Larry and His Flask is a self-styled "Post-American rock band from Bend", a city on the Deschutes River in Oregon. They have supported several bands such as Frank Turner, Dropkick Murphys, Streetlight Manifesto, Strung Out, The Reverend Peyton's Big Damn Band and Trampled By Turtles, as well as embarking on full Canadian and American tours by themselves. Since shifting to acoustic instruments, busking has also been a part of their tours. As the group stated in an interview, "We play a lot of street corners if we are low on gas money."
They have played at various festivals; the largest to date being the 2011 Vans Warped Tour, with Alternative Press putting them on their 10 Must See Under-The-Radar Warped Tour Acts list.