REAL TALK: Bill Maher
This summer, Bill Maher passed 500 episodes of his HBO show Real Time With Bill Maher. Before that, he hosted Politically Incorrect on ABC and Comedy Central dating back to 1993. That's more than a quarter century of prickly, controversial takes. Some might wonder: Isn't that maybe enough? Maher's forthright, often antagonistic style has over time earned him just as many haters as followers; controversies over everything from saying the N-word to needling fans mourning late comic book icon Stan Lee. This marks the second straight year Real Time hasn't been nominated for an Emmy; before that, Real Time and Politically Incorrect had been nominated for an Emmy almost every year since 1995. (Maher's lone Emmy win came as an executive producer for Vice in 2014.) However long his late-night shows run, Maher, 63, will always have standup to fall back on. And the fact that his Clearwater show is sold out proves there will be an audience. 7:30 p.m. Sunday. Ruth Eckerd Hall, 1111 N McMullen-Booth Road, Clearwater. (727) 791-7400. rutheckerdhall.com.
SHOCK STAR: Wendy Williams
In 2015, Wendy Williams tried something relatively new in St. Petersburg. The TV, radio and fashion mogul had been trying her hand at standup for the year, and the Mahaffey Theater marked the first stop on a 12-city tour. "I definitely think that people who only watch the TV show don't know the real me," she told the Times in an interview back then. She has had four more years to refine her act, which she now promises will deliver tea spilled from her many multimedia adventures from Harlem to Hollywood. $49.75 and up. 8 p.m. Friday. Mahaffey Theater, 400 First St. S, St. Petersburg. (727) 893-7832. themahaffey.com.
REPRESENT: Matteo Lane
"Hi, thank you so much, yes, I am gay," Matteo Lane said in 2017 upon being introduced on The Late Show With Stephen Colbert. It was just an opening line, but it was significant. Gay male comics are still relatively rare in the most prominent circles of standup, but Lane is changing that fast. He has performed on Late Night With Seth Meyers, Comedy Central's The Comedy Jam and other shows, and last year, the Advocate featured him in an issue about LGBTQ "Icons, Innovators, and Disruptors" in pop culture. "There's a long time in comedy that you fight stereotypes, until one day you just accept who you are, and say you know what? I am gay and I am proud," Lane told the magazine. "It's what separates me and makes me different." That, and he's really funny. $12 and up. 8 p.m. Thursday, 8 and 10:30 p.m. Friday, 7:30 and 10 p.m. Saturday, 7 p.m. Sunday. Tampa Improv, 1600 E Eighth Ave. (813) 864-4000. improvtampa.com.
FORWARD: The Gap and the Glue
Part of American Stage's mission is to engage the next generation of audiences and artists. To garner younger audiences, the theater offers the Under 30 Pass, a $15 monthly pass for people in their 20s. And to stimulate the next generation of artists, there is a yearlong apprenticeship program that culminates in an original work written, produced and performed by the apprentices. The Gap and the Glue opened July 31 and runs through Aug. 16. Performances are free, another way to lure younger viewers. The play imagines a future in which theater has suddenly been banned by the government. Forty minutes before the house opens for a Shakespearean festival, four actors scramble to make the show go on, their personalities clashing while losing crucial elements along the way. But they fight the powers that be, all in the name of theater. 163 Third St. N, St. Petersburg. (727) 823-7529. For showtimes, visit americanstage.org.
TOPICAL: The Hundred Dresses
Innovocative Theatre believes that theater can spark change, making a difference in the world. The 3-year-old company takes its name from mashing the words innovate and evocative, presenting thought-provoking plays and holding discussions on the topics covered. Past subjects have included dementia and abortion. Now it's bullying, with a play based on a children's book. The Hundred Dresses is geared toward grade-school kids and has a multigenerational cast. The play follows Wanda, a Polish immigrant struggling to fit in with the other kids in her classroom in 1938 during the Great Depression. A pack of mean girls torments her after she claims to have 100 beautiful dresses, although she only ever wears one. Straying from the original book, this production is told through the eyes of one of the mean girls who becomes faced with an uncomfortable choice. It opens Thursday and runs through Aug. 11, with postmatinee talkbacks with experts on select days. $15-$20. Stageworks Theater, 1120 E Kennedy Blvd., Tampa. For showtimes, visit innovocativetheatre.org.