Podcast Mines Life, Love and Jewishness for Laughs

Jeremy Pinsly and Dev Rogers may be from different generations but they have more in common than meets the eye. The New York-based Jewish duo — he’s 32 years old, she’s 88 — are pursuing careers in comedy and have bonded over bagels and lox while doing a weekly podcast called “The Young & The Weary.” 

The millennial bachelor and the white-haired grandmother discuss everything on the podcast — from life, relationships and humor, to sex, Judaism and smoking weed. Pinsly said he prepares topics “that have depth, that people can relate to and tie into comedy in a way that can bring Dev into the conversation for her perspective.”

 Introduced five months ago by their mutual manager, the pair instantly hit it off. 

“Dev was so sweet and in the moment and said what she was feeling,” Pinsly said. “She has a great curiosity and seemed like someone who was willing to learn [about comedy] and take risks right off the bat. I knew she was going to be fun to work with.” 

Rogers also has become Pinsly’s “surrogate Bubbe,” since his grandmothers have passed away. “Now Dev is there to fill that void,” he said. 

Rogers, a retired occupational therapist who worked for the Jewish Guild for the Blind, could always make people laugh. “When you’re told you’re funny, you develop that,” she said. She took a comedy class three years ago and has since had professional roles in “Playing With Matches,” a short film set in a nursing home, and in the Comedy Central series “Broad City,” in which she plays a neighbor in the fifth season’s second episode, airing Jan. 31.

“As long as I can be funny, it salvages life. It opens the world up.” — Dev Rogers

Pinsly landed a marketing job after college but soon realized the corporate life was not for him and gave stand-up comedy a try. “I’d known I was funny since I was a kid. From 4- or 5-years-old, I was always the free-spirited, funny kid,” he said. He’s now sharing lessons from the comedy club trenches with Rogers, giving her homework to do in each episode of the podcast. 

 Jewish themes ­— peppered with bits of Yiddish from Rogers — are frequent fodder. Pinsly has talked about telling jokes at his bar mitzvah and growing up Jewish in Nashville as “a gefilte fish out of water. We were part of a Jewish community and I had Jewish friends, but the people I associated with the most were Christian — and when I went to college even more so,” he said. 

Of Russian-Polish heritage, Pinsly wasn’t raised in a religious home. “Judaism to me is more that connection I have with my family and Jewish people. It has become increasingly important to me,” he said. “It’s a huge part of who I am.”

Rogers, whose parents came from Ukraine and initially settled in Canada, was born in Buffalo, N.Y. and has been living on Manhattan’s Upper West Side for 50 years with her non-Jewish husband, Bruce. She’s not observant but she called Judaism “a powerful ingredient” in her life. Working with Pinsly on the podcast, she feels “automatically comfortable, it’s like mishpachah [family],” she said. “It’s a connection that’s unexpected and rewarding.”

In Episode 5 of the podcast, Pinsly and Rogers discuss “The Marvelous Mrs. Maisel,” the award-winning Amazon Video show they both love. “In a sense, I feel that she’s a role model for me,” Rogers said of the title character, Midge, a Jewish comedian. “We’re definitely going to keep Jewish themes throughout,” Pinsly said. “Maybe we’ll have a Hanukkah episode or a Passover seder.”

They’re planning to add listener questions and guests to the podcast, including filmmakers Ferne Pearlstein (“The Last Laugh”) and Lisa D’Apolito (”Love, Gilda”), and comedian Greer Barnes, who is black and Jewish. Their target audience is 25–60 years old, but not exclusively Jewish.

“We have Jewish themes because that’s a huge part of who we are, but this show isn’t just for Jews,” Pinsly said. “We want to highlight our Judaism without pushing it down people’s throats.”

Outside of the podcast, Rogers said she’d love to appear in a play, and she’s working with Pinsly on a solo five-minute stand-up routine. “As long as I can be funny, it salvages life,” she said. “It opens the world up.”

Pinsly’s short-term goal is to audition for the Just For Laughs comedy festival in Montreal; longer term, he would like to get a slot on the Jimmy Fallon or Stephen Colbert late-night shows, and also have his own stand-up special online. “I want to take my comedy to the highest level,” he said. A drummer who has played in bands, he’d also like to form “a jam band with a rock focus.”

For now, Pinsly said, he and Rogers enjoy “hanging out and having conversations and learning from each other.”

“Dev’s really good at holding up a mirror to you,” he said, noting that she has helped him adopt a more mature attitude toward relationships. “I have started dating with more intent, thinking about the value of building something more substantial. I’m currently dating a Jewish girl.”

Rogers, who has lived through breast cancer and three joint replacements, has taught her young partner by example.

“There’s no reason to stop trying, and it’s never too late to start something,” Pinsly said. “If you let all your fear go and just trust yourself, it will all work out. Pursue your dreams.”

“The Young & The Weary” is available via iTunes, Spotify, Stitcher and theyoungandtheweary.com.