In 1984, Upton performed for the first time at an open-mic at the Comedy Underground in Seattle.[6] After seeing his performance, comedy promoter Laura Crocker invited him to compete in the Seattle International Comedy Competition.[6] Although he did not win the competition, he quit working as a schoolteacher two years later to pursue comedy full time.[6]
Over the course of his career, Upton has performed over 6,000 shows worldwide.[6] He is a previous winner of the Las Vegas Comedy Festival.[7][1] He was an opening comedian for Johnny Mathis from 2008 until Mathis' retirement from touring in 2025.[7][8][9] He has also opened for the late comedian Joan Rivers.[10][11][12] Upton has been seen in concert with Smokey Robinson, Kenny Rogers, Dolly Parton, Glen Campbell, and Pam Tillis.[5][10] Upton has also performed at the MGM in Macau, in Israel in 2014 as part of the Comedy for Koby Mandell Foundation benefit.[12][13]
In June 2018, a video clip of Upton's stand-up produced by Dry Bar Comedy was posted online. It became a viral video and reached 36 million views in ten days.[14] He made his Grand Ole Opry debut in 2019.[5]
Upton performed on an episode of the CBS talk show The Talk, which aired on May 17, 2024.[15] He also performed at Caesar's Palace as part of the HBO Comedy Festival.[7][16]
From 1980 to 1986, Upton was a track coach for Pasco High School.[1]
Upton volunteered as an assistant track coach at the University of Washington from 1988 to 1994, and a full-time assistant coach from 1994 to 1997.[1] From 2007 to 2022, Upton was the hurdles coach for Shorecrest High School’s track and field team.[17] While coaching for the Washington Huskies, he placed athletes in the NCAA finals and US Olympic Trials.[18]
