1. Hedra ‘Hedy’ Carlson: Single White Female (1992)
Before Craigslist, there was the “classifieds” section of the newspaper. And before The Roommate, there was Single White Female. It’s the story of Allie Jones (Bridget Fonda), a burgeoning software developer in New York City who splits with her fiancé (Steven Weber) after discovering he slept with his ex-wife. Not wanting to live alone, she takes out an ad seeking a roommate, and eventually settles on the shy Hedy Carlson (Jennifer Jason Leigh). The two start off as friends, but Hedy engages in some shady behavior–erasing Allie’s ex’s conciliatory messages, and emulating her dress. It’s all just odd albeit harmless behavior to Allie until she gets back together with her fiancé, and Hedy’s obsessive jealousy goes into overdrive. She kills the puppy she gave Allie, dyes/styles her hair to look just like Allie, and performs oral sex on Allie’s fiancé while he’s half-asleep—tricking him into thinking she’s Allie—eventually killing him with a stiletto. According to film critic Roger Ebert, “She is played by Jennifer Jason Leigh as a sweet-faced, friendly little innocent. Those are the ones you have to look out for. I cannot find "hedra" in my unabridged dictionary, and yet somehow the name teases me. Surely it is the name of a mythological beast? One with a rent receipt in one hand and a kitchen knife in the other?”
2. David McCall: Fear (1996)
Nicole Walker (Reese Witherspoon) is a virginal, rebellious teen who lives with her overbearing father, Steven ( CSI’s William Petersen), stepmother, and little brother. One night, she meets David McCall (Mark Wahlberg) at a rave, and is immediately drawn to his soft-spoken, terribly polite personality. Pretty soon, the two are all lovey-dovey, going on romantic carnival rides set to an ethereal cover of The Rolling Stones’ “Wild Horses.” But something is rotten in Denmark. After sleeping with Nicole, David begins to show signs of, well, being a psycho—shoving her friend to the ground and taunting Nicole’s father about taking her virginity: “See, I'm hip to your problems. All of 'em. I know you abandoned Nicole when she needed you most... 'cause I licked her sweet tears.” David even punches himself repeatedly in the chest, and then blames the beating on Nicole’s father. Eventually, Nicole witnesses David sexually assaulting her best friend (Alyssa Milano), and breaks up with him. Then he really loses it. Steven finds a shrine built for Nicole in David’s house, complete with doctored pictures of Nicole’s family—replacing Steven’s head with David’s—a pair of Nicole’s panties, etc. Then, David carves Nicole’s name into his chest, and finally, engages in a home invasion where he decapitates the family dog. The lesson being, ladies: don’t get picked up by guys at raves.
3. Annie Wilkes: Misery (1990)
Biebermania, this is not. Based on the Stephen King novel of the same name and directed by Rob Reiner, Misery centers on famed romance novelist Paul Shedon (James Caan), best known for his series of novels starring fictional Misery Chastain. When he’s caught in a blizzard, he crashes his car, and is rescued by a nurse, Annie Wilkes (Kathy Bates), who brings him to her secluded home. Paul’s legs are broken and his shoulder is dislocated, leaving him bedridden. Annie soon reveals that she is Paul’s No. 1 fan, gushing about his Misery novels. However, when she reads his latest, Misery’s Child, and learns that he’s killed off Misery, she goes ballistic—attempting to smash a table over his head, then locking him in his room. Yes, Annie is a complete psychopath; she’s a cross of Bette Davis’ obsessive fan in All About Eve and Nurse Ratched in One Flew Over the Cuckoo’s Nest. She burns the manuscript to Paul’s book, insisting he write a new one called Misery’s Return, and, after several escape attempts by Paul, “hobbles” him by smashing his ankles with a sledgehammer.
4. Buck O’Brien: Chuck & Buck (2000)
Buck O’Brien (Mike White, who also wrote the film) is in a state of arrested development. He’s a soft-spoken 27-year-old loner who lives with his mother, and, when he’s not sucking on lollipops, is an amateur playwright. When Buck’s mother dies, he invites his childhood friend, Chuck (Chris Weitz), to the funeral. Chuck—or Charlie, as everyone calls him now—is a successful music exec with a fiancée. However, Buck is convinced that Chuck & Buck had sexual relations when they were 11, and, although Chuck has repressed these memories, Buck hasn’t developed much at all since they occurred. After Buck’s sexual advances get shot down, Chuck, trying to be a good friend—or is it something more?—invites Buck out to visit him in L.A. Buck immediately empties his bank account, shacks up in a shady L.A. motel, and slowly tries to incorporate himself into Chuck’s life—first stalking him at his office, before finally working up the nerve to confront Chuck and his fiancée in person. When Buck is invited to—and feels alienated during—a promotion party at Chuck’s home, he realizes that the two are at very different stages in life, and his obsession intensifies. The contrast between White, a goofy-faced, freckled, pouty adult, and Weitz, a Tom Cruise-type, provides a fascinating juxtaposition, and the film also provides a noteworthy commentary on how these actions—phone hang-ups, following someone to a mall, etc.—are completely acceptable when done by a teenage boy, but when it’s done by an adult, it’s considered downright creepy (and illegal).
5. Max Cady: Cape Fear (1991)
Robert De Niro is no stranger to stalking, and will make an appearance later on this list (and no, it’s not for Taxi Driver, either). Although Martin Scorsese’s remake pales in comparison to the 1962 Robert Mitchum-starrer, Robert De Niro’s wacko performance—with his heavily tattooed body and exaggerated southern accent—takes the cake. Fourteen years ago, Cady was being tried for the rape and battery of a young woman, and his public defender, Sam Bowden (Nick Nolte), was so appalled by the nature of the crime that he kept hidden from the court a note that would have lightened Cady’s sentence, or even had him acquitted. Now that Cady is out of jail, he sets his sights on Bowden. First, he poisons the family dog, and then, he picks up Cady’s colleague at a bar, goes to her house, and then proceeds to break her arm, bite a chunk of flesh out of her cheek, and brutally beat and rape her. Then, he targets Bowden’s wife (Jessica Lange) and teenage daughter (Juliette Lewis). In one of the film’s creepiest scenes, Cady disguises himself as the girl’s drama teacher, and kisses her. “Cown-seh-lerrrrr!”
6. Alex Forrest: Fatal Attraction (1987)
Michael Douglas sure knows how to pick ‘em. He’s been sexually assaulted by Demi Moore in Disclosure; fallen for a serial killer in Basic Instinct; and his lovely wife cheated on him with a sexy painter in A Perfect Murder. But his tryst with Alex Forrest (Glenn Close) is what started it all. Dan Gallagher (Douglas) has a weekend affair with Forrest while his wife and daughter are out of town. He thinks the fling is kaput, even though Alex threatens suicide when he leaves. Then, she stalks him at his office, and calls him at home, claiming she’s pregnant and is keeping their baby. When Dan finally confronts her, she famously says, “I’m not going to be ignored, Dan!” After Dan moves the family to upstate New York, Alex follows—pouring acid on his car, boiling their pet rabbit, before finally kidnapping the daughter and attempting to kill Dan, and then his wife, with a steak knife. Fellas, don’t cheat on your wives. It’ll always come back to bite—or stab—you in the ass.
7. Martin Burney: Sleeping With the Enemy (1991)
1991 was truly “the year of the stalker.” You had Cape Fear, the scissor-wielding man-child in Kenneth Branagh’s underrated neo-noir, Dead Again, Silence of the Lambs, and, last but not least, Sleeping With the Enemy. The film centers on Laura Burney (Julia Roberts), a woman who marries the passionate, handsome, and wealthy investment counselor Martin Burney (Patrick Bergin). However, it’s soon revealed that he has violent OCD—first yelling at Laura when the towels in their Cape Cod summer home aren’t perfectly aligned, to eventually beating and raping her for the most minor of tidiness-related transgressions. Laura, tricking her husband into thinking she can’t swim, fakes her drowning, and starts a new life in Cedar Falls, Iowa, and falling for a kind drama teacher. However, Martin eventually tracks her down, and, after taunting her by leaving a series of clues around the house, confronts his battered wife, brandishing a gun and threatening to kill her new love. “I can't live without you. And I won't let you live without me,” he says. However, Laura gets control of Martin’s gun, and, in bad-ass fashion, calls the police, saying, “Come quickly, I’ve just killed an intruder,” before putting three bullets in his chest.
8. Peyton Flanders: The Hand That Rocks the Cradle (1992)
Hell hath no fury like a… you get the picture. Before his masterpiece L.A. Confidential, director Curtis Hanson specialized in sleazy B-movies like Bad Influence, and the piece de resistance, The Hand That Rocks the Cradle. Claire Bartel (Annabella Sciorra) is mother to little Emma (Madeline Zima), and pregnant with her second child. However, during a routine checkup, her obstetrician, Dr. Mott, molests her. She presses charges, and, after several other women come forward with similar allegations, he commits suicide—leaving his pregnant wife (Rebecca De Mornay), a widow. After learning that she’s left with no money following the suicide, she suffers a terrible hemorrhage, losing her baby. In an act of revenge, she targets Claire’s family, who, in need of a nanny after Claire gives birth to a young son, hire her for the job under the pseudonym “Peyton Flanders.” Peyton immediately attempts to take Claire’s place, breastfeeding her son—causing him to hate his mother’s milk—framing their mentally retarded caretaker (Ernie Hudson) by planting a pair of the daughter’s panties among his things, and coming onto Claire’s husband while trying to convince Claire that he’s having an affair with his friend, Marlene (Julianne Moore). The lesson here being: don’t ever hire a sexy nanny.
9. Rupert Pupkin: The King of Comedy (1983)
Well ahead of its time, Martin Scorsese’s social commentary on celebrity stalking was a box office bomb, grossing just over $2 million worldwide. However, the story of Rupert Pupkin (Robert De Niro), a starfucker and aspiring-delusional stand-up comic, has since been recognized as a classic. After a chance encounter with Jerry Langford (Jerry Lewis), a celebrated comedian and talk show host in the Johnny Carson mold Rupert believes he’s on the cusp of achieving greatness. He engages in strange, delusional fantasies in the basement of his home—where he still lives with his mother—acting out the show with cardboard cutouts of Langford and Co. Following a series of rejections by his agents, and then Langford himself, Pupkin, along with another stalker, Masha (Sandra Bernhard), kidnaps Langford and ties him to a chair in Masha’s parents’ Manhattan townhouse, demanding to the FBI and the authorities that he be given an opening stand-up comedy spot on Langford’s show. The authorities acquiesce, and Rupert actually is a hit, ending his applause-filled set with the famous confession: “Right now, Jerry is strapped to a chair... somewhere in the middle of the city. Go ahead, laugh. Thank you. I appreciate it. But the fact is, I'm here. Now, tomorrow you'll know I wasn't kidding... and you'll think I was crazy. But, look, I figure it this way. Better to be king for a night than schmuck for a lifetime. Thank you.”
10. Evelyn Draper: Play Misty For Me (1971)
Before her remarkable performance as the snobby, neglectful mother on the cult TV series Arrested Development, Jessica Walter was best known for her convincing turn as a crazed stalker in this, Clint Eastwood’s directorial debut. Evelyn Draper (Walter) calls in regularly to Dave Garver’s (Eastwood) California radio station requesting “Misty,” the classic Erroll Garner ballad. One evening, the two meet at a bar and Evelyn convinces Dave to have what she insists is no-strings sex with her. Not. The next day, she arrives at his home with lunch, and when Dave tries to patch things up with his more pure former flame, Tobie (Donna Mills), Evelyn completely loses it. She keeps popping up at Dave’s house uninvited, saying creepy things like, “Do you know your nostrils flare out into little wings when you're mad? It's kinda cute.” She ruins a business meeting between Dave and another woman, and then threatens to commit suicide at Dave’s home. Before long, she assumes a new identity and becomes Tobie’s roommate, and, wielding a pair of scissors, screams, “I hope Dave likes what he sees when he gets here. Because that's what he's taking to Hell with him!” before chopping off Tobie’s hair and tying her to a chair.
11. Barbara Covett: Notes on a Scandal (2006)
Like The Talented Mr. Ripley, there’s an intriguing undercurrent of homoeroticism in Barbara Covett’s (Judi Dench) fascination with the new teacher in school, Sheba Hart (Cate Blanchett). The two immediately strike up a friendship, with the old spinster writing in her diary that Sheba “may be the one.” However, when Barbara learns that Sheba is having an affair with one of her 15-year-old students—and refuses to end it—she ends up blackmailing Sheba, ultimately spreading the rumor around school of her crime. A scandal erupts, and Sheba is fired from her job and her husband (Bill Nighy) kicks her out of the house. “There was a magnificent opportunity here,” says Barbara in voiceover. “With stealth, I might secure the prize long-term, forever in my debt. I could gain everything by doing nothing.” With nowhere left to go, Sheba, thinking the boy confessed the affair to his mother, turns to Barbara, and stays at her home. When she finds Barbara’s diary, revealing not only that the crazy old kook revealed her secret, but also has sexual feelings for her, she confronts her, to which Barbara replies, “I gave you EXACTLY what you wanted! You'd still be stuck in that marriage without me!” Sheba says she could receive two years in prison, and Barbara, still delusional, responds, “They'll fly by! I'll visit you every week! We've so much life to live together!”
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Marlow Stern works for The Daily Beast and has a master's from the Columbia University Graduate School of Journalism. He has served in the editorial department of Blender magazine, as an editor at Amplifier magazine, and, since 2007, editor of Manhattan Movie Magazine.