While performing at more than 100 schools during the 2007-2008 school year, the Idaho native also made forays into television, landing spots on Comedy Central, The Tonight Show, and Last Comic Standing. Cummins' profile continued to build as he released his debut album, Revenge Is Near, in 2009.

After the 2010 Comedy Central special Crazy with a Capital F aired, he toured heavily, appearing at the Aspen Comedy Festival, Montreal Comedy Festival, and the 2011 Nando's Comedy Festival in South Africa. After snagging a weekly slot on Sirius XM's Naked and Fearless show on Blue Collar Radio, Cummins recorded a live set at Portland, Oregon's Helium Comedy Club, which was released in 2012 as Hear This! That year, he also joined the cast of TruTV's World's Dumbest..., and in 2013 began to find work as a consulting producer on a number of cable reality shows, such as Duck Dynasty and Porter Ridge.

In 2015, Cummins released the 30-minute standup album Chinese Affection, and Splattered Ink Press published his picture book for adults, Daddy Bear: Three Rabbits Meet the Real World. He also began an over 200-episode run as host of the talk show The Playboy Morning Show and wrote multiple episodes for the 2016 Family Channel sitcom Raising Expectations, which starred Molly Ringwald and Jason Priestley. Continuing to tour with his standup act, he released his fifth comedy album, Don't Wake the Bear, in September 2016. It captured over an hour of material from shows at The Depot in Salt Lake City the previous year. ~ Andrew Leahey & Marcy Donelson