, This Machine Kills Sadness. "The title obviously comes from tweaking a very famous Woody Guthrie quote he would write on his acoustic guitar, 'this machine kills fascists,'" according to Caskitt.

"About a year ago, I scribed 'this machine kills sadness' on my bass drum head, not only as a nod to Woody Guthrie but as a reminder to myself that this machine - music - has healing capabilities and is always something I can turn to when things aren't sunny. The lyrics in the title track are actually some of my favorite famous song titles constructed together, with notable nods to Bruce Springsteen, Roy Orbison, Jackson Browne, etc."

In early 2016, Caskitt and his wife Christy relocated to Hollywood, announcing that was where the band would now be based, with Caskitt in West Hollywood, Steffen Long in Oceanside, and Jesse Hernandez in Ontario CA. By the end of the year, Caskitt had moved back to San Diego.

The second Caskitt full-length Old Fires New Frontier, produced by Nick Mac and available on vinyl, was released in September 2016.