There are several ways to handle the indignities of modern life: complain to your friends, pay a therapist, or turn them into material and charge admission. The third annual Catskills Comedy Festival supplies plenty of practitioners of the last approach, gathering touring stand-ups, regional comics, and performers whose work wanders beyond the microphone. Running October 16–18, the festival spreads across seven venues within walking distance in Catskill village, making it possible to move between theaters, bars, and cafes in pursuit of your preferred flavor of funny.
Saturday’s headliner, Jared Freid, has built a career examining the gap between adult expectations and actual adult behavior. His Netflix special “37 & Single” tackled dating apps, awkward setups, and the arguments people construct to justify breaking up. His new special, “The Family Plan,” turns to vacationing with his parents and family embarrassments. As cohost of the dating podcast “U Up?” and host of “JTrain,” Freid also fields other people’s relationship problems—a renewable resource if ever there was one. He performs at the Community Theater with Tina Friml, whose comedy addresses living with cerebral palsy and other people’s assumptions about disability, and opener Alex English.
Friday begins at the Community Theater with Ophira Eisenberg hosting Jocelyn Chia and Raanan Hershberg. Eisenberg, the former host of NPR’s “Ask Me Another,” brings a storyteller’s sensibility to stand-up; Chia’s resume includes a previous career as a corporate lawyer, a profession with considerable potential for comic grievances. Later, Sean Patton performs at the same theater, with LizaBanks Campagna opening.
Across town at the Avalon Lounge, John Hill takes a more theatrical route through personal mortification. His musical solo show “Silk and Loose” begins with a viral social-media comment about his backside and spirals into questions about aging as a gay man approaching 50. Hill, whose credits include Broadway’s “Hairspray” and cohosting “Andy Cohen Live,” considers whether the life you’ve assembled resembles the one you imagined. Apparently, this accounting requires songs.
Saturday also makes room for discussing the jokes themselves. At “Crossing the Line (Can Comedy Go Too Far?),” The Moth’s Sarah Austin Jenness moderates a conversation with Hill, longtime Letterman comedy coordinator Eddie Brill, and Kingston’s Squalid Gold Comedy School founder Lauren Kincheloe. Later, Dan Madonia hosts “Local Laughs” at the Avalon, showcasing Hudson Valley and regional talent.
Sunday’s Squalid Gold Comedy School showcase at the Community Theater brings the weekend’s themes of personal mortification closer to home. Hosted by Kincheloe, the show features people with lives well beyond comedy—a chef, a veterinarian, a political theory professor—telling vulnerable, hilarious stories drawn from their own experiences. Elena Cruz, Jess Edelman, Mie Inouye, Jill Mary, Sarah Mesler, and Svetlana Chirkova take the stage. For audiences, there’s the pleasure of recognition: Your neighbors have embarrassing stories, too, and some have learned to tell them exceptionally well.
Sunday’s “Grapes of Laughs” at Chemistry Wine Bar pairs comedians’ sets with wines selected by Dori Fackler, with Eisenberg hosting Brian Balthazar and Erin Harkes. For anyone who has described a comedian as dry, this is an opportunity to investigate the tasting notes.
The Catskills Comedy Festival runs October 16–18. Individual tickets and a $70 three-event pass are available; the pass excludes the headliner and “Grapes of Laughs.”
