Damon Williams

City Winery Chicago Presents Damon Williams live on Monday, November 23rd at 7:30 PM! Damon Williams is bringing his sharp wit and legendary Chicago style to City Winery Chicago on Monday, November 23rd for a night of nonstop laughs and real-life comedy. Join us for an evening that blends seasoned stand-up, cultural insight, and the kind of humor that has made Damon a household name for decades. With more than 25 years in the comedy industry, Damon’s journey began right here in Chicago at the iconic All Jokes Aside Comedy Club. Since then, his career has taken him to major stages and screens across the country, including BET’s Comic View, where he also filmed his own one-hour special, as well as Comedy Central’s Premium Blend, HBO’s Bad Boys of Comedy, BET Live, and TV One’s Tom Joyner Sky Show. Beyond the spotlight, Damon continues to shape the comedy scene as a manager at Riddles Comedy Club, creating opportunities for both rising and veteran comedians. Fans also recognize him from his time holding the “Funny Chair” on the nationally syndicated Tom Joyner Morning Show and his regular appearances on Windy City Live. Most recently, he stars in Laugh Tonight with Damon Williams, now streaming on UrbanFlixTV. Doors open at 6:00 PM, giving you time to enjoy City Winery Chicago’s signature wine, dining, and intimate performance setting before the show begins. Secure your seats now and get ready for a Thursday night filled with laughter, heart, and classic Chicago comedy.