Entertainment

Ha Ha! 12 must-see comedy shows coming to Greater Boston in summer 2023

Sitcom stars, local luminaries, and SNL regulars past and present all hit local stages this June through August.

Kevin James, Devon Walker, Ali Wong, and Leslie Jones are all headed here this summer. AP Photo/Sony Pictures, Richard Cartwright; Saturday Night Live/NBC; Joyce Kim/The New York Times; Ethan Miller/Getty Images

By Peter Chianca

8 minutes to read

The summer season is heating up — with hot comedy! (See what we did there?) Big names, local favorites, and several live-from-New-York stalwarts are all making their way to Greater Boston. It’s almost impossible to narrow them down, but here are a dozen buzzy stand-up sets, improv shows, and live readings worth checking out at local venues over the next three months. (Note: All prices listed are face value; for some shows only verified resale tickets may be available.)

Rachel Bloom. Nino Muñoz/The CW

Rachel Bloom at Crystal Ballroom 

Fans of CW’s off-kilter musical sitcom “Crazy Ex-Girlfriend” will no doubt be delighted to see its creator and star, Rachel Bloom, hitting the road with her stand-up comedy tour, “Death, Let Me Do My Special.” Never one to shy away from sticky psychological topics, Bloom straddles the line between comedy and tragedy with her post-pandemic material, notably grappling with losing her “Ex-Girlfriend” collaborator, Fountains of Wayne’s Adam Schlesinger, to COVID in 2020. But don’t worry, she’ll have her usual silly songs and neurotic observations in tow as well — and possibly a few choice words in support of the striking entertainment writers, of which she is one, in their battle against AI-written scripts. (Artificial intelligence will “be a good writer when they have the pain and trauma of hating themselves,” she told The Guardian.) Wednesday, June 7, 8 p.m., Crystal Ballroom, 55 Davis Square, Somerville, $45

Alison Leiby at Arts at the Armory

Abortion is not one of those topics generally considered, well, funny — but it can be. Cecily Strong proved it with her brilliant “Saturday Night Live” segment “Goober the Clown on Abortion,” and comedian and TV writer Alison Leiby is proving it nightly with her one-woman show, “Oh God, A Show About Abortion.” It’s not only about abortion — she also touches on plenty of other challenges facing modern womanhood and her own messy life — but its centerpiece is Leiby’s own experience with the procedure, and that fact that she didn’t particularly struggle with the decision to have it. “The more we talk about it openly and honestly, the less of a catastrophe it is,” she tells her audience, including the one in attendance the day it became clear that Roe v. Wade was being overturned. “The show is exactly the same, you know, as it was before we lost all our rights,” she told that crowd, according to Vogue. Thursday, June 8, 7:30 p.m., Arts at the Armory, 191 Highland Ave., Somerville, $27

Tina Fey and Amy Poehler. Art Streiber/NBC

Tina Fey and Amy Pohler at MGM Music Hall

If you’re one of those people who wished this duo’s stints hosting the Golden Globes would never end — we know who we are — then have they got a show for you. Taking a cue from fellow comedy legends Steve Martin and Martin Short, former “Saturday Night Live” stars Fey and Poehler (a Massachusetts native, as you probably know) start off their “Restless Leg” show with a clip reel of their greatest hits, and never looks back. You can expect improv (appropriate given the pair met at The Second City In Chicago, lo those many years ago), a revival of their turn as SNL “Weekend Update” anchors, at least one musical number, and even a Q&A. Friday, June 9, 7 p.m. and 10 p.m., MGM Music Hall, 2 Lansdowne St., $236

Kevin James at The Wilbur

OK, so maybe “The King of Queens” isn’t remembered as one of the great all-time sitcoms. But we’ll go out on a limb and say it’s actually highly underrated: As “Honeymooners”-style couples-based comedies go, it had more than its share of belly laughs over its nine seasons. Plus, Jerry Stiller! Of course, the late Mr. Stiller won’t be in attendance during Kevin James’ stand-up stint at The Wilbur, but we’re fairly confident that the erstwhile Paul Blart, Mall Cop will hold his own with his relatable (and mostly family-friendly) stories of being an annoyed plus-sized dude in America. Saturday-Sunday, June 10-11, 7 p.m., The Wilbur, 246 Tremont St., $75-$302

Leslie Jones at The Wilbur

How do we love Leslie Jones? Let us count the ways: As a towering presence on “Saturday Night Live”; as the best Olympics commentator ever; as a slam-bang “Daily Show” guest host; she was even good in that all-women “Ghostbusters” reboot. And now she’ll be bringing her raucous comedy chops to two shows at the Wilbur, where we’re pretty confident no topic will be off limits. (If you’re looking for somewhere to bring the kids, better stick with Kevin James.) You can also probably expect some of the unfiltered personal stories that make up her upcoming memoir, “Leslie F*cking Jones,” which is billed as a “love letter to regular people.” Thursday, June 15, 7:30 and 10 p.m., The Wilbur, 246 Tremont St., $39-$312.25

Devon Walker at Laugh Boston

Devon Walker might not be at the point where he’s getting regularly recognized for his “Saturday Night Live” sketches — yet. But the recently added featured player on everyone’s favorite long-running sketch comedy show seemed to just be getting into a groove (for instance as a visibly uncomfortable actor pitching HIV medication) when SNL went on a writers-strike hiatus that scuttled the end of the season. Fortunately you can catch him live and in person when he brings his standup act to Laugh Boston for three shows; no word whether he’ll revive his professional-athletes-in-quarantine bit from during the pandemic, but we can only hope. Friday, June 23, 7 p.m., Saturday, June 24, 7 & 10 p.m., Laugh Boston, 225 Summer St., $33

Brian Glowacki at The Wilbur

Maybe it was growing up on an island that nurtured Brian Glowacki’s single-minded dedication to the craft of comedy. Whatever it was, no one can deny the Nantucket native’s devotion to stand-up, a drive that led him last year to become the first independent, local comedian to headline at The Wilbur. And now he’s back, bringing his self-deprecating, larger-than-life charm — he likes to describe himself as “aggressively likable” — to the Wilbur stage once again. “I chased this thing with every ounce of my energy, and I feel like this is a moment for anyone who wants to do something big,” Glowacki told Vanyaland prior to making his mark on The Wilbur last year. “It might sound corny, but it’s less about me and more about all of us.” And you can make it about you by checking out the gentle giant when he returns there this summer. Saturday, June 24, 7 p.m., The Wilbur, 246 Tremont St., $32

Ali Wong at MGM Music Hall

It’s been a while since Ali Wong started taking over Netflix with her comedy specials, starting with the widely successful “Baby Cobra” in 2016 — famously filmed while she was seven months pregnant — followed by “Hard Knock Wife” (2018), and “Don Wong” (2022). But she hasn’t slowed down in her efforts to deliver unfiltered, personal comedy that doesn’t shy away from the topics of sex, bodily functions, and the painful vagaries of marriage. Of course, now that she’s a hard knock ex-wife (she and husband Justin Hakuta divorced last year), she may have a more nuanced (although no doubt equally hilarious) perspective to share. Friday, July 28, 8 p.m., MGM Music Hall at Fenway, 2 Lansdowne St., Boston, $46.75 – $247.

David Sedaris. Courtesy Photo / Ingrid Christie

David Sedaris at Plymouth Memorial Hall

OK, so David Sedaris might be a “humorist” rather than a comedian … but no matter what you call him, he sure is funny. Not in a “didja-hear-the-one-about” kind of way, but rather in a wry, often absurdist, and always relatable style that readers have fallen in love with over the years. And it translates surprisingly well from the printed page — where he’s been entertaining readers ever since he wrote of being a Macy’s elf in his breakthrough 1992 essay “Santaland Diaries” — to the stage. This time around he’ll be reading from his latest collection of semi-autobiographical essays, last year’s “Happy-Go-Lucky,” and as always taking questions from the audience. (Someone please ask him if his sister Amy will be getting a spinoff from “The Mandalorian.”) Sunday, July 30, Plymouth Memorial Hall, 83 Court St., Plymouth, $52-$72

Punkie Johnson at Laugh Boston 

Punkie Johnson may have discovered the secret to comedic success: Become a bartender at the Comedy Store. During her time at the famous Los Angeles comedy club, Johnson was able to observe a whole lot of what to do, and what not to do — which ultimately led to a productive standup career of her own, and eventually to getting hired at “Saturday Night Live,” where she became a featured performer in 2020. Probably best known for her “Weekend Update” appearances — including a memorable segment with Mikey Day sending up her 100% real celebrity name malapropisms (Rick Bernstein, anyone?) — she could well be on her way to SNL superstar status. Friday-Saturday, Aug. 18-19, Laugh Boston, 425 Summer St, Boston, $33

Felipe Esparza. JC Olivera/Getty Images

Felipe Esparza at The Wilbur

If you’ve seen Felipe Esparza during any of his guest co-host appearances on Cartoon Network’s totally bonkers talk show parody “The Eric Andre Show” — where he’ll be permanent co-host next season —  you know there’s very little the Mexican-American comedian won’t do for a laugh, no matter how twisted or cynical it may be. (Getting deported twice as a kid probably helped to fuel his anything-goes attitude.) Now the prolific standup — he won “Last Comic Standing” in 2010  — and host of the “What’s Up Fool?” podcast is back on the road, bringing his darkly comic takes on bad parenting, drug addiction, broken homes and other cheery topics along with him. Saturday, Aug. 19, 7 p.m. The Wilbur, 246 Tremont St., $35-$65

Ben Schwartz & Friends at Chevalier Theatre

It’s hard to pick a favorite supporting character in “Parks & Recreation,” but there’s no universe in which Ben Schwartz’s Jean Ralphio isn’t near the top of the list. But Schwartz also happens to be one of the hardest working men in comedy, appearing on numerous other TV shows — for instance in the criminally underrated “Space Force,” where the aforementioned Punkie Johnson also turned up — in movies (he’s Sonic the Hedgehog!), and perfecting one of the most engaging improv shows going. That’s what you’ll see if you check out Schwartz and his aforementioned friends in Medford, but make sure to bring your funny bone: “The audience at Ben Schwartz & Friends is laughing almost continuously throughout the show,” wrote Leila Jordan in Paste Magazine. “There isn’t a time for a joke and a time for reaction; it’s all just one experience.” Sunday, Aug. 27, 7 p.m., Chevalier Theatre, 30 Forest St., Medford, $49.50-$99.50

Ben Schwartz. The Washington Post / Carmen Chan

More comedy of note:

Reader suggestions:

Here are some upcoming shows recommended by readers after our initial publication:

  • Joe Avati, Friday, June 23, Regent Theatre, Arlington (recommended by Gtrain, Nahant)
  • Roslindale Queer Comedy Night, Friday, June 23 and Friday, July 31, The Rozzie Square Theatre (recommended by Bea, Cambridge: “Best show in the area and I love the host!”)
  • Aaron Weber, Friday-Saturday, Aug. 25-26, Laugh Boston (recommended by Bill L., Brookline)

Profile image for Peter Chianca

Peter Chianca

General Assignment Editor

Peter Chianca, Boston.com’s general assignment editor since 2019, is a longtime news editor, columnist, and music writer in the Greater Boston area.

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