‘Funny Women of a Certain Age’ - times four

Milford. Comic Carole Montgomery returned to the Milford Theater for the fourth year in a row with a new show and two friends.

| 27 Jan 2026 | 02:06

Funny woman Carole Montgomery returned to the Milford Theater for the fourth year on Jan 24. This time, she brought two other comedians who were new to the trio with her: Missy Hall and Vicky Kuperman. Montgomery likes to rotate the cast to give more funny women more exposure.

Montgomery is not only a successful comedian in her own right; She is a strong advocate particularly for older women comedians, as well as being an entrepreneur for the show she created. She has three specials streaming on Showtime and thousands of followers on Instagram and Facebook.

The audience at the Milford Theater loved the group. It was a full house. One could feel the love in the audience. While many were there for the first time, there was a group of loyal followers who come year after year. These women know what to expect and the thunderous applause Montgomery received when the curtain opened was testament to that.

There were people of all ages. They responded by raising their hands when Montgomery called out an age – 40, 50, 60 – all the way up to 90. There was one woman in the audience who was 25, and the comedians, in turn, addressed her as “Hey, 25...” which became hilarious, and she was a very good sport.

There were more men this year in the audience than in years past.

“I really learned a lot,” attendee Jim Lacey said.

“Even I got many of the jokes,” Barry Schmidt added.

“We love to have men in the audience,” Montgomery said. “There’s something for everyone.”

The laughter in the audience was just about non-stop. The jokes came fast and furiously, and the comedic timing was perfect. Hall and Kuperman each had their own set and each was different in style. Montgomery pointed out that though each one is different, both are very funny. More importantly, they are all best friends which, as Montgomery said, can really make or break a show.

Milford resident Judy White said that she and her friend have a standing date to meet every year for dinner and to come to this show.

“Their humor is either cerebral or raunchy, or even both at the same time and we enjoy it all,” she said.

Montgomery said that she loves coming to the Milford Theater.

“Great audiences, good crowd,” she said, adding that she loves dealing with Beth O’Neil and the others on the theater staff.

Does Montgomery ever repeat material from year to year?

“Each year is really different and of course it almost has to be,” she said. What is the same is the quick wittedness of the jokes and the uproarious laughter.

“I had such fun at the Milford Theatre, saturated with nearly two hours of nonstop laughter. It really hit the spot!” local resident Paula Luckring said.

The take-away is that funny never gets old.