The Queue

Ahead of Matt Damon hosting the May 9 episode of "Saturday Night Live," take a look back at the Cambridge native's three decades of appearances on the show.

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Matt Damon will be hosting the penultimate episode of “SNL” Season 51 this weekend, with fellow New Englander Noah Kahan joining him as musical guest.

Damon will be hosting “SNL” for the third time — though it may feel like more than that, thanks to his four additional cameo appearances over the years. Damon even joked about his ubiquity on the show during his most recent appearance in 2024, when he was given two “Five-timers” jackets before “SNL” vet Kristen Wiig was given her own.

In total, the Cambridge native’s legacy on the show spans nearly 30 years. He was first impersonated on the show by Jim Breuer in 1998, made his first cameo appearance in 2001, and landed his first host gig in 2002, helming the Season 28 premiere with Bruce Springsteen as musical guest.

In honor of Damon’s return to Studio 8H, I’m taking a look back at Damon’s most memorable “SNL” appearances. (Spoiler alert: One of them is impossible to watch.)

Matt Damon’s best “SNL” moments

Boston Teens: Springsteen Concert (2002) 

Damon’s only “Boston Teens” appearance is basically impossible to watch online (or anywhere) 24 years later. That’s because the sketch, which takes place at a Bruce Springsteen concert, features The Boss performing “Dancer in the Dark,” and “SNL” didn’t think about clearing the music for digital use back in 2002 when YouTube didn’t exist yet.

The Peacock upload of Damon’s episode is also missing his opening monologue due to music used for a dance-off between Justin Timberlake (Damon) and Britney Spears (Amy Poehler), but you can still find the video on unofficial channels if you search hard enough. The best you can do for Damon’s “Boston Teens” sketch is read a typo-filled transcript, which features shoutouts to Kappy’s Liquors, the Fleet Center (“You’ll never be the Garden!!”), and “Good Will Hunting.”

Damon and Seth Meyers as Red Sox fans (2002)

The Red Sox were still cursed by the Bambino back in 2002, so when the Yankees were eliminated by the Angels in the ALCS, Damon and Meyers (who grew up in New Hampshire) visited the “Weekend Update” desk to offer condolences. (“When the ball went through Buckner’s legs in ‘86, I was hospitalized for like a week.”)

SNL Digital Short: Best Friends (2011)

Andy Samberg and co. haven’t yet covered this 2011 Digital Short on their podcast, but I’m guessing it won’t make the Lonely Island criterion collection. Nevertheless, the 57 seconds featuring Damon as a handsome homeless man (and best friend to Samberg, Katy Perry, and “brilliant lunatic” Val Kilmer) is the best part of the short.

Kavanaugh Hearing Cold Open (2018)

Damon’s “SNL” peak was this 2018 cold open, in which he channeled the simmering frat boy energy of Supreme Court Justice Brett Kavanaugh prior to his confirmation – a role Damon reprised when he hosted later that year. Keep an eye out for Lexington native Rachel Dratch, making a cameo herself as Sen. Amy Klobuchar.

Tommy Ray Donovan (2018)

My personal favorite from Damon’s 2018 holiday episode is the Westminster Daddy Show, a dog show for hot dads. But this is Boston.com, so I have to highlight Damon’s appearance as Tommy Ray Donovan, husband of Heidi Gardner’s recurring Boston-coded Update guest, “Every Boxer’s Girlfriend from Every Movie About Boxing Ever.” Born in the back of the Cheers bar, Tommy may not be a pedigreed Daddy. But he’s a loving father to Mikey, Nicky, Peppers, Keno, and the couple’s upcoming fifth child, who will be named Gronk regardless of gender.

Play or Skip

Have a show you can’t stop watching? Email me about it at [email protected], and your recommendation may appear in a future edition of The Queue.

Press play on these movies and shows:

“Marty Supreme” (2025): One of my favorite movies of 2025, “Marty Supreme” brings the same jittery energy of 2019’s “Uncut Gems” to 1950s New York City, where Marty Mauser (Timothee Chalamet) moves from one hustle to another in his quest to be the world’s greatest ping-pong champion. Marty’s many flaws are evident, and his motives are transparent, but you understand why anyone unlucky enough to enter his orbit (including a never-better Gwyneth Paltrow) keeps falling for him. (HBO Max)

“Gary” (aka “The Bear”): Hulu announced earlier this week that the fifth and final season of “The Bear” will debut on June 25. What Hulu didn’t announce was this secret episode, which showed up unexpectedly on the streaming service on Tuesday. Set before the events of the show, “Gary” sends Mikey (Jon Bernthal) and Richie (Ebon Moss-Bachrach) on a short road trip to Indiana, where hijinks and at least one emotionally devastating diatribe ensue. (Hulu)

“Send Help” (2026): When a downtrodden corporate employee (Rachel McAdams) and her horrible CEO (Dylan O’Brien) end up on a deserted island, Linda’s love for the show “Survivor” suddenly becomes very relevant. Also relevant: After being mocked and bullied by her boss back in the real world, Linda now holds the upper hand over the badly injured Bradley. With Sam Raimi (“The Evil Dead”) at the helm, you know an equal dose of laughs and gasps are in order. (Hulu)

But go ahead and skip this one:

“Citadel” (Season 2): The second season of this Prime Video spy thriller is competently made, but less than 48 hours after cruising through its seven episodes, I’m struggling to recall a single standout moment. That shouldn’t happen when your show features Stanley Tucci and Matt Berry. (Prime Video)

End Credits

That’s a wrap on this edition of The Queue. If you’re a fan, please consider recommending this newsletter to your friends.

Until next time, good stream hunting, everyone!

— Kevin