Everything's Funny With Helen Keaney

#3 - Missy Hall

Helen Keaney, Jeremy Boguslaw — Mon, 19 Oct 2026 05:00:00 -0400

Missy Hall is a stand-up comedian, speaker, actress, and breast cancer survivor from Delaware, known as the “Queen of Happy Things.” She didn’t start stand-up until her mid-40s, while she was also teaching middle school. Her first stand-up performance was a one-woman show recorded live, released as the album Miss Representation, and it made the Grammy entry list for Best Comedy Album. Her albums since include Fifty Shades of Fifty, which has more than a quarter million streams, and Scoot Up, which plays on SiriusXM. She was named to Best of the Fest at the 2019 Burbank Comedy Festival, was a finalist at the 2018 Big Sky Comedy Festival, and tours with Funny Women of a Certain Age and Ladies of Laughter.

Helen and Missy met on a river cruise in Germany where neither of them wanted to talk shop, and within minutes they found out they had almost everything in common. They talk about using happiness as a coping mechanism, starting over in a house with no kitchen, and being married three times, plus the Social Security clerk who heckled Missy about it. They also get into why surprise-party comedy gigs never work, how Missy books her shows through gig sites, and life near Joe Biden in Delaware. And finally, the story behind “Holy sh*t, Helen.”

Find Missy:
Website, tour dates & newsletter: missyhallcomedy.com
Hallway Chats, every Tuesday at 8pm ET on Facebook Live: Missy Hall Comedy
YouTube: Missy Hall Comedy

#2 - Carole Montgomery

Helen Keaney, Jeremy Boguslaw — Mon, 12 Oct 2026 05:00:00 -0400

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

#1 - Cathy Ladman

Helen Keaney, Jeremy Boguslaw — Sun, 04 Oct 2026 23:47:55 -0400

What happens when two comedians who have watched the comedy business transform over decades sit down and compare notes?

Helen Keaney welcomes award-winning comedian, writer, actress and comedy coach Cathy Ladman for a candid, funny and occasionally serious conversation about stand-up comedy, show business and what it takes to build a career that lasts.

Cathy’s career spans more than four decades across stand-up, television writing and acting. She has made 10 appearances on The Tonight Show and won the American Comedy Award for Best Female Stand-Up Comic; written for hit television series including Roseanne and Caroline in the City; and appeared as an actress in shows such as Curb Your Enthusiasm, Modern Family and Mad Men.

But this episode goes well beyond the credits.

Helen and Cathy dig into how stand-up has changed in the age of TikTok, social media and follower counts, and whether popularity is beginning to overshadow the actual craft of comedy. They talk about women in stand-up, aging onstage, career pivots, motherhood, comedy clubs versus theaters, working clean, finding your authentic comedic voice and why great joke writing often comes down to rewriting, specificity and making the material unmistakably your own.

Cathy also shares hard-earned advice for newer comedians about developing original material, focusing on the work instead of comparing yourself to everyone around you, and navigating a comedy industry that looks very different from the one she entered decades ago.

It’s an insightful conversation between two longtime comedians about stand-up comedy, women in comedy, joke writing, show business, career longevity and staying funny while the industry changes around you.