40. The Terminator
Played by Arnold Schwarzenegger in The Terminator (1984, dir. James Cameron) and two later films

Before The Terminator, Schwarzenegger was viewed as little more than a B-list barbarian. But Cameron helped turn his shortcomings into strengths. Not the most expressive actor? Doesn’t matter; he’s a robot. Can’t really pronounce the name “Sarah Connor”? So what? This cyborg lets his muscles do the talking. But seriously—give the newly minted governor the credit he’s due. His intensely singular performance as the killing machine that can’t be reasoned with blew us away in the first film. And in the franchise’s second installment, audiences were surprised to discover that the tin man really does have a heart.

Defining Moment: The “I’ll be back” slaughter scene at the police station is the obvious choice. But a more deserving moment might be when the Terminator takes a scalpel to his own skin in a skanky motel room. After popping out his left eyeball, he stares in the mirror. One mechanical pupil glows a ghastly red. (MGM DVD)

39. Michael Dorsey/Dorothy Michaels
Played by Dustin Hoffman in Tootsie (1982, dir. Sydney Pollack)

There has been plenty of famous drag in Hollywood, from Some Like It Hot to Mrs. Doubtfire, but Hoffman’s dual gig as Michael Dorsey, unemployed New Yawk actor, and Dorothy Michaels, popular matronly soap star, resonates loudest with contemporary audiences. With four Oscar nominations (and one win) already to his credit, Hoffman had more than proven his chops by then; but this drama-comedy, male-female dichotomy of a film was something else again. Hoffman based his portrayal of Dorothy largely on his mother (“She’s the heart of Tootsie,” he has said)—but he had a little more specialized help as well: Andy Warhol “superstar” Holly Woodlawn (née Harold Ajzenberg) was hired to teach him the finer points of lipstick and pantyhose.

Defining Moment: His improvised on-air confession, of sorts—“But . . . as a woman!” (Columbia TriStar DVD)

38. Willy Wonka
Played by Gene Wilder in Willy Wonka & the Chocolate Factory (1971, dir. Mel Stuart)

He’s Oscar Wilde on a sugar high, from his sparkling aphorisms to his velvet jacket to his glucose-infused factory. “Every kid asks me if the sets were made of real candy,” says Wilder. “Everything you could suck on was real, except when I ate that cup of tea. That was wax.” Willy is the father that Charlie never had. “I’m a magician, a carnival barker,” says Wilder. “I’m all those things to impress the children.” But his psychedelic factory tour is a sugary version of Dante’s inferno. And all the children get their just desserts.

Defining Moment: Wilder dreamed up Willy’s whimsical entrance and made it a condition of his doing the role. After limping down a red carpet, he drops his cane, teeters precariously, and then—to the delight and astonishment of all—executes a perfect somersault. “I wanted that to be a question mark from the beginning—whether I was lying or telling the truth. Otherwise, it was like corned beef on white bread.” (Warner DVD)

37. Jake Gittes
Played by Jack Nicholson in Chinatown (1974, dir. Roman Polanski) and one later film

From our first glimpse of Jake Gittes—a private detective who looks infinitely bored and yet oddly vulnerable—we know we’re in a film that honors the noir tradition as epitomized by Bogart’s Sam Spade. Gittes’s features resist softening into anything more compromising than a snarl, and though sliced (his bandaged nose is clownish but unfunny), beaten, and menaced, he refuses to buckle. Faye Dunaway quivers, John Huston looms, but Nicholson’s Gittes seems untouchable inside—until his last stricken moments onscreen.

Defining Moment: A crafty, tough operator who will cheat a cheating world without a blink (with a fake cough, he tears a page from a city ledger), he uses an ethnic slur to hoodwink a nursing home’s oily director. P.S. Don’t insult him during his morning shave. (Paramount DVD)

36. Alex Forrest
Played by Glenn Close in Fatal Attraction (1987, dir. Adrian Lyne)

Ah, the extramarital affair. Long lunches . . . short late-night phone calls . . . and no strings! Then came Alex Forrest, and life changed for cheatin’ men. Dan (Michael Douglas) is a lawyer with a gorgeous wife (Anne Archer) and an impish daughter. After a weekend fling with Alex, he expects to return to his world unscathed. Alex expects a lot more. Watching her stalk Dan made a generation of men think twice before straying and the same generation of women hesitate before going all “fatal attraction” on someone’s ass.

Defining Moment: When Dan prepares to leave in the morning, an emotionally and physically exposed (she’s bare-breasted) Alex begs him to stay. “I thought we’d have a good time,” he says. “No, you didn’t,” she replies. “You thought you’d have a good time. You didn’t stop for a second to think about me.” And you know what? She’s got a point. (Paramount DVD)

35. Dr. Evil
Played by Mike Myers in Austin Powers: International Man of Mystery (1997, dir. Jay Roach) and two later films

Myers threw us all a frickin’ bone when he created Austin’s pinky-gesturing, lip-pursing, Mr. Bigglesworth–stroking nemesis. The hilarious, nefarious doctor (don’t call him mister—he didn’t spend six years in evil medical school for that) is a delightfully creepy combination of You Only Live Twice baddie Ernst Stavro Blofeld and Saturday Night Live honcho Lorne Michaels. He’s queasily endearing in his lame malevolence—attempting the Macarena, reminiscing about his childhood summers in Rangoon, kvelling over Mini-Me, and, of course . . .

Defining Moment: Unfrozen after 30 years, Dr. Evil reveals to his staff his plans for dominating the planet: “We shall hold the world ransom for . . . one million dollars!!” (New Line DVD)

34. Bonnie Parker
Played by Faye Dunaway in Bonnie and Clyde (1967, dir. Arthur Penn)

Likes: adventure, poetry, gumption, Clyde Barrow. Dislikes: whiners, the law, hiding out, mortality. With her flaxen hair, black beret, and slender cigarettes, “the best damn
girl in Texas” is also the most glamorous, especially seen against the film’s Depression-era dust-bowl backdrop. Formerly a waitress, she better fits the profile of the beatific bank robber, who steals from the rich and pities the poor.

Defining Moment: After the gang captures a Texas Ranger, Bonnie decides to have a little fun with him. Suddenly “sweet as pie,” she kisses the humiliated captive smack on the lips for a picture that will later appear in newspapers across the state. (Warner DVD)

33. Ratso Rizzo
Played by Dustin Hoffman in Midnight Cowboy (1969, dir. John Schlesinger)

His name says it all: Ratso Rizzo is a New York City gutter-dweller. The sickly, down-and-out hustler spots easy prey in naive cowboy Joe Buck (Jon Voight), but soon he also finds a friend—and hope. The poor shmuck, he just wants to score the bus money to make it to Florida. But this is a story of dreams unfulfilled, and Hoffman’s pathetic street rat, both hilarious and heartbreakingly sad, becomes a kind of tragic hero.

Defining Moment: Ratso’s shrill wail, “I’m walkin’ here!” as he defiantly slaps the hood of an encroaching cab. Hoffman has said that not only was the line ad-libbed but the altercation was unplanned. Which doesn’t surprise us—it’s a true New York moment. (MGM DVD)

32. Holly Golightly
Played by Audrey Hepburn in Breakfast at Tiffany’s (1961, dir. Blake Edwards)

Tiffany’s. Givenchy. Holly Golightly. They go together like milk and a wineglass, coffee and a jar. Holly does seem to go lightly through life, picking up fifty dollars for the powder room and exclaiming “Quel rat!” about her benefactor in the cold morning light. But deep down, this glib party girl is too frightened even to buy furniture or give her cat a name. She wants to find a real-life place that makes her feel like Tiffany’s, where nothing bad could ever happen. Instead, she finds love.

Defining Moment: Vulnerable, wet, and frightened, Holly kisses Paul (George Peppard) in the pouring rain, sheltering Cat under her coat. (Paramount DVD)

31. Norma Desmond
Played by Gloria Swanson in Sunset Boulevard (1950, dir. Billy Wilder)

She’s the greatest star of them all, the faded queen of 1086 Sunset Boulevard. And despite her rants against talkies, this former silent film star delivers some of the greatest lines ever written: “I am big! It’s the pictures that got small!” and “Great stars have great pride.” Indeed. Swanson’s Desmond, running roughshod over her servant Max (her first director!) and gigolo hack Joe Gillis (William Holden), is a monomaniacal monster of the first stripe.

Defining Moment: Having ensured that Gillis is going to stay on her premises, Norma pulls herself together, as it were, and makes her final glitter-encrusted appearance: “All right, Mr. DeMille, I’m ready for my close-up.” (Paramount DVD)