Carole Montgomery racked up dozens of TV credits as a stand-up comedian during the 1980s comedy boom, with her first big break coming on Showtime’s Comedy All Stars hosted by Don Rickles. After giving birth to her only child, she began a 10-year stint in Las Vegas, initially hired by Steve Schirripa at The Riviera, then eventually over at The Luxor. After returning to New York City in 2006, she performed on Nick at Nite’s The Search for the Funniest Mom in America, Comics Unleashed with Byron Allen, and on the TV Guide Network’s Standup in Stilettos. But at 48, she couldn’t find regular work in the clubs. So she started her own showcase, Funny Women of a Certain Age. It quickly became a fixture back on Showtime, with stand-up showcases airing on the premium cable network in 2019, 2020 and again in 2021. Fran Drescher, who appeared on that first showcase, is now president of the SAG-AFTRA actors union. Her third showcase features actress Teri Hatcher, plus performances by Wendy Liebman, Monique Marvez, Leighann Lord, Marsha Warfield and Montgomery herself — she joined me to share her firsthand perspective as a funny woman of a certain age.

If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!