The Funniest Place on Earth: Massachusetts and the Modern Comedy Scene


By Colin Woodward

Massachusetts doesn’t get enough credit for comedy. For some reason, southerners think they have a distinct sense of humor. I can’t remember who said it (maybe Roy Blount), but as one southerner put it, “It’s hard to be funny when it’s cold out.”

Well, maybe not when you’re walking through a blizzard with a -20 windchill factor. But the Bay State ranges from bitter cold to oppressive heat. August days can get to 100 degrees. Bipolar weather can make for bipolar people. And comedy is often born of mental illness. Boston is known for its great sports teams, music, and stranglers. It has also produced some of the best comics ever.


The modern Massachusetts comedy scene goes back to before World War II. The deadpan duo of Bob and Ray, both from Massachusetts, got their start in the Boston area on the radio. Bob Elliott’s son, Chris (born in New York), would make a name for himself on the early David Letterman show and the bizarre and hilarious sitcom Get a Life and in movies such as There’s Something about Mary. David Letterman once said Bob and Ray were the “funniest people in this country, these guys are also two of the keenest observers of the American scene and the finest interviewers in the business.”

Many others who have made it in the late 20th century comedy scene were born in Massachusetts. Doug Stanhope and Denis Leary were born in Worcester. Leary even taught comedy at Emerson, which would become a Mecca for aspiring comedians. If you lived in central Mass, as I did, in the mid-90s, chances are you can quote from No Cure for Cancer verbatim. Now, though, I realize Leary stole his act from Bill Hicks. Score one for Dixie!

That said, Massachusetts has a history of original comedy. Penn Jillette, of the duo Penn & Teller, is not a stand-up comic, but he is one of the best and funniest magicians ever, who mixes heavy doses of comedy into his act. He’s also a bright guy who never stops talking and will go on NPR and use a word like “solipsism.” Penn’s from Greenfield, which is now mostly known for its rampant heroin problem.

Okay, Massachusetts isn’t always funny. I don’t find Dane Cook, John Krasinki, or B. J. Novak all that amusing, but Massachusetts can claim them, too.

Grow up in Mass and being funny is about as necessary to your survival as being a Red Sox or Celtics fan. Those winter nights are long, chief. So go to the packy and we’ll watch Nick DiPaolo (from Danvers) when you get back.

Ever heard of comedian Pete Holmes? You should. He’s funny guy in his mid-30s, has insightful things to say about google and our concept of knowledge, and he’s from Lexington. Oh, he also had his own show, which came on after Conan’s program for two seasons.

Bill Burr, regarded as one of the best comics working today, is from Canton. The Boston area can also claim Louie C.K., who was born in Washington, D.C., and lived for a few years in Mexico, but wound up in Boston by the age of seven. Louie C.K.’s dark, self-deprecating, occasionally surrealistic brand of comedy could not have emerged from anywhere. It’s not the stuff of the Blue Collar Tour. It is more fittingly a product of the dark New England mind. Oh, and he knows how annoying the Boston accent can be.

Lenny Clarke, known for his heavy Boston accent, was born in Cambridge. Steven Wright, one of the most unique comics ever, is also from Cambridge. Conan O’Brien is from Brookline. Amy Poehler: Newton. You can also add to that list Dana Gould, who is from Hopedale in Worcester County as well as Jack Gallagher, a stand-up who grew up just south of Boston and who played Larry David’s doctor on Curb Your Enthusiasm.

Steven Wright, Red Sox fan.

If you saw the 2002 documentary Comedian, it featured Jerry Seinfeld. It also tracked the try-too-hard career path of the not-so-likable whiner Orney Adams, who’s from Lexington, Mass. Adams was once represented by George Shapiro (played by Danny DeVito in Man on the Moon). Now, Adams has a wikipedia page with no photo.

Rob Corddry’s career is going better. Corddry, who was born in Weymouth, attended UMass-Amherst. For years, he was a fixture on the Daily Show as a correspondent. He’s appeared in movies such as Old School and on the late, great Curb Your Enthusiasm. He was a scene stealer in Hot Tub Time Machine, which spawned a sequel, also starring Corddry. Now, he stars in the Adult Swim show Childrens Hospital.

Rob Corddry.

Do you remember the Mac-PC ads? “PC” was played by John Hodgman, who specializes in heady comedy. He was born in Brookline in 1971 and was doing radio before he even graduated from high school. He played a prickish literary critic on Bored to Death and hosts a weekly podcast called Judge John Hodgman. He has also written three books.

Boston comics are not always over the age of 40. Bo Burnham, who specializes in musical comedy, became famous for internet videos he made before he finished high school. His Youtube videos have more than 100 million views, and he has almost two million followers on Twitter. Not bad for a guy from Hamilton who is in his mid-20s.


Paula Poundstone might have been born in Alabama, but her family moved to Sudbury when she was a few months old. Other ladies to emerge from the Boston comedy scene include Rachel Dratch, who is from Lexington and was on Saturday Night Live for years, and whose repertoire included a recurring idiotic Red Sox fan sketch. Mindy Kaling is from Cambridge and went to Dartmouth before she started doing stand-up. She played Boston native Ben Affleck in a play she wrote with a female friend, who played Matt Damon, before going on to The Office (her boss on the show, Steve Carell is from the Boston suburbs) and then her own show. Sarah Silverman, a native of New Hampshire, got her start in Boston at 17.

Fun fact: Jen Kirkman and I share a birthday, though she was born one year ahead of me in Needham. She does stand-up, wrote for Chelsea Lately, and is a best-selling writer. She was married for a not very long time and has no kids, which inspired her 2015 special I’m Gonna Die Alone (and I Feel Fine). Spoken like a true Massachusetter.


Jenny Slate is a comedian from Milton. She is the voice of Marcel the Shell, which became an internet sensation a few years ago. Jenny, unfortunately, dropped the f-bomb in her first SNL sketch back in 2009. She lasted only one season at SNL. But last year, she starred in Obvious Child, which was well-received. Slate also appeared occasionally on Parks and Recreation as the weirdly sexy and unhinged sister of rich moron Jean-Ralphio Saperstein.

Jenny Slate. AKA, “Marcel the Shell.”

Did you watch The Fighter? Basically, the movie was Rocky set in the Boston area. It featured Sue Costello, a comedian from the tough working class Dorchester. True to her roots, she hasn’t dropped her heavy accent since becoming well known. A scrapper, Costello has gone from having a television show to losing everything and fighting her way back again. In 2015, she was the headliner at the Women in Comedy Festival in Boston.


Some of the funniest people working today were not from Massachusetts, but nevertheless got their start there. Marc Maron, who is a walking encyclopedia of comedy, went to Boston University and stayed in Massachusetts for the early part of his comedy career before moving on to New York and then L.A.. In his latest book Attempting Normal, Maron relates a sad encounter with a Boston hooker, who turned off Maron with her “undeniable and annoying New England accent.”

Maron has had people like Barry Crimmins on his show. Crimmins is known for his social commentary and helped blow the Boston comedy scene wide open back in the 1980s. Also to emerge from the Boston scene were locals Steve Sweeney (from Charlestown) and Jimmy Tingle (from Cambridge). The funniest show on NPR is supposed to be Wait Wait Don’t Tell Me. But actually, it’s Car Talk, starring two goofball, wise-cracking mechanics from Cambridge. Boston is to comedy what New Orleans is to music.

President Barack Obama participates in a podcast with Marc Maron in Los Angeles, Calif., June 19, 2015.(Official White House Photo by Pete Souza)

When he was on Air America Maron sparred–and still does, if you watch the IFC show Maron–with Sam Seder. Seder, who does about equal parts comedy and political commentary, grew up in Worcester. Seder likes to bully people. One of his victims growing up (actually the two are best friends) was Jon Benjamin. Benjamin has had success in comedy and TV, including his own show, Jon Benjamin Has a Van, which lasted for one season on Comedy Central.

Back in 2010, Maron interviewed Mike Birbiglia. Maron’s attitude toward Birbiglia, who is from Shrewsbury, has ranged from sweetness to jealousy-fueled contempt. Birbiglia is known for his long-form joke telling and his not-so-funny battles with sleepwalking. He has appeared on Orange is the New Black and the radio show This American Life.

Listen to Maron’s podcast WTF and you’ll also hear a lot about the late Patrice Oneal, who was born in NYC but grew up in Roxbury. Oneal went to jail for 60 days when he was a teenager and said that’s when he learned that being funny helped him survive being locked up. Maron called Oneal a “tremendous force of comedy,” who had “some fucking magnitude.”


Patrice was a big comedian, who left us too early. Another such comic was John Pinette, who died in 2014 at the age of 50 from a heart attack. Pinette was born in Boston in 1964. Being someone of Irish descent from eastern Mass, he of course attended Catholic high school, in Malden. Pinette couldn’t hide his girth on stage, and he embraced it by doing memorable bits about food. One of his best known routines was about him virtually bankrupting Chinese buffets. Growing up in Massachusetts, my best friend in high school used to do this bit in the car with me. Pinette, though, might be best known for being the guy who got held up on the second-to-last episode of Seinfeld.

As did Marc Maron, Howard Stern went to BU, where he was influenced by the legendary disc jockey Charles Loquidara’s Big Mattress radio show. Emerson College in Boston, dedicated solely to communications and the arts, can boast many alumni who have gone on to big comedy careers, including Denis Leary, David Cross, Iliza Schlesinger (who won Last Comic Standing), and Jay Leno.

Another graduate from Emerson was the late Spalding Gray. Gray was born in Rhode Island, but majored in poetry at Emerson. Gray was an actor and writer, who performed legendary monologues that were dark and very funny. Gray was a contemporary of Eric Bogosian, who also made a name for himself doing monologues. Bogosian was born in Woburn. Like Spalding Gray, Bogosian has never done comedy, per se, but his raw honesty has gotten bigger laughs than many stand-ups ever have.

One of the funniest things I’ve heard in a while is Gilbert Gottfried and Mario Cantone doing a scene from When Harry Met Sally as Carol Channing and Herve Villechaize. Cantone, an Emerson alumnus, provided the voice of Carol Channing. Cantone, who is from Stoneham, a suburb of Boston, is known for his work on Chapelle Show, Sex and the City, and Broadway musicals.

The heyday of the Boston comedy scene is over, but Massachusetts still knows how to bring the funny. But is it right to think of there being a distinct Massachusetts sense of humor? Clearly, Massachusetts’s sense of humor is more sophisticated than what passes for funny in the rest of the country. It tends toward the bizarre, the black, the witty, the dry, and the sarcastic. Let’s face it, it can be mean.

It’s doubtful that someone from Alabama will find someone from Massachusetts funny on a regular basis and vice versa. People from Massachusetts have more comedy kin in NYC, L.A., and London than the Deep South.


Why is there such a rich history of Massachusetts stand-up? True American humor goes back to the eighteenth century. The funniest of the Founding Fathers was Ben Franklin who was born in–yep, you guessed it–Boston. Edgar Allan Poe was also born in Boston and let’s face, “Murders in the Rug Morgue” is huh-larious.

Circa 1692, The trial of George Jacobs for witchcraft at the Essex Institute in Salem, Massachusetts. (Photo by MPI/Getty Images)

Stand-up is a distinctly post-World War II phenomenon. It thrived in urban areas like New York, Boston, Chicago, and later L.A.. America has many urban areas, though, so why did Massachusetts become a hotbed of comedy when Milwaukee and Miami did not? Why would Mass, which some people see as puritanical and humorless when it’s not a bastion of godless liberalism, produce a Conan O’Brien and Steven Wright? How can a place that executed people for witchcraft create great comedy three hundred years later?

Well, 300 years is a long time. And though the Puritans were humorless, they were intellectuals. They founded Harvard and a true literary and philosophical tradition–steeped in the Bible though their outlook may have been. Massachusetts is the gold standard for American education. It’s the place where the elites from other states send their kids to college. Some are smart. Others are George W. Bush.

Massachusetts has a tradition as a smart place, a bookish place. Comedians aren’t just funny, they are very, very smart. Conan went to Harvard. So did John Updike, who worked at Harvard Lampoon while he was there. You also need a sense of humor if you’re going to be a lifelong Red Sox fan, who endures six months of winter every year.


Anyone can tell a joke. Not everyone can tell a joke well. And fewer still can put together a set of original material that makes people laugh for thirty minutes or an hour. The best comedians come from the northeast, because it has the country’s strongest intellectual tradition. Northampton, Massachusetts, probably has more used bookstores than all of Arkansas. Massachusetts has far too many colleges and universities to name–despite Spinal Tap’s manager’s claim (ironically of course) that Boston is “not a big college town.” As a comic, you could make a living just playing colleges in Massachusetts.

Stand-up comics are intellectuals at heart as well as true individualists. If you’ve heard of a certain comedy troupe, chances are it is not from Boston. Many people outside of New England think Massachusetts is a hotbed of socialism. It’s not. People there are more fiercely independent than other parts of the country. Massachusetters may like big government, but they also like their alone time. They will occasionally seek others out to drink, procreate, and watch Red Sox games, but mostly they want to do everything themselves. They are a stubborn lot.

One of the most unique and frightening things about doing stand-up is that you must do it alone. Should there be more than one person on stage with you, you are doing something else. Comics are brave, vulnerable, angry, and crazy. And for whatever reason, Massachusetts has made a lot of them.

Colin Woodward is an archivist and historian. He is the author of Marching Masters: Slavery, Race, and the Confederate Army, which is not especially funny.  He is writing a second book on Johnny Cash, who often was very funny.

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