Power Rank

The 10 best fictional Bostonians of all time, ranked

Boston has served as home to many a memorable character. Cops. Crooks. Crooked cops. And of course the occasional orphaned genius MIT janitor with trust issues. Because we can't spend all our time eating lobster rolls, we searched our souls/movie collections/IMDB and came up with these top-10 fictional Bostonians of all time.

Frank Galvin Best Fictional Characters BOS
Twentieth Century Fox Film Corporation

10. Frank Galvin
The Verdict
Forget The Practice, Boston Legal, A Civil Action, and The Paper Chase, because The Verdict is THE Boston courtroom drama for the ages (you can also forget Ally McBeal, Legally Blonde, Boston Common, With Honors, Mystic River, 21, Fever Pitch (ugh, why?!), The Next Karate Kid, Crossing Jordan, Rizzoli & Isles, Company Men, R.I.P.D., and ESPECIALLY The Town for numerous violations such as really bad accents). Frank Galvin, an alcoholic, down-on-his-luck ambulance chaser, gives redemption a shot by refusing an ample settlement in lieu of trying the case of a comatose woman. Major cojones. Spoiler alert: by doing the right thing, he wins one for justice. Case closed.

Thomas Crown Best Fictional Characters BOS
Mirisch-Simkoe-Solar

9. Thomas Crown
The Thomas Crown Affair (1968)
Steve McQueen’s Thomas Crown is the archetypal ultra-suave, polo-playing millionaire "cool guy with a dark side". And he’s ours. He dines at Anthony’s Pier 4 like a real Boston gentleman would... in the late 1960s. Fueled by boredom, Thomas orchestrates elaborate heists carried out by others and then deposits the dough (that he doesn’t need) into a Swiss bank account. Like Robin Hood, but without the generosity. Regardless, he’s so debonair that he can silently chess-flirt with his foe/love interest Vicki (old-school hottie Faye Dunaway) just by glancing at his king. Check and mate (get it? She did).

Lt. Jimmy Dove Best Fictional Characters BOS
MGM

8. Lt. Jimmy Dove
Blown Away (1994) (No… not Blown Away 1993 with the Coreys)
Looking for atonement/karmic reversal, Northern Ireland terrorist Liam McGivney gives up bombs, relocates to Boston, changes his name to Jimmy Dove (really?), and becomes a hero-level cop... who disposes of bombs (he should have started with his own name). Of course, he blends in like a proper local Irish ex-pat by drinking at the neighborhood pub with his Uncle Max. When he’s not being stereotypical, he plays cat-and-mouse with his insane and explosive (pun intended) nemesis Ryan Gaerity in an effort to protect our fair city. In the end, he saves a lot of people, the Hatch Shell, The Pops, The Esplanade, and the 4th of July. So there’s that.

7. Ted (and John)
Ted
He’s a foul-mouthed, sex-crazed, cigar-chomping, weed-smoking, booze-drinking sentient teddy bear. With a heart of gold. And stuffing. Ted and his best friend/Thunder Buddy, John, are city pros: they live in the South End, go to Charlie’s Sandwich Shoppe, visit the aquarium, stroll through the Common and Public Garden, catch a show at the Hatch Shell, eat at Gaslight and Sorellina (“Ciao Baby’s”), and confront their creepy adversary Donny at Fenway. They also party BIG TIME at Ted’s place in Chelsea with their childhood idol Sam Jones, aka Flash Gordon. Question: why doesn’t Ted ever wear a Bruins jersey? That seems obvious/awesome.

6. Francis "Frank" Costello
The Departed
Mr. "I want the environment to be a product of me," Costello (inspired by real-life goodfella Whitey Bulger) is about as subtle as a hammer and twice as dangerous. He is everything you want in a mob boss. He quotes James Joyce, cracks wise, cracks skulls, mentors his charges, eats flies, kills more people, and dispenses street-smart wisdom nuggets. Like, "The only one that can do what I do is me.” And, "You can learn a lot, watching things eat." Or maybe, "Enjoy your clams, (censored)." Pretty badass.

5. Will Hunting
Good Will Hunting
Will Hunting exemplifies the duality of Boston: wicked tough and wicked smaht. Total metaphor. He puts an economic theory smackdown on a Hahvahd kid while draining beers with his buddies (pour one out for the Bow & Arrow). He works with a sledgehammer and works over complex equations. And he’s Southie through and through. From Dunkies to the L Street Tavern to The Tasty (also pour one out for The Tasty), Will’s story is a love letter to Boston. And townies. And apples.   

Sgt. Donny Donowitz Best Fictional Characters BOS
Universal Pictures

4. Sgt. Donny Donowitz
Inglourious Basterds 
With shouts of "Teddy f*ing Ballgame" and some ominous taps of the baseball bat, the "Bear Jew" menaces Third Reich lackeys, then brains them with his Louisville Slugger. You only need to know two things about Donny: loves Boston, hates Nazis. Like the rest of the Basterds, Sgt. Donowitz is deeply dedicated to the cause of dee-stroying the bad guys. As in he sleeps holding a knuckle knife. His swan song involves infiltrating the cinema and gleefully filling Adolf full of bullets. Not a bad way to go out.

3. Connor and Murphy MacManus
The Boondock Saints, The Boondock Saints II: All Saints Day
Like Chicago’s Blues Brothers, The Boondock Saints are on a mission from God... to rid Boston of "evil men". Noble. But instead of using music, they use guns. And toilets. Like the one Connor drops on some Russian mobsters to save Murphy. They are revered as vigilante folk heroes and get help from just about everybody, including FBI Agent Smecker who tracks their... umm... "ridding" spree. When they get shot, they cauterize their wounds with a regular household iron. Too bad that happened before individually mandated Massachusetts health insurance.

Spenser Best Fictional Characters BOS
ABC

2. Spenser
Spenser: For Hire
NYC has John McClane, we have Spenser (with an "s")... proving once again that we’re better. How can "yippee-ki-yay" compete with Spenser’s cars (’66 Mustang, ’87 Mustang 5.0 GT, ’66 Mustang GT), his boxing, his cooking, his Beretta 9mm, his poetry, his way with the ladies, his sax-addled theme song, his workouts, and his sleuthing? No contest. Fun fact: his firehouse home base in Beacon Hill was later home to The Real World: Boston cast (also fictional).

1. Hillary Norman "Norm" Peterson
Cheers
Boston = Cheers and Cheers = Boston. Whether we like it or not. And when you think of Cheers, your thoughts drift to that lovable everyman Norm. "Noooorrrmmmmm!" Everyone knows his name... just like that catchy theme song suggests they should. He is the perpetual customer perched on his barstool sipping brews, racking up a multi-volume bar tab, and bantering with everyone (mostly Cliff) within earshot. Norm is best known for his self-deprecating quips, and there are MANY gems. Like, "Women. Can’t live with ‘em, pass the beer nuts." And, "It's a dog-eat-dog world, Woody, and I’m wearing Milk-Bone underwear!" Who needs a beer?