Big Jay Oakerson: The Greatest Yapper Alive Tour LIVE at The Wilbur

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About Big Jay Oakerson

Big Jay Oakerson is one of the most beloved and hilarious stand-up comedians working today. Known for his explosive energy, fearless crowd work, and no-holds-barred comedic style, Oakerson has built a massive following through his live shows, podcasts, and television appearances.

He is the co-host of the wildly popular podcast The SDR Show and has appeared on Comedy Central, Netflix, and numerous other platforms. His live performances are legendary for their spontaneity, audience interaction, and the kind of raw, unfiltered comedy that keeps fans coming back show after show. The Greatest Yapper Alive Tour is his latest and most ambitious touring project yet.

Event Details

Date: Saturday, January 23, 2027
Time: 7:00 PM (Doors open at 6:00 PM)
Venue: The Wilbur, 246 Tremont St, Boston, MA 02116
Age Requirement: All ages welcome
Ticket Limit: Overall 8 ticket limit per order

About the Venue

The Wilbur is one of Boston's most beloved comedy venues, located in the heart of the Theater District at 246 Tremont Street. With a capacity of approximately 1,000 guests, The Wilbur offers an intimate yet vibrant atmosphere with excellent sightlines, a full bar, and easy MBTA access from the Green and Orange Lines. It is widely regarded as Boston's premier destination for world-class stand-up comedy.

What to Expect

Big Jay Oakerson's live show is a masterclass in crowd work, raw comedy, and high-energy performance. Expect approximately 75–90 minutes of non-stop laughs, audience interaction, and the kind of fearless, unscripted comedy that has made Oakerson one of the most in-demand touring comedians in the country.

This is a solo headlining show — arrive early, grab a drink, and get ready for one of the best nights of comedy you'll experience in Boston this year.

Ticket Information

Price Range: $66+. Official tickets via Ticketmaster. Resale tickets via VividSeats. There is an overall 8-ticket limit per order. Secure your seats early — this show is expected to sell out!

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All sales are final. Show times subject to change. Valid photo ID may be required for entry.