Known for his fast-paced style and clever punchlines, Jim is a regular headliner at top comedy clubs across the country, including Zanies and the Improv, as well as being a regular performer at Brad Garrett’s Comedy Club in Las Vegas. Jim has opened for some of the biggest names in the comedy world, including Sebastian Maniscalco, Brad Garrett and Demetri Martin. In 2023, Flannigan filmed a set for Nate Bargatze's new Nateland Entertainment, to go along with several TV appearances on ABC, WGN, NBC Sports, IFC Network and more.