Comedian’s truthful, viral stand-up comes to Lexington with a shifted edge

Whitney Cummings has always been OK with taking risks with her edgy, unfiltered comedy. Those risks have paid off over the past 20 years.

Initially breaking through as the stand-out comic at various Comedy Central Roasts, she has racked up a six stand-up comedy specials, helped co-create and co-write the popular CBS sitcom “2 Broke Girls,” launched a podcast (“Good For You”), wrote a memoir (“I’m Fine…And Other Lies” in 2017), starred in her eponymous sitcom (NBC’s “Whitney”) and hosted a game show (“Friends: The Game Show” on Max).

While Cummings said she found her comedic voice early and leaned into the raw, candid nature of her life for material, she recognizes she has to change if she wants to progress in her craft.

“Now, it’s about being vulnerable, being surprising. It’s about telling the truth. It’s about, OK, I’ve always been edgy…what’s the most surprising thing I can do?” Cummings said. “It might be…being wholesome.”

No one can mistake Cummings’ stand-up on her current “Big Baby!” tour, which comes to the Lexington Opera House this Friday, as all-ages entertainment. That being said, the wholesomeness she is referring to may come from talking about a topic she has never been able to mine for personal comedic material.

In December 2023, at age 41, Cummings welcomed her son, Henry, into the world. She said the moment changed everything, including how she approached her comedy.

“I always just want to come up very tough and show that side of myself. Having a kid, you don’t have as much to prove to anyone,” she said. “I’m no longer scared to show my feminine side, the way I used to have to hide it. I kind of feel like I’m just getting started…now that I’m a mom.”

While Cummings takes some extra considerations when crafting her brand of observational humor (“my son is going to see this some day,” she said), she is still not afraid to go out on a limb for the sake of some tense laughs.

More recently, Cummings appeared alongside co-hosts Andy Cohen and Anderson Cooper during CNN’s 2024 New Year’s Eve celebration. The moment where Cummings conducted a “Roast of 2024” soon became a viral clip after she made jokes about Kamala Harris, Hunter Biden’s laptop, Joe Biden, and Big Pharma to the visible discomfort of her co-hosts on the typically left-leaning news network.

“Going viral is always the goal, as long as it’s something you’re proud of,” she recalls. “I try to go, like, I’m not going to go on CNN and make fun of Trump. I’ve already done that. That’s the safe way. As a comic, you have to make sure you are picking your moment that is dangerous. Where there is tension.”

Cummings said the combination of aging and motherhood has given her a sense of clarity and maturity she wasn’t expecting with a self-imposed pressure to produce the best stand-up of her career, saying, “anytime I’m not spending with him, I’d better be making something great.” She said this refresh on her comedy has allowed her to appreciate when she can attract her “tribe” and maintain brutal honesty along every stop.

“To me, it’s the journey of how you can become a successful comic and not give a (expletive) if people like you. It’s a weird balance,” she said. “There’s enough people lying and pretending. I don’t need to be one of them.”

Whitney Cummings

What: Comedian Whitney Cummings: Big Baby! Tour

When: 7 p.m. May 2

Where: Lexington Opera House, 401 W Short St.

Tickets: $23-$60; Buy online at Ticketmaster.com