Rolling Stone dubbed the program (which saw Jamieson teamed with radio personality Eddie Trunk and comedian Jim Florentine) one of the "50 Best Reasons to Watch TV".

Jamieson also co-hosted Beer Money, a fast-paced, non-traditional sports quiz show airing on SportsNet New York.

He is also a joke writer for comedian Lisa Lampanelli, and spent many years as Andrew Dice Clay's opening act.

[5] Beginning in 2019, Jamieson hosts his own weekly internet show, That Jamieson Show, which is part of Compound Media (a paid-subscription platform created by Anthony Cumia),[6] and features interviews with renowned rockers (Joe Satriani, Steel Panther, Myles Kennedy), comedians (Florentine, Joe Bartnick), plus authors and/or radio personalities (Katherine Turman, Keith Roth, Greg Prato).

In 2020, Jamieson issued his fourth comedy CD, Denim and Laughter, and planned to tour Europe with Biff Byford of Saxon, which was ultimately cancelled due to the COVID-19 pandemic.