TV

Since the very beginning of “Saturday Night Live,” Boston has played a key part in the New York institution.

By Kevin Slane

February 13, 2025 | 6:13 AM

9 minutes to read

The very first mention of Boston on “Saturday Night Live” came on October 18, 1975, in the show’s second episode.

In one of the show’s famed commercial parodies, social activist Jerry Rubin (of The Chicago Seven fame) plays himself, selling wallpaper that features slogans of anti-war protests and anti-establishment movements of the era.

As Rubin takes viewers on “a protest march down Memory Lane,” the camera pans past dozens of hand-painted messages, including “Free the Boston Five,” a nod to a real trial and protest involving five men who led a local effort in the 1960s to return their draft cards to the Attorney General in protest of the Vietnam War.

Wallpaper is a fitting metaphor for Boston’s place in the 50-year history of “Saturday Night Live,” which will be commemorated in a three-hour special this Sunday. It’s been there in the background the whole time, and even when you didn’t notice it, it helped tie the room together. 

But when certain cast members with a penchant for dropping their Rs brought their own comic stylings to Studio 8H, Boston’s presence — like a garish floral wall pattern — snapped into focus.

Ahead of “SNL50,” we’re looking back at Boston’s role in the show, from playing the New York institution’s antagonist in the sports world to exporting some of our funniest thespians to Rockefeller Center.

Note: Many early “SNL” sketches are only viewable within full episodes streaming on Peacock. Where possible, we linked to specific episodes that contain the mentioned clip.

Click the links below to jump directly to the following information:

Boston Sports on “SNL”

One of the first “Weekend Update” jokes to mention Boston came near the end of the first season in episode 22, when Chevy Chase used the iconic photo of Bobby Orr’s 1970 overtime Stanley Cup-winning goal as a punchline amidst Orr’s contentious contract negotiations with the Bruins.

“Boston Bruin Bobby Orr, the superstar defenseman, announced that he will give up hockey to enter in the freestyle diving event in the ’76 Olympics,” Chase said. “He is shown here executing a perfect swan dive into solid ice.”

As the years went by, the prevalence of specific Boston sports teams being mentioned on “SNL” ebbed and flowed based on the team’s success. 

Celtics great Bill Russell hosted the show in its fifth season, playing both a terrible high school basketball coach and an irate version of himself on a sports radio show where none of the callers have heard of basketball.

Jokes about the Red Sox cropped up after the team lost the 1986 World Series to the Mets, and the recurring “Boston Teens” sketch featured plenty of Sox references, including one guest appearance from Nomar Garciaparra himself on October 18, 2000. 

There was even a sketch dedicated to Don Zimmer (played by Horatio Sanz), in which various guests on his talk show tossed him to the ground in the style of Sox ace Pedro Martinez.

And Kenan Thompson parodied slugger David Ortiz in numerous “Weekend Update” desk segments, zeroing in on Ortiz’s propensity to serve as a spokesman for any company who asks.

“SNL” occasionally made time for Boston sports figures outside of the Big 4 teams as well. Rich Hall played Doug Flutie in a Season 10 sketch in which South African bishop Desmond Tutu (Eddie Murphy), fresh off his Nobel Prize win, accidentally breaks the BC quarterback’s Heisman Trophy.

Then in 1994, Stoneham native Nancy Kerrigan hosted the show, which featured an opening monologue in which every question came *this* close to asking about Tonya Harding without actually doing so.

All of those pale in comparison to the sheer volume of Patriots parodies that began showing up on “SNL” during the team’s unprecedented two-decade run of success. 

Before the start of the Brady/Belichick/Kraft dynasty, there were only two notable mentions of the team on “Saturday Night Live.” 

The first came before the 1986 Super Bowl, in which a Benedictine monk (Jon Lovitz) who foolishly wants to wager the abbey’s profits on the Patriots serves as the sketch’s punchline. 

The second, from 1990, came during the brief time Victor Kiam owned the team, with Phil Hartman lampooning the Remington Shaver pitchman after he publicly disparaged a Boston Herald reporter that sued the team alleging sexual harassment.

Then came the 2000s, in which every move the Patriots made seemed to show up on “SNL.” Quarterback Tom Brady served as host in 2005, playing along with jokes about him being handsome and one-upping Peyton Manning. 

But as the years passed and the Patriots trophy case filled up, the tenor of the humor shifted. Sketch topics of the 2010s included Brady supporting Donald Trump or having a deal with the Devil himself (Jason Sudeikis). Deflategate, which for a brief moment in 2015 was a national obsession, received commensurate coverage on “SNL.”

Over the years, everyone from cast members Taran Killam and Beck Bennett to hosts Channing Tatum and Newton native Jon Krasinski have played the former Patriots signal-caller.

The whole Patriots extended family was represented as well, whether it was Bill Belichick (Bobby Moynihan, Beck Bennett), Brady’s ex-wife Gisele Bundchen (Kristen Stewart), or Rob Gronkowski (West Newbury native John Cena).

The Patriots dynasty may be over, but Brady, Belichick, and Gronkowski still loom large in the public consciousness. Don’t bet against at least one of them getting the “SNL” treatment again sooner rather than later.

Boston Politicians on “SNL”

The history of Massachusetts politicians being relevant on a national stage predates “SNL,” but the show made sure to lampoon every one of them along the way, especially those who sought the highest office in the land. 

The longest-suffering punching bag was the late Ted Kennedy, who was the subject of a recurring impression by Bill Murray and later portrayed by Phil Hartman.

Perhaps most famously, in the cold open of the 1979 Bill Russell-hosted episode, Kennedy (Murray) is late to his own presidential campaign rally, arriving soaking wet in a nod to the infamous Chappaquiddick incident.

The entire Kennedy family took it on the chin from “SNL” for decades. During the 1991 trial for William Kennedy Smith, an “SNL” sketch interviewed prospective jurors, who spent five minutes under oath sharing their honest opinions about the whole family. Even the Kennedy least likely to be welcome at the family’s Hyannisport compound, Robert F. Kennedy Jr., has popped up on “SNL” – or at least RFK Jr.’s brain worm has, anyway.

Other Massachusetts officials faced the music on “SNL” as well. Tip O’Neill was the subject of multiple jokes about his weight during his tenure as Speaker of the House. During his 1988 presidential run, Michael Dukakis was portrayed by Jon Lovitz as cold, uninviting, resigned to defeat, and in one sketch, as an alien in disguise.

Paul Tsongas, who ran in the 1992 Democratic primary, was played multiple times by future Senator Al Franken, and got dinged (along with Dukakis) by Kevin Nealon on “Weekend Update”.

“In the New Hampshire primary, Paul Tsongas beat the other democrats on Tuesday night with 34% of the vote,” Nealon said “Although that was an important victory, Tsongas is already being compared to Michael Dukakis and will have to campaign vigorously to prove he’s not another geek — uh, Greek from Massachusetts.”

John Kerry, played by longtime New Hampshire resident Seth Meyers, was played as an overly verbose stuffed shirt, especially when facing off against plainspoken George W. Bush (Will Forte).

The most recent presidential hopeful from Massachusetts, Elizabeth Warren (played by Kate McKinnon), was certainly treated better by the show than any Kennedy was, and the real-life Warren even showed up on a 2020 episode alongside McKinnon. But a Town Hall sketch — which portrayed her as hyper-competent but broadly disliked by the average voter — was brutal in its own way.

The ‘SNL’ Stereotypical Bostonian

The very first “SNL” cast also had its very first Bostonian — or Cantabrigian/Welleslian, if we’re being precise — in Jane Curtin. There were plenty of sketches that made mention of Curtin being from Boston, most notably a Season 4 cold open in which John Belushi predicted that when “SNL” ended, she would be forced to move home and perform improv to small rooms.

But the idea of playing a stereotypical Bostonian (whose last name wasn’t Kennedy) didn’t really take root until the 1990s. That’s when longtime New Hampshire resident Adam Sandler debuted recurring character Tony Vallencourt.

Vallencourt’s first appearance came in the December 1992 sketch “What’s the Best Way?,” which featured Sandler, host Glenn Close, and Phil Hartman as game show contestants whose only questions involved how to drive from one New England landmark to another.

Years before “The Californians” made Los Angeles traffic a punchline, the trio (who all love candlepin bowling) took turns discussing the merits of various routes from Quincy to the Jordan Marsh in Bedford, New Hampshire.  

Vallencourt returned in 1993 — this time in a sketch that was apparently so poorly received that it didn’t make it into the recut episode streaming on Peacock — and for a final time in 1995 as a Celtics superfan mourning the closing of the Boston Garden.

Four years later, Lexington native Rachel Dratch debuted her take on the stereotypical Bostonian with The Boston Teens. Dratch originated the “Denise” character at Second City in Chicago, with Tina Fey playing her mother. Once it reached “SNL,” Fey bowed out and Jimmy Fallon stepped in as Denise’s boyfriend, Pat “Sully” Sullivan.

Dratch filled the sketches with hyper-specific references to Lexington, including using the name of a science teacher from her middle school and a patch of woods in the town where high schoolers occasionally got busted for drinking. The list of regional shoutouts embedded in the sketches is too long to list, but includes gems like Cumberland Farms, Anthony’s Pier 4, Wachusett Mountain, and Foxwoods. 

Burlington native Amy Poehler, who worked with Dratch at the now-closed Lexington restaurant Chadwick’s, often joined in on the fun, as did longtime New Hampshire resident Seth Meyers. The Boston Teens made sure to recur when locals hosted as well; Brookline native and former “SNL” writer Conan O’Brien made an appearance, as did Cambridge native Matt Damon. Damon’s childhood buddy, Ben Affleck, managed to make three appearances as Sully and Denise’s pal Donny Bartalotti.

In total, the Boston Teens appeared a dozen times during Dratch’s run on the show, later returning for a 13th and 14th time during Fallon-hosted episodes in 2011 and 2017.

While the current “SNL” cast doesn’t have anyone from Boston, a few have played around with the tropes, most notably Heidi Gardner as Every Boxer’s Girlfriend from Every Movie About Boxing Ever, who lives at 343 Donnie Wahlberg Way.

The writers’ room has also featured both Boston natives like Sam Jay and New England natives who have an eye for Boston-specific humor, like current co-head writer Streeter Seidell.

Seidell was the brains behind both the Revolutionary War sketch from 2018, in which colonists from Boston (including Dratch) and Philadelphia (including Fey) traded barbs ahead of the Patriots-Eagles Super Bowl.

“Revolutionary War” is part of an “SNL” tradition that began with 1984’s “Salem Court” and continued with 1993’s “Salem B**** Trial” sketch of blending contemporary Boston mannerisms and insults with a centuries-old setting. 

“I was watching [HBO series] ‘John Adams,’ and a lot of the early episodes are of New England people being extremely aggressive and loud and kind of obnoxious,” Seidell told Boston.com of his inspiration for the sketch.

Seidell also co-wrote the 2016 “Dunkin’ Donuts” sketch starring Casey Affleck, which spawned a pair of sequels featuring Canton native Bill Burr.

Affleck told Boston.com that he was surprised that the sketch connected, assuming that “no one outside of the three blocks where we’re shooting” would understand the point of reference.

Thankfully, the “SNL” viewing audience has had 50 years to get in on the joke.

Source