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6 Smart Comedy Specials for Labor Day Weekend

August 29, 2025
in News
6 Smart Comedy Specials for Labor Day Weekend
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Ali Siddiq, ‘My Two Sons’ and ‘Rugged’

(Stream them on YouTube)

Ali Siddiq became an unlikely breakout comedian thanks to a four-part epic, “The Domino Effect,” that turned tales of the drug trade and the justice system into dynamic comic storytelling. His two follow-up specials, released this summer, provide a test: After exhausting all his childhood stories of life on the street, could Siddiq still be as entertaining talking about the more mundane subjects of a comfortable middle-aged life?

Now in his 50s, Siddiq digs into parenting, multigenerational tension, his inability to fix things around the house. Instead of describing being locked in the trunk of a car, he talks about jogging in Hoka sneakers in a gated community. This should be a letdown, and yet somehow the tension stays high, the comic twists pivot just as sharply and the stakes at least seem as dramatic. The subject matter is more conventional stand-up material, but that makes his power to playfully startle even more impressive.

Using hyperbole, swagger and consistently unusual phrasing, Siddiq can make the choice between salad and catfish on a menu seem exciting. “My Two Sons,” which bluntly contrasts the challenges of raising a rough-around-the-edges child and one with upscale manners, is the funnier, more dynamic special. “Rugged,” a fleet hour meditating on manhood, is built around his daughter’s seeing him as less than tough. There’s a bit more vulnerability in his persona here, but only a little. Siddiq is not sentimental. What makes him different is not the nature of his life, but the cleverness with which he details it.

Jim Norton, ‘Unconceivable’

(Stream it on YouTube)

“My wife’s penis,” Jim Norton says, pausing, before interrupting himself to comment on how this sentence is being received: “Which I realize sounds like the title of a progressive children’s book.” This leads to a rapid-fire series of punchlines imagining the book and its layout, then moving into jokes about being married to a transgender woman. With an absence of righteousness, he explains how her gender doesn’t define their lives at all. Her penis, he says, is the only difference from previous relationships with women. But he emphasizes: It’s still a difference. “If you think it’s humbling for your wife to make more money than you …,” he says, with the cadence of a borscht belt veteran.

A stalwart of the New York club scene, Norton understands how to take a funny idea and wring every bit of humor from it. Packed full of tight, crass jokes, this special is the work of a pro, assured in his craft, gimmick-less, pandering to no one. He finds novel takes on the “glory days of cheating” (“2007 and the 14 billion years before that”) and bandwagon sports fans. Norton has lived an interesting life, as a self-proclaimed sex addict now a proudly faithful husband who sleeps separately from his spouse. But what stands out about him here is how he discusses all of this casually, almost offhandedly. There’s a political point here, but making it explicitly wouldn’t be his style.

Beth Stelling, ‘The Landlord Special’

(Stream it on YouTube)

If you don’t have the time or interest for an hour of jokes but want more than a quick video, try this charming 28-minute release from Beth Stelling. This is not a major work by the elite comic but a very satisfying transitional one. Instead of an hour of punchlines, she tells one coherent story, filled in with laugh lines. Dressed in a casual sweatsuit, Stelling presents a theatrical portrait of her annoying landlord, who tried to raise the rent during the pandemic (or “the pandemonium,” as Stelling calls it). She approaches her subject with too much goofiness for it be a hatchet job. But it may be more brutal, because these jokes amount to a closely observed character study with the authenticity that can come only from textured scene setting. It’s a quintessentially urban special, since it draws on the peculiar obsession of imagining life from the noises overheard through apartment walls. There’s world-building here, put together from clatter upstairs and wailing down. In the process, Stelling reveals that even a tiny amount of power is ripe for abuse.

Vir Das, ‘Fool Volume’

(Stream it on Netflix)

“Just make me laugh.” One of the few moments in his latest special that Vir Das gets angry is when he describes this request. His response: “Get someone to tickle you.” It’s a nice comeback, one that hints at the artistic ambition of this talented performer. His new hour mixes jokes that are silly and serious, political and personal, with throwaway puns and involved yarns. He makes references aimed at audiences in India that Americans won’t get and vice versa. He proves that jokes translate even if you miss some of the details.

This special cuts together three very different shows, in a vast arena in Mumbai, a chapel in London and the Comedy Cellar in New York. Chris Rock pioneered this tactic in “Kill the Messenger” (2008), and the most impressive aspect of Das’s delivery is how little he changes to fit the room. That’s his most interesting subject, too: the challenge of being himself in wildly different contexts. His forthcoming book, “The Outsider,” is one of the better comedy memoirs in years, in part because he’s so articulate about straddling worlds. His movie-star charisma translates to the page but can also be a crutch. In the special, banal arguments about how people are more nuanced than they seem or how young people are obsessed with identity require either new angles or more jokes to work. Das may also try to do too much, weaving in a subplot of losing his voice six weeks before shooting the special that doesn’t really have much suspense because we know how this ends.

David Drake, ‘Big Break’

(Stream it on YouTube)

You know that cool Brooklyn guy who finally settles down, has a kid and grudgingly moves out to New Jersey, but still feels on some level like he belongs in the city? David Drake makes a comic meal out of this persona. Quietly building a prolific career of consistently funny, self-produced specials, his third one, shot in a bowling alley in Greenpoint, takes aim at his old home (“People born in Brooklyn who stay in Brooklyn are a very specific kind of hillbilly”), the absurdity of dating while married and the trauma of seeing your father’s penis (“I can remember it better than my first kiss”). Marrying a rough, likably stumbling style with honed jokes, he leans into humiliation. He wears a suit but looks uncomfortable in it. When he says he is embarrassed about revealing something — as in a hilariously awkward story of inappropriately telling a babysitter that he’s worrying about money — you believe it. “Some comics do crowd work and ask: Hey, what do you do?” he says, adding that he does that, too. “But what makes me unique is sometimes I’ll follow up four days later and see if you’re hiring.”

Jason Zinoman is a critic at large for the Culture section of The Times and writes a column about comedy.

The post 6 Smart Comedy Specials for Labor Day Weekend appeared first on New York Times.

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