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Comedy Shows in Boston – May-June 2023

“I would have been a lot better off if I’d studied more when I was growing up, y’know. But you know where it all went wrong was the day they started the spelling bee. Because up until that day, I was an idiot, but nobody else knew.” – Brian Regan

In June, you can catch Brian Regan live and on stage at Cape Cod Melody Tent. But he’s just one on a long list of funny people with comedy shows in Boston during May and June 2023.

Jump to:

Boston Comedy Shows May-June Highlight Reel

Stand Out Stand Ups

Boston Comedy Clubs

May-June Comedy Shows in Boston – the Highlight Reel

Note: These are taken from the official Boston Events Calendar by Evvnt hosted here on OTL City Guides.

A Round of Applause for Boston Seat Fillers

If you live in the Boston (and greater New England) area and love comedy (and other live shows!), be sure to check out OTL Seat Fillers. Seat Fillers have been in Boston for eight years, attending theatre, comedy, and special events. Low membership dues cover 2 or 4 tickets per show – and you never pay for tickets or any additional (and crazy!) charges!

Stand up comedy, stand up comedians

A Few Stand Out Stand Ups in Boston in May & June

Big Names at The Wilbur

The Wilbur is a beautiful and historic theater located in the heart of downtown Boston. It was first opened in 1914 and has since been a major destination for both locals and tourists alike. The theater can hold up to 1,200 people, depending on the configuration, and has been host to countless events and performances over the years.

We’ve included a few of the hot tickets at The Wilbur in our highlights reel, including Kevin James, Samantha Bee, Tracy Morgan, and Leslie Jones. You can head over to The Wilbur’s website for ticket links.

Family-Friendly, But Oh, So Funny!

We started with a Brian Regan quote because he’s one of our favorites here at OTL. And that’s because he makes everyday life a lot funnier – think mayonnaise, dogs barking, and dinner parties!

Another reason is that his show is teen-friendly. It might not be the best for little ones, but 16+ – go for it!

Laugh Boston, Laugh!

You might have noticed a few shows at Laugh Boston on our highlights reel, but that’s just scratching the surface. Something’s happening in the club almost every day of the week – from stand-up to improv, national and local talent.

Two tickets, pizza, wings, and a Seaport Escape Bowl for two? There’s your next date night!

otl seat fillers, how to be a seat filler, seat filling
OTL Seat Fillers, seat filling, how to be a seat filler

Looking for a Particular Comedy Club in Boston?

We’re covering laughs from all angles, including a dedicated Boston comedy clubs page. So, be sure to bookmark OTL City Guides.

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