Comedians Share Embarrassing Celebrity Encounters With Sting, Questlove, Scorsese and More at the Boston Comedy Festival

The Boston Comedy Festival is underway, and because you can’t always be there when you want to be in the comedyverse, we’re bringing you as much coverage as we can. This week we’ll keep you updated on what you’re missing in Boston with plenty of performances from Boston locals, Boston alums and just great comics like Barry Crimmins, , Judah Friedlander, Kendra Cunningham, Ms. Pat, Matt Braunger, Michelle Buteau, Chad Daniels, Tony Hinchcliffe and so many more.  Keep checking back daily for more updates like this one from Starstruck with Bethany Van Delft and Nick Chambers.

“We meet these people we admire, and we make it weird.”
-Nick Chambers, Starstruck

There is a very special shame that comes from messing up a celebrity encounter. The excitement of what you’re seeing and doing can give way to embarrassment all too quickly. And in some ways, it can be comforting to know that comedians still feel that way sometimes, given their relatively frequent brushes with famous folks. But in their festival show Starstruck: Close Encounters of the Awkward Kind, Boston comics and storytellers Nick Chambers and Bethany Van Delft afford their guests a sense of redemption.

The pair acknowledges they’re perpetually awkward, no matter how many chances they’re given to redeem themselves. “We’ve done it like a thousand times, and we never learn!”, joked van Delft. After sharing their own stories of celebrity-fueled shame (Nick’s was an impromptu serenade to Sting at Obama’s first inauguration, Bethany’s was accidentally negging Questlove after a DJ set), the pair ceded the stage to a trio of comedians and storytellers each armed with their own cringeworthy celebrity encounters.

TV Guidance Counselor host Ken Reid shared a pair of stories: first, about paying a busking Dave Matthews to not sing for three minutes in a park in England, and then about a spontaneous show of emotion during a conversation with Rhoda and Valerie star Valerie Harper. Comic Nonye Brown-West went next, recounting her failed attempt to befriend the cast of Entourage at a Goldman-Sachs holiday party. And Moth StorySLAM winner Christine Gentry recalled her charge from a Harlem mobster to deliver an envelope to Martin Scorsese during a charity event- which, she later learned, contained a detailed documentary pitch about, as she put it, “dogs in cinema.”

The next stage of the show, in my estimation, is what makes enduring these awkward moments as a group worth it. With every metaphorical kicking of ourselves as we mercifully end these uncomfortable moments, we wish we could have a chance to do it over again. Recognizing that need, Chambers and Van Delft built a “mulligan mechanism” into the show. After hearing the three stories, audience members voted on which one they’d most like to see redeemed; then, a troupe of actors dubbed the “Redo Crew” re-enacted the chosen story, but with a twist: the ending goes well! The Boston Comedy Festival crowd selected Gentry’s story most redeemable, and the Redo Crew’s version had Gentry taking credit for the treatment and teaming up with Scorsese to make the meticulously planned film.

Starstruck will live on as a podcast with periodic live recordings and more opportunities for comics and storytellers to relive their missteps with the famous. So get your stories ready, one day it may be your turn to tell it for a shot at redemption!

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Amma Marfo

Amma Marfo is a writer, speaker, and podcaster based in Boston, MA. Her writing has appeared in Femsplain, The Good Men Project, Pacific Standard, and Talking Points Memo. Chances are good that as you're reading this, she's somewhere laughing.