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Roslindale Comedy
Photograph: Courtesy Roslindale Comedy/Angela Sawyer Roslindale Comedy

The best alternative comedy spots in Boston

Looking for some alt comedy? These venues host all things funny, from open mics to America’s longest-running play.

By Linda Laban

In addition to the best comedy clubs in Boston, the Hub’s underground and alternative comedy spots have something for everyone who wants to laugh. Check out an open mic night, catch illusionists who don't take themselves too seriously, or see a comedy whodunit that is recognized in the Guinness Book of Records as being the longest running play in the USA, ever. To complete an evening of fun, add in dinner at one of the best restaurants in Boston, late night drinks in the city’s best dive bars, or a visit to the city’s buzziest culinary hub, Time Out Market Boston.

RECOMMENDED: Full guide to the best things to do in Boston

Boston's best alternative comedy

Charles Playhouse
Photograph: Courtesy Yelp/Eric G.

1. Shear Madness at the Charles Playhouse

Theater Performing arts space Theater District

Hidden away beneath the Blue Man Group’s home in the main Charles Playhouse, the award-winning Shear Madness show, which opened in 1980, is recognized by the Guinness Book of World Records as the longest-running play in the USA. The comedic fun is set in a hairdressing salon, hence the title, and the story unfolds as a mystery whodunit. The show is interactive: after a murder is committed, the audience has the opportunity to find the clues, question the suspects, and solve the mystery. However, this is improv comedy theater and spontaneity keeps the mystery going, ensuring that the story, and the protagonist, changes with every performance.

Wonder Bar
Photograph: Courtesy Yelp/Nick M.

2. Thunderbar at Wonder Bar

Bars Allston/Brighton

Thunderbar is the weekly comedy open mic held at the longstanding Allston hangout, Wonder Bar. Each Thursday, before music begins later in the evening, comics and would-be comics test their skills with the audience. Hosted by Owen Linders, this is an anything-goes kind of event, and the least adventurous performers tend to be rejected by the crowd. This is the place to test your comic and crowd skills; or, on the other side of the fence, enjoy a good laugh—or a good heckling session. Feeling inspired to tell a joke? Sign up at 6pm before the show begins. The event is 21-plus.
Thursdays at 7pm

Four Handed Illusions
Photograph: Courtesy Four Handed Illusions

3. Four Handed Illusions at the Library Room

How often do you go to a comedy show in a Beacon Hill mansion? Illusionists Joel Acevedo and Steve Kradolfer mix magic and comedy during these regular performances in the historic Hampshire House’s Library Room. The room looks and feels like a private library and the audience is limited to only 50 guests, providing a uniquely intimate setting. The two-hour show includes an intermission and starts with a half-hour pre-show reception in the Hampshire House's Baker Bar, where drinks are available for purchase. Then it’s into the library for a show of supposed telepathy, precognition, and mind reading, all delivered with a sense of humor. Note: the show is 21-plus only and, in keeping with the setting, cocktail attire is encouraged.
Jan-Nov; see website for schedule

The Middle East, Music and nightlife, Boston
Photograph: Michael Young

4. The Comedy Support Group Open Mic at the Middle East

Music Music venues Central Sq

Every Tuesday night, everyone’s favorite rock club and neighborhood hangout hosts a long-running open mic comedy night, which nowadays is MC’d by Daybreak Comedy. The open mic performances take place in the Corner bar, allowing patrons the chance to grab a bite beforehand for a bohemian-style dinner and a show. The event begins at 9pm and is 18-plus. There is no cover charge.
Tuesdays at 9pm

Great Scott, Music and nightlife, Boston
Photograph: Jessica Howe

5. The Gas at Great Scott

Music Music venues Allston/Brighton

The Gas is another comedy night held in a beloved hangout that’s more associated with music. Held every Friday in the early evening, before the venue switches to rock and roll, the event is hosted by the Boston-based comedian Rob Crean, a veteran Boston comedy show producer and noted comic. Expect a comedy show featuring national and local performers, all in Great Scott’s low-key atmosphere. The Gas begins at 7pm, is 18-plus, and has a $5 cover charge.
Fridays at 7pm

Roslindale Comedy
Photograph: Courtesy Roslindale Comedy/Angela Sawyer

6. Roslindale Comedy at The Square Root

Every Wednesday night at The Square Root, a bright Roslindale Square café, this comedy show features performances from both established and emerging comics. The atmosphere is more chill and the humor less combative than many underground comedy nights; the comics are often familiar faces from the nearby Rozzie Theater. There's food, great coffee, and also wine and beer for sale. Seating for comedy night begins at 8pm; shows start at 8:15.
Wednesdays at 8pm

Bill's Bar
Photograph: Courtesy Yelp/Bill's Bar

7. Comedy Night at Bill's Bar

Bars Fenway/Kenmore

This small Lansdowne Street bar is a Boston nightlife mainstay that hosts comedy every Wednesday night. New England comics Robert Pooley and Zach Russell host the event, which often includes performances from national comedians, some of whom have appeared on late night TV shows. Sometimes, it might be local comics cracking jokes. Performances begin at 7:30pm and are followed by an open mic around 9pm. Shows can sell out and tables generally fill up quickly; seating is not guaranteed. The event is 21-plus and, generally, there is no cover charge.
Wednesdays at 7:30pm

Midway Café
Photograph: Courtesy Creative Commons/Flickr/drauh

8. Midway Or The Highway Comedy Night

Bars Dive bars Jamaica Plain

Every Sunday, laugh your socks off with this funky neighborhood bar’s array of comedians-in-residence—a.k.a. the audience. Known as one of the city’s longtime LGBTQ-friendly venues, the Midway Cafe’s comedy open mic is hosted by Angela Sawyer of Roslindale Comedy/Rozzie Theater renown. There’s no cover charge, but remember that the Midway is cash-only and 21-plus.
Sundays at 8pm

Hennessy's, Bars, Boston
Photograph: Chris Bourn

9. Bye Bye Liver Club at Hennessy’s

Bars Quincy Market

Kick off the weekend with a smile at Hennessy’s, an Irish-styled bar near Faneuil Hall. Originally a Chicago sketch-skit comedy show, Bye Bye’s Boston franchise features an all-local cast that includes MIT grads and ex-Wall Street wunderkinds. The show is 90 minutes long and the cast and crew gather in the lounge afterwards for a meet and greet. After the comedy show, stay for the live music as bands take over the stage—there’s no extra charge. Comedy begins at 8pm and is 21-plus.
Fridays at 8pm


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