The 25 most insufferable characters in film history
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The 25 most insufferable characters in film history

In this life, you'll meet all kinds of people. Some will be delightful, some will be infuriating and a precious few will check that box marked "insufferable." You know the type. They may be friends, they may be coworkers or they may be flesh-and-blood family. Given that art holds the mirror up to nature, you will definitely encounter these exhausting creatures in movies. Sometimes they'll sour your viewing experience; other times their insufferableness is the point of the portrayal. Which characters really drilled into our last nerve? Try these 25 on for size.

 
1 of 25

Daniel LaRusso

Daniel LaRusso
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Ralph Macchio’s Daniel-san comes on a little strong in the first “Karate Kid" but not to the extent that he deserves a series of ever-worsening whuppings from the Cobra Kai gang. He’s far less likable in the execrable sequel as a tagalong on Mr. Miyagi’s Okinawa homecoming. But Macchio, either out of boredom or contempt for the character that made him a star, dials up the gregariousness to a suffocating degree in the third film, wooing poor Robyn Lively with the ferocity of a coked-up Benjamin Braddock. It doesn’t help that Robert Mark Kamen has written Daniel as an utter sap, but Macchio’s portrayal is so colossally unsympathetic that you’re rooting for Thomas Ian Griffith’s ponytailed heavy every step of the way.

 
2 of 25

Leo Getz

Leo Getz
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Joe Pesci’s portrayal of irritating federal witness Leo Getz in 1989’s “Lethal Weapon 2” marked a comeback of sorts for the Jersey-born actor; at the time, it was fun to see the “Raging Bull” co-star work a comedic twist on his spark plug gangster persona. After his Oscar-winning turn in “Goodfellas," however, Pesci’s pint-sized antics began to curdle into shtick. His two unnecessary encores as Leo in the third and fourth “Lethal Weapon” sequels represent the nadir of his film career. The character’s sole function in both films is to work a new variation on his “they f*** you at the drive-thru” bit.

 
3 of 25

Anakin Skywalker

Anakin Skywalker
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Let’s give Jake Lloyd a break. George Lucas’ writing of little Anakin Skywalker in “The Phantom Menace” has all the depth and nuance of a second-tier “Our Gang” character. Lucas didn’t completely screw up the future Darth Vader until “Attack of the Clones," where teenage Ani (Hayden Christensen) is portrayed as a sullen, sand-loathing jackāss. The prequel trilogy is far more fascinating (and prescient) than many people realize, but the tragic arc of its main character is undermined by this pouty characterization of incipient fascism.

 
4 of 25

Scarlett O'Hara

Scarlett O'Hara
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Plantation princess Scarlett O’Hara is as iconic as she is detestable. Vivien Leigh’s performance is so brilliantly overheated that you can’t help but give yourself over to her story, but, dear God, does this spoiled daughter of the Confederacy challenge your sympathies every step of the way. Unfortunately, the characters around her — save for Mammy (Hattie McDaniel), Pork (Oscar Polk) and Prissy (Butterfly McQueen) — are just as rotten. And yet none of them abuse the name “Ashley” with such ear-splitting abandon.

 
5 of 25

Phineas

Phineas
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Larry Pierce’s slavish adaptation of John Knowles’ heavy-handed coming-of-age novel ("A Separate Peace," the bane of every high school English student’s existence) strands us at a New England boarding school where well-to-do white boys get into all kinds of banal mischief. The ringleader of this alleged fun is Phineas, aka Finny, who’s played with blunt-force vainglory by John Heyl. It’s not Heyl’s fault; he plays the doomed scamp as written. But as in the book, you’re repelled by Finny and his obnoxious Super Sūicide Society of the Summer Session antics. You very much want him to take that tumble off the tree limb — and you’d like the rest of his classmates to follow suit.

 
6 of 25

Sam Witwicky

Sam Witwicky
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It was Steven Spielberg’s brilliant idea that the story of the first “Transformers” movie should be about a boy and his first car. Sounds charming and sweet, no? Not in the hands of mayhem merchant Michael Bay, who negligently allowed Shia LaBeouf to “No, no, no, no, no!” his way through three narratively incoherent films. Sam’s constant state of distress is exhausting as are the movies (particularly “Revenge of the Fallen”). He’s not entirely extraneous; the writers always ginned up some contrivance to make his character integral to the plot. But therein lay the problem: Nobody wanted to see a Transformers movie about a boy and his car; they wanted to see giant robots smack each other silly. As for a girl and her car, that turned out to be pretty spiffy in “Bumblebee” — which also happened to be the first Transformers movie not directed by Bay.

 
7 of 25

Drop Dead Fred

Drop Dead Fred
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Though Ate de Jong’s black comedy is, to some extent, an admirably subversive studio film about the lasting effects of childhood emotional abuse, there’s no getting around Rik Mayall’s irritating portrayal of the titular imp. Whereas the late British comic was brilliantly abrasive as anarchist Rick on “The Young Ones," he’s completely unhinged as Phoebe Cates’ imaginary friend (who’s returned to “help” her cope with numerous adult crises). “Drop Dead Fred” was supposed to establish Mayall as a comedy superstar in the U.S., but it did the exact opposite.

 
8 of 25

Willie Scott

Willie Scott
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“Innn-deeeeeee!” The good of Kate Capshaw’s legendarily grating portrayal of Willie Scott in the most relentlessly entertaining “Temple of Doom” is that it evokes a glorious degree of exasperation from Harrison Ford; he’s absolutely beside himself that he has to field complaints from a pampered showgirl while he’s scrambling to save their skins. It’s a hoary bit of cliffhanger business, but it brings out the most entertaining version of Indy. So for this reason alone, Willie is…an effective character. That said, the harsh frequency of Capshaw’s whine could cut through the door of a vault.  

 
9 of 25

Rupert Pupkin

Rupert Pupkin
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“Jerry, let me show you a picture of my pride and joy.” Insufferable, pitiful and ultimately dangerous – that’s would-be comedian Rupert Pupkin in Martin Scorsese’s masterful cringe-fest, “The King of Comedy." Robert De Niro is superb as a deluded loner skittering around the fringes of a world where he’ll never find success; in many ways, his perpetual smile and cheery demeanor are more menacing than Travis Bickle’s vengeful screeds. But while it’s a great performance, it ain’t exactly a party to spend 109 minutes in Rupert’s company. It’s skin-crawling stuff.

 
10 of 25

Charlie Bodell

Charlie Bodell
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Nicolas Cage is an actor who makes strong choices.  Very strong choices. Strong as the comic book character who gave him his stage name. In Francis Ford Coppola’s nostalgic “Peggy Sue Got Married," Cage plays “Crazy” Charlie Bodell with a highly affected nasal drawl and a desperate-to-be-loved energy that evidently repelled the film’s star, Kathleen Turner (“The way I saw it was, yeah, he was that asshōle”). He’s such an overwhelming cad that you have trouble buying the couple’s heartwarming reconciliation at the film’s conclusion. You’re bummed Peggy Sue stuck with this jerk.

 
11 of 25

Sidney Falco

Sidney Falco
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Tony Curtis is magnificently skeezy as a small-time press agent who needs to get back in the good graces of king-making gossip columnist J.J. Hunsecker or find a new line of work. J.J. famously calls Sidney “a cookie full of arsenic," and Curtis embodies this characterization throughout. At first it appears he may have a shard of decency stuck somewhere deep inside of him, but it’s easily dislodged when Hunskecker dangles the possibility of Falco guest-writing his column while he’s on vacation.

 
12 of 25

Napoleon Dynamite

Napoleon Dynamite
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Jon Heder briefly, inexplicably became a star on the strength of his deeply annoying portrayal of slack-jawed dweeb Napoleon Dynamite. Some audiences believed this act to be some kind of absurdist work of art; a kissing cousin of Bill Murray and Gilda Radner’s nerd characters on “Saturday Night Live." It’s comedy. Your mileage may vary. But if “Napoleon Dynamite” is not for you, it is  very much not for you.

 
13 of 25

Janie Bailey

Janie Bailey
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The most convincing argument for George Bailey jumping off the Bedford Falls Bridge resides at home. While Frank Capra did just about everything right at just about every level with this Yuletide classic, he whiffed badly on the writing and casting of the children. These are without a doubt some of the most annoying moppets to ever step in front of a camera. The most abominable of the bunch is Janie, whose delivery of “not a smitch of temperature” just about sends the cathartic finale careening into a ditch.

 
14 of 25

Benjamin Braddock

Benjamin Braddock
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Baby Boomer hero Benjamin Braddock (Dustin Hoffman) is far more sympathetic in the first half of Mike Nichols’ landmark film when he’s lazing around his parents’ pool and engaging in a meaningless affair with Mrs. Robinson (Anne Bancroft). However, once he decides he has feelings for the Robinsons’ daughter, Elaine (Katharine Ross), Benjamin turns into a deeply creepy stalker who won’t leave the poor girl alone until she believes his version of events with regards to her mother. Thematically, it all works as it’s supposed to, but by the end of the film, on a personal level, we want nothing more to do with this privileged jerk.

 
15 of 25

John Bender

John Bender
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John Hughes’ teenaged heroes, particularly the dudes, are all full of s**t, but Judd Nelson’s rebellious blowhard in “The Breakfast Club” is spilling over with the stuff. Every single character in the film is a self-pitying mess, but Bender, who’s positioned as the film’s truth-teller due to his wrong-side-of-the-tracks upbringing, is impossible to take. He’s a bully. He browbeats and slūt-shames Claire. Yet he gets to claim fist-pumping victory for the group’s climactic epiphany. 

 
16 of 25

Max (Put Into Space by Jinx)

Max (Put Into Space by Jinx)
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Lil’ Leaf Phoenix (soon to be Joaquin) was a lovable rascal in lots of mid-1980s programs (“Russkies”, for example!), but there’s nothing remotely adorable about him in “SpaceCamp," where his incessant whining convinces a psychotic robot to turn a simulated shuttle launch into a perilously real one. Max turns out to be helpful in the retrieval of emergency oxygen tanks, but let’s be real: This near-tragedy never had to happen, and it’s 100 percent Max’s fault.

 
17 of 25

Lester Burnham

Lester Burnham
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Possibly the most insufferable fictional character of the last 20 years, Lester Burnham (Kevin Spacey) is a frustrated suburban father who hates his job, his wife (Annette Bening) and seems on the fence about his daughter (Thora Birch). He impetuously reverts to his teen years by taking a job at a fast food joint, buying weed from the teenager next door and, most disturbingly, fantasizing about his daughter’s best friend ( Mena Suvari). There’s a sharply satirical component to Alan Ball’s screenplay, but the film goes gooey at the end. Mendes wants us to sympathize with Burnham, but aside from  not having sex with a teenager, the character has done nothing to earn it. 

 
18 of 25

Leslie Zevo

Leslie Zevo
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Barry Levinson and Valerie Curtin had their hearts in the right place when they wrote this whimsical screenplay about a toymaker’s son fighting back against the family business’ embrace of war-based playthings. It’s an inventively designed film (by Ferdinando Scarfiotti), but the story gets lost in the Magritte-inspired sets. The biggest problem, however, is the main character, Leslie Zevo (Robin Williams), who’s meant to be a good-hearted naïf but is basically just Robin Williams doing his usual string-of-consciousness shtick. What worked for Levinson and Williams in “Good Morning, Vietnam” proves to be completely ill-suited to this material. Leslie needs another dimension besides doing a mean Ed Sullivan impersonation, and it’s just not there.

 
19 of 25

Trent

Trent
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Vince Vaughn’s Trent is essentially a horned-up Jiminy Cricket to Jon Favreau’s Mike. He wants for his friend’s happiness (as long as he can get lāid along the way) and believes he’s steering him in the correct direction — to Las Vegas, the Dresden, The Derby, and so on. He’s obnoxious, kinda racist (“Is he clean, Mikey?”) and treats women like dirt (e.g. making a show of shredding the phone number of the girl he just met). He jumps up on a table at The 101 Coffee Shop and thinks it’s cute. Trent’s the guy you grow out of when you hit 30. Hopefully.

 
20 of 25

Melanie Ralston

Melanie Ralston
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As long as she’s lounging on Ordell Robbie’s (Samuel L. Jackson) couch smoking weed, Melanie’s (Bridget Fonda) a pretty chill girl. However, bring her along on a job when you’re too addled to remember where you parked the car, and you’ve got trouble. How Louis (Robert De Niro) chooses to deal with this particular headache is a tad extreme,  but she absolutely redlines his agitation. Perhaps a sternly worded would've done the trick.

 
21 of 25

Jean Cabot

Jean Cabot
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Paul Haggis’ low-IQ Robert Altman homage hits its nadir with Sandra Bullock’s Jean Cabot. She’s the miserable, cartoonishly racist wife of the district attorney (Brendan Fraser), and when she’s carjacked her bigotry goes into overdrive. There are definitely people like Jean in the world, but they’re unlikely to do a philosophical U-turn just because they fell down the stairs.

 
22 of 25

Lester

Lester
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“If it bends, it’s funny. If it breaks, it’s not funny.” Woody Allen’s best Bergman riff draws most of its mirth from Alan Alda’s portrayal of an arrogant sitcom producer who’s convinced he’s pioneered comedy writing. Allen plays a frustrated documentarian who agrees to shoot a PBS special celebrating Alda’s craft, and he winds up sabotaging it out of personal spite. As Lester’s absurd claims pile up, you can’t blame him.

 
23 of 25

Barry Judd

Barry Judd
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“I can’t fire them. I hired these guys for three days a week, and they just started showing up every day. That was four years ago.” John Cusack’s Rob Gordon brought the blight of Barry Judd on himself. A know-it-all vinyl head prone to segueing from Katrina and the Waves to Mitch Ryder and the Detroit Wheels, Barry knows where Rob’s last nerve resides, and he hops on it with no mercy. In his calmer moments, he’s a genuinely educated music fan who loves to chop it up; alas, he’s also the type of guy who believes in the purity of his opinion and will brook no disagreement. He’s the reason people don’t go to record stores.

 
24 of 25

Will Hunting

Will Hunting
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Will Hunting doesn’t exist. He’s a fantasy concocted by two reasonably well-read Bostonites who loathed the Harvard jerks they encountered during their youth. The idea of a prodigious math mind escaping the drudgery of his anti-intellectual environs is pretty spiffy, but once Will trots out Howard Zinn’s “A People’s History of the United States” to defend his authoritative read on the country’s ills, you’re ready to move on.

 
25 of 25

Ruby Rhod

Ruby Rhod
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Chris Tucker catches way too much grief. His rapid-fire, high-pitched delivery is grating only when he’s not engaged with the material. In films like “Money Talks," “Rush Hour” and “Jackie Brown," he’s a showstopping delight; he’s one of the few comedic superstars of the last two decades who could make a claim to being in Eddie Murphy’s area code. What you cannot do with Tucker, however, is give him free rein, which is what Luc Besson did in “The Fifth Sense." It’s a little bit Michael Jackson, a little bit Prince and a whole lot of awful.

Jeremy Smith is a freelance entertainment writer and the author of "George Clooney: Anatomy of an Actor". His second book, "When It Was Cool", is due out in 2021.

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