20. Detective Virgil Tibbs
Played by Sidney Poitier in In the Heat of the Night (1967, dir. Norman Jewison) and one later film

Made in the contradictory times when the Civil Rights Act was newly passed but so were the Watts riots, this Oscar-anointed drama hinges on proto-CSI detective Virgil Tibbs, stranded among the racist hicks of Sparta, Mississippi. His outrage is barely contained as he’s collared for a murder, then drafted into the investigation. He has no comment while every white cop around calls him “boy”; his steely glare and badge speak for him. Except once . . .

Defining Moment: When he tells the chief he’s got the wrong man, the chief sneers, “Virgil—that’s a funny name for a nigger boy from Philadelphia. What do they call you up there?” Unblinking,Virgil fires back, “They call me Mister Tibbs,” through clenched teeth. The indignation has echoed since. (MGM DVD)

19. Rick Blaine
Played by Humphrey Bogart in Casablanca (1942, dir. Michael Curtiz)

What separates Rick from other romantic male characters is that at the movie’s end, he doesn’t get the girl. But this is how he wants it. Well, not really—but he knows in his heart that his beloved Ilsa (Ingrid Bergman)’s staying with her husband is vital to winning the war. While Bogie wasn’t the studio’s first choice—George Raft was initially offered the part—his blend of tough-guy exterior and, as one character puts it, rank sentimentality gives Rick an air of street nobility, and lasting significance.

Defining Moment: After hearing of a young couple’s struggle to escape Casablanca, Rick allows the husband to win enough money at roulette to afford exit papers, and thereby spares the man’s wife from having to sleep with the shady Captain Renault, played by Claude Rains. (Warner DVD)

18. Carl Spackler
Played by Bill Murray in Caddyshack (1980, dir. Harold Ramis)

Was he stoned? Slow-witted? Suffering from too much Agent Orange? Who knows. But Murray’s insane, mumbled monologues cracked audiences up for the entire movie. His filthy, slack-jawed groundskeeper never did make sweet love to the grannies he stalked, nor could he kill that pesky dancing gopher. But thanks to a caddying gig with the Dalai Lama, he’ll still receive total consciousness on his deathbed. “So I got that going for me,” he says, “which is nice.”

Defining Moment: While “cannonballing” cheap wine and a Bob Marley–sized spliff with Chevy Chase’s Ty Webb, Spackler explains the benefits of the turf he invented, a cross between Kentucky Bluegrass, Featherbed Bent, and Northern California Sensimilla: “The amazing stuff about this is that you can play 36 holes on it in the afternoon, take it home, and just get stoned to the bejesus belt that night.” (Warner DVD)

17. Dorothy Gale
Played by Judy Garland in The Wizard of Oz (1939, dir. Victor Fleming)

This sweetly naive Kansas farmgirl is the prototypical dreamy adolescent—L. Frank Baum’s nod to every kid who ever felt like he or she didn’t belong. Dorothy is lost and lonely on her aunt’s monochromatic farm, but she’s even more out of place in the strange land of Oz—where she’s used by a wizard and hunted by a witch. Suddenly, Kansas and Auntie Em’s
warm embrace seem like home after all. No flying monkeys, for one thing.

Defining Moment: When Dorothy sings “Somewhere Over the Rainbow,” you can almost imagine a place where troubles melt like lemon drops. (Warner DVD)

16. Robin Hood
Played by Errol Flynn in The Adventures of Robin Hood (1938, dirs. Michael Curtiz and William Keighley)

Smirk all you want about merry men and green tights—out of all the embodiments of derring-do played by Flynn, his nobleman–turned–defender-of-the-poor-and-oppressed is the most purely joyous. And his spirit lives on—check out Legolas (Orlando Bloom) and that tusker in the climactic battle of The Lord of the Rings: The Return of the King.

Defining Moment: Crashing dinner with a dead deer on his back at Prince John’s place, inspiring the soon-to-be less-than-amused royal (Claude Rains) to call him “this saucy fellow.” (Warner DVD)

15. Hannibal Lecter
Played by Anthony Hopkins in The Silence of the Lambs (1991, dir. Jonathan Demme) and two later films

Brian Cox in Manhunter is less effete, for sure, but his Lecter isn’t the one you hear people imitating all the time, now is it? Hopkins’s portrayal of the world’s most urbane serial killer is a wonder of both actorly invention (he adapted the voice in part from Katharine Hepburn, with whom he had worked on The Lion in Winter) and villainous instinct.

Defining Moment: Of course, the death rattle after “Chianti.” (MGM DVD)

14. Randle Patrick McMurphy
Played by Jack Nicholson in One Flew Over the Cuckoo’s Nest (1975, dir. Milos Forman)

Nicholson’s manic and slightly corrosive charm motors this study of one roistering inmate’s effect on an entire mental institution. A statutory rapist who fakes insanity to leave the prison farm for the mental ward, McMurphy confronts Louise Fletcher’s repellent Nurse Ratched with momentarily glorious but ultimately tragic results.

Defining Moment: A clandestine boat trip (“You’re not a goddamn loony now, boy, you’re a fisherman!”) is his bravura scene. (Warner DVD)

13. Atticus Finch
Played by Gregory Peck in To Kill a Mockingbird (1962, dir. Robert Mulligan)

Peck won an Oscar for his layered, level-headed portrayal of a southern lawyer who defends a black man accused of rape, in this adaptation of Harper Lee’s classic novel. But beloved, bespectacled Atticus is noble in more ways than one: Recently widowed, he is also the tender father of two scrappy rascals, Jem and Scout. Though he’s never patronizing, there’s still nothing or no one he can’t explain.

Defining Moment: “Do you know what a compromise is?” Finch asks Scout, after she gets into a fight at school. “It’s an agreement reached by mutual consent.” It’s also a perfect example of Atticus-the-lawyer and Atticus-the-father meeting halfway. (Universal DVD)

12. Charles Foster Kane
Played by Orson Welles in Citizen Kane (1941, dir. Orson Welles)

The essential paradox here is that this movie is about a group of people delving into the character of the title newspaper magnate—who remains essentially unknowable. Sure, he’s rich, powerful, ambitious, contrary . . . but what’s he really all about? The sentimental pull of “Rosebud” aside, the answer may be uglier than anybody really wants to know.

Defining Moment: As his second wife, Susan Alexander Kane, prepares to leave him, Kane checkmates himself by saying to her, “You can’t do this to me.” In one unguarded moment he reveals the solipsism that will doom him to die alone. (Warner DVD)

11. Margo Channing
Played by Bette Davis in All About Eve (1950, dir. Joseph L. Mankiewicz)

This acid-tongued grande dame of the theatah gave us our first glimpse of malignant narcissism and neediness run amok—a phenomenon now referred to as the high-maintenance superstar. Ever vigilant to seize upon any perceived threat to her hegemony over the world’s affections and attention, Margo whips herself into a tantrum, alternately hurling barbs at her loyal supporters and bathing in her own bathos. And yet, for all her entitlement and self-destructive behavior, there’s something familiar and basic in her increasingly transparent desire to be loved despite, and not because of, her fame.

Defining Moment: When her jealous suspicions of her new acolyte boil over as party guests are scheduled to arrive, Margo concocts a brilliant mix of menace and self-mockery and lobs her legendary quip: “Fasten your seatbelts, it’s going to be a bumpy night.” (Fox DVD)