#2 - Carole Montgomery

Carole Montgomery is a stand-up comedian, writer, director, and producer with nearly 50 years in comedy and dozens of TV credits from the 1980s comedy boom, with her first big break coming on Showtime’s Comedy All Stars hosted by Don Rickles. After her son was born, she began a 10-year run in Las Vegas, first hired by Steve Schirripa at The Riviera and later at The Luxor. She’s performed at the Montreal Just for Laughs, Boston, and New York comedy festivals, and counts her 11 comedy tours for Armed Forces Entertainment as her proudest work. In 2017 she created Funny Women of a Certain Age, a showcase of female headliners over 50 that grew into three Showtime specials. The first, which premiered in March 2019, made history as the first TV comedy special to feature female comics over 50, and all three specials were rereleased by Comedy Dynamics in March 2025. Helen and Carole talk about how a wish made in a hotel bathroom turned into a decade-long Vegas residency, surviving the comedy condos of the ’80s (chair under the door included), and why going on last doesn’t make you a headliner. They get into viral fame versus real stage time, what it actually means to “kill,” the double standard behind asking women to “work clean,” Carole’s house rule that kids could curse only if it was funny, and the Today Show appearance that aired the weekend the world shut down for COVID. Plus: what’s next for Funny Women of a Certain Age. See Carole live: Funny Women of a Certain Age with Carole Montgomery, Kerri Louise & Tammy Pescatelli, Saturday, October 17th, 2026 at 7:30 PM at the Paramount Theatre in Middletown, NY. Tickets: https://www.ticketmaster.com/event/300064E24440979B middletownparamount Find Carole: Funny Women of a Certain Age: funnywomenofacertainage.com Instagram: @carolemontgomerycomic