Comedian Derek Gaines Brings His High-Energy Standup to Oak Park’s Comedy Plex This November

Comedian Derek Gaines, known for his sharp delivery and upbeat, unfiltered stage presence, is set to perform at the Comedy Plex Comedy Club in Oak Park on November 28 from 8:00 PM to 9:30 PM. The show will take place at 1128 Lake Street, Oak Park, IL 60301, making it an easy spot to reach for anyone in or around the Chicago area. Fans can grab their tickets through the Comedy Plex website at this link.

Gaines made his standup television debut back in 2014 on AXS TV’s Gotham Comedy Live, a milestone that helped push him into the national spotlight. That same year, he was selected by Just For Laughs, one of the world’s most respected comedy festivals, which has showcased countless major comedic talents. Since then, Derek has steadily built a résumé that blends acting, standup, writing, and unscripted comedy.

On television, he has appeared as a contributor on VH1’s Morning Buzz and truTV’s Greatest Ever, adding comedic commentary to fast-paced entertainment formats. Gaines also had a role in Morgan Spurlock’s docuseries Connected, giving viewers a more personal look at his experiences and perspective. His comedic instincts landed him on MTV shows such as Joking Off and Broke A$$ Game Show, where his quick, spontaneous humor was central to the format.

One of his most recognizable acting roles is Jaybird in Tracy Morgan’s TBS comedy series The Last O.G., which helped introduce him to an even wider audience. Gaines also starred opposite Jane Lynch in the NBC comedy pilot Relatively Happy, showing his range beyond strictly standup-based appearances. Before that, he had a notable dramatic performance on ABC’s Training Day, proving he’s not limited to comedy alone. He later enjoyed a breakout moment with an appearance on NBC’s long-running hit Will & Grace, adding another major network credit to his career.

In recent years, Derek has continued to broaden his career, including a role in The King of Staten Island (2020) and earning industry respect for his writing. His body of work includes recognition such as a WGA Award and a Daytime Emmy nomination, achievements that highlight his versatility and commitment to his craft. More background on Derek can be found on his IMDb page at this link.

For those planning to attend the Oak Park show, the venue has a few specifics worth noting. There is a 2-drink minimum per person, which is standard for many comedy clubs. Parking is made relatively simple thanks to the Holley Court Garage, located conveniently next to the club, offering cheap parking for attendees. The Comedy Plex also welcomes outside food, giving guests flexibility if they want to bring something along before the show kicks off.

Whether you’re a long-time fan or just curious to catch a fast-rising comedian with a growing list of accomplishments, Derek Gaines’ upcoming Oak Park performance offers a chance to see a high-energy, television-tested, and genuinely funny performer in an intimate setting. If you’re in the area and enjoy live comedy, this show should definitely be on your list of things to do.