The Five Best Fictional Bostonians of All Time

From Diane Chambers to Tobias Fünke.

We’re asking prominent locals who they think are the Best Bostonians of all time. Ryan Walsh, the singer/songwriter of Hallelujah The Hills and Boston magazine contributor, gives us his top picks—from the fictional realm. Play along by voting in our online game.

Tobias Funke

Arrested Development‘s Tobias Funke / Still from YouTube

Joelle van Dyne a/k/a Madame Psychosis a/k/a The PGOAT
Infinite Jest

Meet Joelle van Dyne: Experimental film actress, free form radio host, ex-BU cheerleader, possibly facially disfigured, possibly the prettiest woman of all time, constantly wearing a veil, and the star of the titular film that drives the novel’s plot. Those who watch ‘Infinite Jest’ and Joelle’s performance in it find it so entertaining they become entranced, literally watching it on repeat until they die (Wallace would’ve been horrified by the term “binge-watch”). Boston-residing or not, Joelle is one of the most complex, fascinating literary characters of the last century. In the novel, JVD hosts a local radio program, and you can hear people approximating what it might actually sound like here and here.

Terence Mann
Field of Dreams

In 1982’s Shoeless Joe, the novel which Field of Dreams is based upon, it’s not Terence Mann that Ray Kinsella enlists to help with a series of small rituals which ill summon the ghosts of dead baseball players in a cornfield in Iowa, but rather the king daddy of reclusive authors, J.D. Salinger himself. In fact, the book was originally entitled “The Kidnapping of J.D. Salinger” until laywers wisely advised against that, and it was no surprise that J.D. flipped out about his portrayal in the book regardless of the title. Thus we get James Earl Jones playing a fictional invention named Terence Mann. Mann is a classic Boston crank, telling Kinsella he’s no longer a public figure and shouting mockery of ’60s hippie ideals in his introductory scene. Kinsella then quotes from one of Mann’s books in a Hail Mary attempt to try to win him over, shakily reciting, “There comes a time when all the cosmic tumblers have clicked into place and the universe opens itself up for a few seconds to show you what’s possible.” Bonus points for creating a line from a non-existent book that sounds like it could actually originate from a classic piece of fiction. Mann’s transformation from heartless recluse to wide-eyed believer is to be commended for coming off as convincingly genuine, and the placement of Mann in Boston works so well because it’s entirely believable that the city would house such a textbook hardened cynic.

Diane Chambers

Shelley Long’s portrayal of a BU grad wannabe intellectual/bar waitress still resonates 28 years after departure from the show because it’s so simultaneously charming and insufferable. Like a lot of people you actually meet around here, her world exists inside of books, until she’s forced to confront the real world via the necessity of a day job. It’s watching Diane’s comically awkward struggle to communicate with a team of barflys that struck a chord for so many people who loved watching her slug it out inside a Boston pub, whether they lived in Southie or Alaska. But viewers from Boston very likely were reminded of a few people they knew when they tuned in every week.

Tobias Fünke
Arrested Development

We learn it right there in the pilot episode: “My name is Dr. Tobias Fünke. I was chief resident of psychiatry at Mass General for two years, and I did my fellowship in psycholinguistics at M.I.T. And this is “I’m a Bad, Bad Man” from Annie Get Your Gun.” All throughout Arrested Development, David Cross perfectly nails the vibe of a professional helper who can’t even recognize basic truths about himself. I declare with no exaggeration, this is one of the funniest television characters of all time, and Boston should be proud to claim this “analrapist” as our own. Bonus: Cross began his comedy career in Boston, bravely doing weird performance-art pieces at biker bars in Dedham and other area shitholes.

Sean Maguire
Good Will Hunting

The opposite of Tobias Fünke. Sean Maguire (played by Robin Williams) represents the kind of professional help you’d hope to encounter, and not unlike a lot of the great people you do actually meet in Boston when you’re a secret math genius with PTSD from Southie doing janitorial work at MIT.


Whom would you choose? Help us pick the Best Bostonians of all time.