In 1991, Higgins was featured in Broadway's La Bête and, in 2000, he was seen Off-Broadway at Second Stage Theatre in a production of Edward Albee's Tiny Alice. He also originated the title role in Paul Rudnick's Jeffrey Off-Broadway in 1994. Higgins' numerous television credits include recurring characters on Ally McBeal, Brother's Keeper, Boston Legal and '. In Season 8 of Seinfeld, he portrayed Elaine's boyfriend Kurt. He also played attorney Wayne Jarvis in five episodes of Arrested Development. Higgins arranged the dense vocal harmonies sung by the nine-part New Main Street Singers in 2003's A Mighty Wind, a change from the writers' original concept to have the group sing in unison, leveraged by Higgins' musical talent. Higgins gained more recognition by being featured in the films Fun with Dick and Jane and The Break-Up, for which he also wrote vocal arrangements. His work as a voice actor includes the roles of Judge Mentok in Harvey Birdman, Attorney at Law, 2401 Penitent Tangent in Halo 2, and Riddler in '. Higgins also portrayed David Letterman in the HBO TV film The Late Shift. Higgins was seen in the pre-show video for the Epcot attraction Test Track. However, the ride was refurbished in 2012 and the pre-show room was removed. Higgins directs and appears on the stage from time to time as well. In 2004, he played Secretary of DefenseDonald Rumsfeld in the American premiere of David Hare's Stuff Happens at the Mark Taper Forum in Los Angeles. In 2003, he played the title role in A. R. Gurney's Big Bill at New York'sLincoln Center Theater. Higgins has been featured in TV ads for DirecTV alongside fellow co-stars Christopher Guest and Ed Begley Jr. and for Old Navy. He also stars in season 2 of TNT's Raising the Bar as an openly gay, rule-obsessed judge. Higgins took part in The Suite Life on Deck, taking the role of the obnoxious and secluded Mr. Tipton. In 2011, Higgins was cast in Happily Divorced opposite Fran Drescher. He played Fran's gay ex-husband, Peter Lovett, a character based on Drescher's real-life gay ex-husband Peter Marc Jacobson. In 2012, Higgins was cast as the voice of vain and eccentric businessman Iknik Blackstone Varrick in The Legend of Korra. From 2017 to 2018, Higgins starred as Chuck Pierce on the NBC comedy series Great News. On the syndicated game show 25 Words or Less in late 2019, Higgins told host Meredith Vieira he also goes by just "Michael Higgins" which his friends and others use a lot, and since that episode Vieira has used only that name when he's on. In 2020, Higgins began appearing in a series of adverts for 123.ie, an Irish insurance company. Higgins played the role of Principal Toddman in the 2020 Peacock comedy series Saved by the Bell which was created by Tracey Wigfield.