Sheryl Underwood Wants to Bring Variety Shows to San Antonio—Starting This Weekend
By Leroy Adams
The comedian, TV personality, and Air Force veteran discusses the importance of community connection, why social media can't replace live performance, and bringing her "I Need a Job" tour to San Antonio.
Sheryl Underwood doesn't mince words. When she titled her current comedy tour "I Need a Job," she meant it literally—not as a punchline, but as a mission statement. The veteran comedian, best known for her decade-long run as co-host of CBS's The Talk, is adamant that live comedy isn't just entertainment; it's economic survival for performers and cultural sustenance for communities.
Joined by her touring partners Kyle Irby and Jay Lamont, Underwood brings her brand of sharp political commentary, fearless observations, and unfiltered humor to San Antonio's LOL Comedy Club this weekend for five shows across three days. But beyond the laughs, she's building something bigger: a vision for variety shows, gospel plays, and digital media platforms that put working entertainers—and working Americans—first.
In conversation with The Layover Podcast, Underwood discussed everything from the mechanics of great comedy to why she stays politically engaged despite criticism, and how communities can support live performance in an age where everyone's glued to their phones.
You're calling this the "I Need a Job" tour. That's pretty direct. What's the story behind that?
[Laughs] Everybody kept asking me in interviews why I was working so hard and why I needed all these shows. The answer is simple: I need a job. I'm no longer on daytime TV. All that other stuff people read about me—that's living in the past. I've got to make money because Kyle Irby and Jay Lamont and I have bills to pay, just like everybody else. We make more money in a short period than a lot of people, but we're not what you think we are. [Laughs] We pay mortgages, car notes, student loans. We've got the same responsibilities as everyone else.
You've got this tradition at the end of your shows where men from the audience get to walk across the stage and potentially win money. What's that about?
We celebrate guys, and there's always a question about why we're doing that. At the end of the show, we get three to five volunteers from the crowd, and they walk across the stage to music. If they can get the crowd on their side, they might win some of my money. We've been doing this since 2023. Some of these guys are great dancers, some do tributes to their ladies. We don't care about race, sexual orientation, marital status—none of that. We just want you to have some courage. Latin men, white men in your Wrangler jeans and boots- [Laughs]- get up and boogie. This is a different kind of show, and it's for everybody.
You mentioned you were in the Air Force Reserve and trained at Lackland. How does that military background show up in your work?
I was stationed at Lackland, and I have some really great stories from being in the military. We do military shout-outs in the show, and we care deeply about our troops. Right now, we're praying for the National Guard members serving in DC. People don't understand how much we really care for our military. That experience taught me discipline and gave me a different perspective on service and community, values I bring to everything I do.
You do sex and politics in your comedy—two topics people say you're not supposed to discuss. How do you navigate that, especially in today's climate?
There's nobody that does sex and politics with a street flair like me. I don't bash, I just sprinkle. I talk about my feelings and my perspective. I'm still registered Republican, and I'll tell you why in the show. But regardless of who the Commander-in-Chief is, I'm pro-American. I want all Americans working. People who've seen me on The Talk know that I'm balanced. I believe in having the conversation, not shutting people down.
Social media has changed comedy dramatically. You've got comedians building entire careers without ever stepping on a stage. What's your take on that?
I'm not against social media comics at all. In fact, I'm learning TikTok and Snapchat right now because I know that's where audiences are. But here's the thing: you can write jokes every day and post a whole set every week, but I don't believe you can polish material that fast. I like old school—Richard Pryor, Redd Foxx. If Richard Pryor didn't do Mudbone or something you recognized, you hadn't really seen him work. There's a difference between new school comedy and old school craft. What I want is for these social media comics to start producing their own movies and sitcoms, and then come get some of us that have followings too. Let's work together.
But you're clearly invested in multiple platforms yourself—podcasts, radio, potentially streaming content. How do you see all of that fitting together?
The audience is not just on social media. They're on radio, television, everywhere. That's why me, Jay, and Kyle do all radio formats—country, Latin, pop -[Laughs]- all of it. We grew up in a time when everybody was listening to everything. We know music across genres because to be a great standup comic, you should know a lot of everything. Right now, I'm producing Sheryl Underwood Radio where we contribute to stations across formats because live comedy needs to be promoted everywhere people are consuming media.
You've mentioned wanting to bring gospel plays and variety shows to communities like San Antonio. What's driving that vision?
Everything I'm producing has something to do with comedians, especially female comedians, because we need our due as well. But it's bigger than just comedy. I want to bring back the variety talent show, not just in theaters, but in comedy clubs first. We'll have singers, musicians, dancers from the community get up and perform. If you're the baddest country western singer in town and you can sell out a show, I'll let you get up and do some time. We've got to find this talent and give them platforms.
The gospel plays—Part One and Part Two—are about bringing souls to Christ while putting Americans to work. Tyler Perry gave us the blueprint. We've got enough talent: singers, dancers, set builders. We want churches, Greek letter organizations, and businesses to underwrite and sponsor this. This is for everybody. The work won't end until everybody hears the good news [Laughs].
There's a tension in what you're describing—doing adult comedy to fund faith-based projects. How do you reconcile that?
[Laughs] God knew me before I knew myself. He's given me grace, time, and blessings. I've got to go out and do something for somebody else while He's still letting me be on this earth. If you're a church person who can handle adult material at the level I'm doing it, and you want to pray that I become stronger with the Lord and be a better me, this show is for you. But if you're supper saved with your faith, wait for the gospel play. I'm working in a nightclub right now, this ain't for the family. But I've got something for the family coming.
What do you want people to understand about supporting live comedy right now?
Ticket sales are how we finance everything—the development of the gospel play, the animated projects, the podcast, the radio show. When you buy a ticket to one of our shows, you're not just getting entertainment. You're supporting a whole ecosystem of creative work and helping other performers get opportunities. Social media is exhausting, and people are shifting back to traditional media consumption. They want that live experience—the crowd, the laughter, that energy you can't get from a clip online. We need communities to show up, not just online but in person.
What advice would you give to up-and-coming comics today?
Put God first. Ask the Lord to show you the way—not your will, but His. Whatever you're going to do, put God first and He will open every door. Even when obstacles appear, ask "What am I meant to learn here?" Beyond that: study, study, study. Watch the comics you like and figure out what they're doing. Try your jokes out in conversation. Work your craft relentlessly. And remember, if guys are telling your jokes, you know you've got good mechanics—your material has legs and bones.
Sheryl Underwood's "I Need a Job" tour stops at LOL Comedy Club in San Antonio for five shows this weekend: two Friday, two Saturday, and one Sunday. Special pricing available for military members and government workers. For tickets and information, visit the club's website directly. Follow Sheryl's work on Instagram and check out her podcast, "One More Question," and "Sheryl Underwood Radio" across formats.
