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When Leading Men Go Bad

The most shocking villainous turns by our favorite movie stars

What makes a man turn bad? Philosophers have been debating this since debating began.

What makes a leading man turn bad? Ah, now we’re into easier territory.

Some actors simply want to stretch themselves. Others relish sinking their teeth into a juicy, bad-guy role.

But those moments when your favorite cinematic hero suddenly turns up evil and frightening tend to occur at the tail-end of a career, when the leading man’s options have either been reduced (because no one wants him for the hero anymore), or expanded (because he’s allowed roles beyond his no-longer-so-lucrative hero roles).

Take Kevin Costner. Sure, he’s delved into the dark side. Butch Haynes in “A Perfect World” is a classic anti-hero until the final reel, when we realize just how crazy he is. Costner’s Wyatt Earp is the darkest of our cinematic Wyatt Earps, while his Thomas J. Murphy is wholly, believably frightening in the otherwise worthless “3000 Miles to Graceland.” But playing a serial killer in “Mr. Brooks”? This is new territory, and it probably wouldn’t have happened if he were still a No. 1 box office attraction. That catch with Dad in an Iowa cornfield was a long time ago.

The following is a compilation of some of the more surprising villainous turns by our favorite leading men. I’ve tried to ignore anti-hero roles (“Bonnie and Clyde”), and actors whose white hat tends toward gray (Paul Newman, Brad Pitt) or black (Robert Mitchum, Robert De Niro). It’s no surprise, for example, when Jack Nicholson shows up all sinister. But these guys? Who thought they had it in ‘em?

8. Tom Hanks in "Road to Perdition"

OK, so I’m already breaking my rules. This isn’t a true villainous turn since Hanks’ Michael Sullivan, while an enforcer for John Rooney’s gang, is still the hero of the film. He’s a family man and a professional. Hell, he plays piano with his boss just as Hanks’ Josh did with his boss in “Big.”

But it’s on the list for two reasons. The first is Hanks’ rep as a real-life nice guy — which he once mocked on “Saturday Night Live” — along with the nice-guy roles he played in an unprecedented string of box-office smashes in the 1990s. Moviegoers just loved to love them some Tom Hanks, and that’s where the studios wanted to place their bets: on Hanks in another nice-guy role. So just playing a mob enforcer was a feat.

The better reason is contained in one scene in “Perdition.” After Michael’s son inadvertently witnesses John Rooney’s son (a frighteningly perfect Daniel Craig) killing another mobster, Michael is sent out on a last-minute job: to hand a note to jazz club owner Tony Calvino who’s “light again.” The beefy bouncer of the club is tough until Michael identifies himself; then he turns deferential and loquacious. He tells Michael his problems: How he’s a boxer by trade, how he’d make a pretty good bodyguard, and is Mr. Rooney looking for anyone? Michael says he’ll ask. A bond is established. Then they go into Mr. Calvino’s office.

Of course the note reads, “Kill Sullivan and all debts are paid.” It’s the note that propels the rest of the movie. But Michael, senses attuned to the irregular, kills Calvino first and then plugs the loquacious bouncer. Boom! Boom! Both go down. Here’s what I like: They could’ve easily made the bouncer a jerk, someone who deserved getting shot. Instead they made us like him, only to have Tom Hanks, of all people, shoot him in the head. In a sense it’s an announcement. There’s a new sheriff in town, and his name ain’t Woody.

7. Tom Cruise in “Magnolia”

Cruise is the biggest gray-hat on the list. From “Top Gun” to “War of the Worlds,” he’s less the hero we root for than the jerk we root for. He’s the guy we hope will overcome his obvious flaws. Sometimes he even plays outright villains: “Taps,” “Interview with the Vampire,” “Collateral.” An argument can be made he’s best playing villains.

You could also say his character in “Magnolia” isn’t a true villain. He doesn’t kill anyone. He doesn’t beat up anyone. In the end there’s a whiff of redemption.

Still: No romantic star has ever played a character as misogynistic as Frank T. J. Mackey, the creator of the “Seduce and Destroy” system of getting into women’s pants, the man at the other end of 1-877-TAME-HER. Most of what he says can’t even be printed here. In his presentations he struts across the stage in his leather vest, chest out, hair tied in that odd, samurai ponytail. He’s the locker room braggart writ large. He uses every pathetic dysphemism possible for the female anatomy. “Denise the piece,” he says. “You are going to give me that cherry pie, sweet momma baby.”

Here’s the irony: His chest-thumping calls to manhood are to be achieved through the very means many feel are un-manning men: i.e., womanly confession (“Thanks for sharing that with us, Geoff”), and office work (“Turn to your blue booklets”). It’s misogyny as big business. It’s brilliant.

The female interviewer slowly strips away Mackey’s facade. She catches him in lies. He came this close to getting his Masters? Actually he never enrolled in college. His father died, and his mother is still alive? Actually his mother died of cancer in 1980 — he cared for her as a teenager — while his father abandoned them both. His woman-hatred is really father-hatred. Caught, he stews in a petulant glower, the film’s ultimate lesson. He says the past doesn’t matter — “The most useless thing in the world is that which is behind me: Chapter Three” — but that’s self-help talk. As the narrator reminds us at the film’s close: “We may be through with the past, but the past ain’t through with us.”

6. Robin Williams in “One Hour Photo”

An argument can be made that Robin Williams’ performance as the stalker in “One Hour Photo” isn’t that different from his usual schmaltzy, family-friendly roles.

True, the manic Williams persona isn’t present. Here he plasters down his hair and personality. He’s quietly desperate. But even at the height of his popularity, even as he stood there basking in our laughter and applause, Williams always had a kind of quiet desperation in his face. He so wants to please. As does Sy, the photo guy.

Sy is the outsider who wants to unite with a family. How different is that from Williams’ role in “Mrs. Doubtfire”? He’ll go to hell and back to keep this family together. How different is that from Williams’ role in “What Dreams May Come”?

One can even look at Sy as yet another metaphor for the Hollywood filmmaker: the perfectionist whose boss (read: studio head) doesn’t care about his perfectionism, and who, despite this, wants to keep creating images of the perfect family. The movie is almost an indictment of the Hollywood system in general and Williams’ films in particular. The usual sentimentality about family is still present; it’s just embedded in the mind of a very sick man.

5. Tony Curtis in “The Boston Strangler”

For an actor with a lousy rep —nominated by Michael Medved as the worst actor of all time in “The Golden Turkey Awards” — Tony Curtis has given us some great performances. He played a racist con chained to Sidney Poitier in “The Defiant Ones,” a servile PR flak chained to Burt Lancaster’s gossip columnist in “Sweet Smell of Success” and a Roman slave chained to Laurence Olivier in “Spartacus.” Not to mention his comic turn as Joe/Josephine/Cary Grant in “Some Like It Hot.”

But for most of the 1960s he played glib roles in frothy sex comedies like “Sex and the Single Girl” and “The Great Race.”

The first shock in “The Boston Strangler” is that Curtis, as Albert DeSalvo, isn’t there for the first hour of the film. We see only his boots and gloved hands, and the results of his crimes. When he does show up, well, he ain’t pretty no more. He’s broken-nosed and fleshier of face. We see him commit one crime, then two. In a way this is more than he sees.

Once he’s apprehended (on a breaking-and-entering charge), we find out he’s a split personality — he doesn’t know what he does — so Henry Fonda, as head of the commission tracking him, tries to break through to the other side. Curtis scrunches in his chair like a chastened schoolboy. He twitches. He has flashes of memory in which Fonda, his interrogator, appears. The film was made at a time when Hollywood was still trying to cinematically recreate inner as well as outer journeys, and “Strangler” exhibits this best when DeSalvo feels his wife has betrayed him: He sees her, suddenly, as if from a long distance away. Later, confused and blinking, he says the idea of strangling her popped into his head, but “How did she know?” He doesn’t yet realize he did try to strangle her. He doesn’t yet realize his “ideas” are the Strangler’s actions.

In his book “Bambi vs. Godzilla,” David Mamet calls Curtis’ performance here, “Some of the greatest moments of film acting.”

Which leads to the inevitable question: Is Michael Medved right about anything?

4. Ronald Reagan in “The Killers”

What were they drinking on this set? And can the rest of us get some?

Excessive violence forced “The Killers,” the first two-hour, made-for-TV movie, into theaters in July 1964, but within two years its lead, Lee Marvin, would win the best actor Oscar for “Cat Ballou,” and its screenwriter, Gene L. Coon, would become writer and producer on that most iconic of TV shows, “Star Trek.” Its director, Don Siegel, would help create one of the most enduring film characters, “Dirty Harry,” while its hero, John Cassavetes, would become hero to independent filmmakers everywhere by directing “Faces,” “A Woman Under the Influence,” etc.

And then there’s Ronald Reagan. A week after the film’s release he was speaking at the 1964 Republican Convention. Two years later he was elected governor of California. Fourteen years after that he became president of the United States. These days, Republicans — and some Democrats — can’t go to the bathroom without invoking his name.

“The Killers” begins with the two title characters (Marvin and Clu Gulager) plugging ex-race car driver Johnny North (Cassavetes), who doesn’t try to run. This bothers Marvin. He also wonders about the $1 million heist North was involved in. So the killers follow his trail backwards while we get Johnny’s story: up-and-coming racer, involvement with a dame (Angie Dickinson), a crash that ends his career. Turns out she’s the dame of a small-time crime boss, Jack Browning (Reagan). When they need a driver for a heist, Johnny gets involved and seems to betray everyone. Actually he’s the one who’s betrayed, by the dame, which is also why he also doesn’t run when the killers come. In a way he’s already dead.

The great disconnect here, of course, is less because of Reagan’s movie career than what came after. How odd to see the President of the United States slap Angie Dickinson, get punched in the face by John Cassavetes, and, most disconcerting of all, shoot the killers from a nearby building with a high-powered telescopic rifle. Meanwhile, any rumors that Reagan is good in the role are greatly exaggerated. His means of conveying villainy amount to a) not smiling, and b) keeping one eyebrow raised for the length the film.

The correct rumor is that he didn’t want to play the villain. Apparently he saw himself in a different role.

3. Charlie Chaplin in “Monsieur Verdoux”

What’s shocking about “Monsieur Verdoux” isn’t that the most beloved comic actor in movie history plays a serial killer; it’s that he expects us to like this serial killer.

It’s the 1920s. Henri Verdoux (Chaplin), unable to find work after being discharged from his bank teller’s position, and with an invalid wife and curly-headed son to support, begins to charm old women into marrying him; then he kills them and takes their money.

The guy is prissy and particular, with a thin French moustache rather than Chaplin’s lower-class smudge (which Hitler ruined forever), but still we’re supposed to like him. Because he lost his job. Because he’s smart and philosophical and bemoans the misery of the world. Because he takes in stray cats and stray women (with stray cats).

Mostly, though, we’re supposed to like him because the women he kills are awful. The first onscreen victim, Lydia, is second-cousin to Edna Gulch: all black clothes and scowl. Martha Raye plays Annabella, the coarse, loud-mouthed victim he can’t kill (to comic effect). The Couvais family is made up of stupid bickerers. This is the film’s great, cowardly manipulation: Verdoux tries to kill no one you wouldn’t want dead.

At his trial, Verdoux excuses his murders by comparing them to the killing nations do —“As a mass killer, I’m an amateur by comparison,” he says — but beneath this argument lies a giant moral chasm. If the behavior of nations excused individual actions it’d be anything goes. Besides, 12 (13?) women are still dead. The film implies that they deserved dying, and maybe that’s the real shock of “Monsieur Verdoux.” We all have our untermenschen, and here, Chaplin, the great populist comic, unknowingly tells us his.

2. Harrison Ford in "What Lies Beneath"

Harrison Ford went from devil-may-care gunslinger (“Star Wars”) to stolid protector of other people’s families (“Witness”) to stolid protector of his own (the Jack Ryan movies), and in the process became the No. 1 box-office star in movie history. Sure, as a family man, he stumbled at times. Going crazy in Central America in “The Mosquito Coast.” Cheating on his wife in “Presumed Innocent.” But generally we knew he’d be there for us, as he was for Luke, Leia, Rachael, the Lapp family, and the sweet blessed memory of Helen Kimble. Remember that famous exchange in “The Fugitive”? “I didn’t kill my wife!” “I don’t care.”

“What Lies Beneath” plays off this image. The wife in this movie, Claire (Michelle Pfeiffer), feels there’s a ghost haunting their Vermont lake home. At first, she suspects her new neighbor of murder; then she feels she’s just going crazy. All the while Harrison plays distracted, hunky husband working on a “project” regarding “genetics” that will make him “famous.” Bit by bit, this facade crumbles. Seems there’s a missing co-ed. Seems he doesn’t know her. Then he admits he had an affair with her. Then he admits finding her dead in their home and disposing of the evidence. At 100 minutes in, we find out the truth: He — Han Solo, Indiana Jones, Jack Ryan — killed her to stop her from going to the Dean and ruining his career. Now he’s going to kill his wife, too.

Unfortunately, the movie quickly becomes cartoonish, mixing its Hitchcockian and supernatural elements, while Ford becomes another version of The Villain Who Won’t Stay Dead. Before the soggy end we’re having our own exchange with the former Dr. Richard Kimble: “I’m trying to kill my wife!” “We don’t care.”

1. Henry Fonda in "Once Upon a Time in the West"

He kills a family in cold blood. When a final family member turns up — a shocked, red-headed boy — he smiles before blowing the boy away, too. He mocks a cripple. He rapes a woman, matter-of-factly taunting her with her past (as a prostitute) and his past (as the murderer of her husband). We hear of the many men he’s killed, and we see in flashback how he sadistically hung one man on the shoulders of his younger brother, making the younger, in effect, responsible for the death of the older. He shoves a harmonica in the younger brother’s mouth as the boy struggles to keep his older brother alive. He gauges the world through the coldest blue eyes in movie history and sneers.

And yet. That slightly worried look. That light, almost mincing walk. That laconic Nebraska drawl. Tony Soprano may hold up Gary Cooper as the American hero but I’ll take Henry Fonda any day of the week. For decades he played guys like Abe Lincoln, Tom Joad, Wyatt Earp, Mister Roberts, Juror #8. For decades that Nebraskan drawl counseled empathy (“Wherever there’s a cop beating up a guy...”) and tolerance (“Prejudice always obscures the truth...”). Here? When Morton, the railroad baron, tells him it wasn’t necessary to kill the family, that he just wanted them scared, he replies, “People scare better when they’re dying.” And it’s the same voice. He makes his brutality sound logical. He makes it sound benevolent.

It’s like Auntie Em morphing into the Wicked Witch in “The Wizard of Oz.” In “Once Upon a Time,” Tom Joad morphed into Frank, the sadistic gunslinger, and audiences around the world shuddered.

The wish list

OK, so who should be playing bad? Here’s a quick list.

Morgan Freeman
He’s become our wisest supporting player, counselor to everyone from Jessica Tandy to Batman. He’s even played God. But he burst onto the scene as a Times Square pimp in 1987 in “Street Smart,” leading the mother of all critics, Pauline Kael, to ask, “Is Morgan Freeman the greatest American actor?” She thought he might be. Yes, he played a foul-mouthed hitman in “Nurse Betty,” but it would be fun to see him go bad again. Life ain’t all about the penguins.

Robert Redford
Unlike Paul Newman, Redford, once a star, hasn’t been interested in playing fallible anti-heroes or lovable bastards. He’s a taciturn, western hero, showing women the ropes. He’s a white hat. Time to put that craggy face to better use.

Bill Murray
It’s not often that I worry about a guy who has more money, success, women, and baseball teams than I could ever imagine, but I worry about Bill Murray. He’s like the Nathaniel Hawthorne short story, “The Birthmark,” about a man who removes a birthmark from his wife — her only imperfection — only to have her die. Perfection isn’t for this world. Bill Murray, meanwhile, has been trying to drain his comedy away for years but in the process his performances have become almost lifeless. Did you see “Broken Flowers”? Maybe a juicy villain role can keep Bill Murray from disappearing forever.

George Clooney
Sexiest man alive. The modern Cary Grant. But remember how good he was as the villain in “From Dusk Til Dawn”? Why not the sexiest villain alive?

John Cusack
Who couldn’t love that face? He held that boom box in the air and made compilation tapes and skated at Rockefeller Center and love dogs. But that face is middle-aged now and beginning to sag and, damn, doesn’t that make you mad? Doesn’t that make you wanna get mean and scary? C’mon Lloyd Dobler, whaddaya got?

Will Smith
He’s the new Tom Hanks, the most likeable actor in the world, the guy who can turn a character study like “The Pursuit of Happyness” into a $300 million box office smash. But can he play a villain? One way to find out.

—Erik Lundegaard knows from villains, having played Horatio Handlebars in the Burroughs Elementary School production of “Nelly’s Fishy Fate.” This piece was originally published on MSNBC.com.