New York City’s comedy scene is experiencing a vibrant surge this August, with a flurry of events and performances that highlight both the city’s grassroots humor and its big-stage spectacles. From free weekly showcases featuring up-and-coming comics, to Broadway debuts by legendary roastmasters, and special appearances by internationally touring comedians, there’s no shortage of laughter to be found in the Big Apple and beyond.
Among the most buzzed-about recurring events is “We Have Fun: A Free Weekly Stand-up Comedy Show,” which has been named one of the “best free comedy shows” by Time Out New York. Set for Wednesday, August 20, 2025, at 7:30 PM (with doors opening at 7:15 PM), this show is a testament to the city’s enduring love affair with stand-up. Hosted by Zach Sims (Comedy Central, Sirius XM) and Dan Wilbur (How Not To Read, The Onion), the event boasts a rotating lineup of comedians who’ve graced the stages of The Late Show, Conan, Comedy Central, and more.
This week’s roster is no exception to the show’s reputation for quality. Audiences can look forward to sets from Yemi Afolabi (Comedy Central), Hyde Healy (American High), Maria Heinegg (HBO, Sirius XM), and Erin Depke (Limestone Comedy Fest). As always, the show is free, and the lineup is subject to change—an exciting prospect for those who love a good surprise. The event, as reported by Patch on August 16, 2025, continues to attract crowds with its accessible, high-caliber comedy, drawing both locals and visitors eager to catch the next big thing in stand-up without spending a dime.
But NYC’s comedy fever isn’t confined to club basements and intimate backrooms. On Broadway, Jeff Ross—known to many as Comedy Central’s “Roastmaster General”—is making waves with his solo show, “Take a Banana for the Ride.” The production, reviewed by NYTG on August 18, 2025, marks a new chapter for Ross, whose career has long been defined by razor-sharp insult comedy and a penchant for pushing boundaries. The show’s opening nods to his notorious roasts—think Sandra Bernhard and Bea Arthur—but quickly pivots to something more heartfelt and introspective.
Ross’s performance is surprisingly tender, weaving together stories about his upbringing, the loss of both parents in his teens (his mother to leukemia complications at 14, his father to a brain aneurysm five years later), and the formative years he spent working in his family’s catering business. The show’s title is a touching tribute to his grandfather, who would always hand him a banana before a bus trip—a simple gesture that, for Ross, became a metaphor for life’s journey and the importance of being prepared for whatever comes next.
“Take a Banana for the Ride” doesn’t shy away from the darker chapters of Ross’s life. He reads letters from his late parents, reflecting on their love for each other and the resilience that humor can offer in the face of grief. He also opens up about his recent battle with colon cancer and the pain of losing close friends Norm Macdonald, Bob Saget, and Gilbert Gottfried. Yet, even as he addresses these heavy topics, Ross maintains the buoyant, mischievous energy that’s made him a comedy staple. The show features musical accompaniment from pianist Asher Denburg and violist Felix Herbst, adding a cabaret-like intimacy that’s rare for a Broadway house.
Audience reactions have been largely positive, with a 77% approval rating compiled from 32 reviews on Show-Score. One attendee noted, “Jeff Ross roasts a little, but mostly tells emotional family stories engulfed in jokes. This is both great, but as it is a one-note rollercoaster, at times minor [sic] tedious.” Another reviewer remarked, “Jeff Ross is funny, emotional, and vulnerable as his one man show takes the audience through his life with the loss of friends and family. See it if you want a pleasant surprising funny evening with a roast master and bananas.”
Ross’s show stands out not just for its humor, but for its willingness to explore the cathartic power of laughter in the face of adversity. As NYTG observes, “After all these years of material that verges on heinous, Ross is a softie, his brand of insult jokes derived from a love of people and the world around him—even if it’s hard to see—and a desire to see people surprised.” The production may not reinvent the solo show format, but it offers a moving glimpse into the man behind the roast, inviting audiences to laugh, reflect, and maybe even shed a tear.
Not to be outdone, the comedy circuit is also welcoming a special event featuring Michael Blaustein, an internationally touring headliner, actor, and award-winning writer. Scheduled for August 30, 2025, from 9:30 PM to 11:00 PM, Blaustein’s appearance is generating considerable excitement. As reported by Awesome Alpharetta on August 18, 2025, Blaustein is known for co-hosting the hit podcast “Stiff Socks” with Trevor Wallace—a show that consistently ranks in the top 50 of all comedy podcasts on iTunes and Spotify.
Blaustein’s resume is as eclectic as it is impressive. He’s performed at over 200 colleges worldwide and appeared at major festivals like JFL 42 and the New York Comedy Festival. Television audiences may recognize him from Amazon Prime’s original series “Inside Jokes” or CBS’s “Person of Interest.” He’s also hosted two MTV pilots, was a cast member on the final season of MTV’s “Punk’d,” and even developed a Snapchat show for Comedy Central. His creative chops were further recognized when he became a comedy pilot finalist at The Austin Film Festival, and he’s credited as co-writer, co-director, and co-star of the feature film “Up There.”
For fans of stand-up, Blaustein’s upcoming show promises a blend of sharp wit, observational humor, and the kind of energetic stage presence that’s won him accolades across multiple mediums. His ability to connect with audiences—whether in a packed college auditorium or through the intimacy of a podcast—underscores the evolving nature of comedy in the digital age.
Taken together, these events highlight the remarkable diversity and resilience of the comedy world in 2025. From the raw vulnerability of Jeff Ross’s Broadway debut, to the grassroots energy of “We Have Fun,” and the multimedia savvy of Michael Blaustein, it’s clear that laughter remains a powerful force for connection and healing. As audiences gather—whether in a cozy club, a grand theater, or online—they’re reminded that, no matter the circumstances, comedy continues to offer both escape and insight, one punchline at a time.
