The Good, the Bad and the Just Plain Mean

This year, Clint Eastwood, at the age of 78, announced that he is retiring. From acting. "You always want to quit while you’re ahead. You don’t want to be like a fighter who stays too long in the ring," he said, echoing a boxing metaphor he used years earlier when he compared actors to boxers, telling a reporter, "One never knows how much longer one has."

Eastwood does intend to continue directing. "I’ve got no plans to stop making films," he stated. Early in his career, he started thinking about directing as a possibility should audiences tire of him onscreen. He wanted to direct an episode of his 1960s TV series "Rawhide" (below) and was promised the opportunity, which never arose due to differences between the show’s producers and the studio.

Flash-forward a number of decades, and time has indeed provided him with the opportunity to redefine himself as a talented director, to greater acclaim than he ever garnered for his acting. At an age when many are already retired, Eastwood hit his stride in his 60s and 70s, highly regarded for such sincere, yet often bleak, dramas as "Unforgiven," "Mystic River," "Million Dollar Baby," "Letters from Iwo Jima," and "Changeling," four-times Oscar-nominated as director and twice a winner (for "Unforgiven" and "Million Dollar Baby").

As of this writing, Eastwood’s final screen role was the widowed Korean War veteran in "Gran Torino" (above). Looking back at his acting career, we reflected on the number of bad guys he has dealt his inimitable style of justice to and came up with our list of the five most memorable villains. We’re not talking your garden-variety bad guy here. Oh no, these malevolent misfits are so maligned that their sociopathic evil transcends the global threats posted by the most megalomaniacal of Bond villains.

1. & 2. Gian Maria Volonte in "A Fistful of Dollars" and "For a Few Dollars More"

Milan-born Gian Maria Volonte graduated from the National Academy of Dramatic Art in the 1950s and established his reputation as an actor in an Italian television production of Dostoyevsky’s "The Idiot." He had appeared in a few low-budget movies in the early 1960s, but "A Fistful of Dollars" (1964), the first of director Sergio Leone’s so-called "Man with No Name" trilogy, was his first international part and his first role as a villain.

Volonte felt his stage experience was of little value in a western, and he initially struggled with his portrayal of Ramon Rojo, the vain and sadistic sibling in a family of outlaw brothers vying with a rival clan for control of a corrupt border town. "Leone told me to practice scowling a lot," Volonte later recalled. The director also added a leather "killing glove" to the actor’s wardrobe and gave him more menacing lines.

Leone deemed Volonte "the histrionic type, who theatricalizes everything." For "A Fistful of Dollars," "this shortcoming," according to the director, "proved helpful to me. It emphasized the character - a spoiled child." A spoiled child, yes, but an utterly amoral creature who personally oversees and delights in the wholesale massacres of American and Mexican soldiers, the merciless slaughter of the rival family, and the sadistic stomping of Clint Eastwood’s bounty-hunting character.

When the film was released in Italy, the producers attempted to present it as an American import by giving all the Europeans, in front of and behind the camera, Yankee-sounding pseudonyms in the credits. Sergio Leone became "Bob Robertson," and Volonte was credited as "John Wells."

In his biography of Clint Eastwood, author Richard Schickel called Volonte "a highly regarded stage actor and committed leftist on his way to a distinguished career in more politically conscientious films," including a starring role in the 1970 Academy Award winner for Best Foreign Language Film, "Investigation of a Citizen Above Suspicion" (below).

One director who worked with Volonte recalled, "He’s a leftist, as he never tires of telling you." Volonte reportedly spent a lot of time on location for "A Fistful of Dollars" reflecting about the politics of his situation, filming in fascist Francisco Franco’s Spain "in a miserable village in a bizarre film." He even tried, unsuccessfully, to engage Eastwood in discussions about Italian politics.

According to Volonte, it was next to impossible for a young actor at that time to reach a wide audience unless he appeared in films that appealed to what he termed the "monopolistic controllers of distribution" in Italy, and westerns offered a starting point. Not surprisingly, the actor didn’t hesitate to again play the villain, opposite Clint Eastwood, in director Leone’s sequel, "For a Few Dollars More" (1965).

Volonte’s character in the early versions of the script was not much more than an ordinary desperado called "Tombstone." Leone transformed the outlaw into "El Indio," a marijuana-smoking addict who kills in the thralls of withdrawal. The director took personal delight in the notion that drug use was taboo in cinema at the time, especially in westerns.

Volonte (who died in 1994, age 61) gave "full vent to an evil the deliriousness of which he only hinted at in ‘A Fistful of Dollars,’" according to Richard Schickel. "A full-scale psychopath, smoking dope, torturing insects, if anything happier murdering innocent bystanders than he is doing away with those who have actually wronged him, achieving a kind of dreamy peace only after he has killed."

Incidentally, Sergio Leone filmed his westerns without sound. The international cast would speak in their native languages, including Italian, Spanish, German, and, of course, English. All the ambient sound and sound effects were added later, just as all the dialogue would be re-dubbed. For domestic release, Eastwood, who kept extensive notes during production, re-recorded his own voice. Volonte, who didn’t speak English, was dubbed by Paul Frees, a renowned voice actor best known for his work as Disney’s Ludwig Von Drake and, for Jay Ward Productions, Boris Badenov. Frees also supplied the voices for the drunken Union officer at the battle for the bridge in Leone’s "The Good, the Bad and the Ugly" and Mr. Morton, the railroad tycoon in Leone’s "Once Upon a Time in the West."

3. Lee Van Cleef in "The Good, the Bad and the Ugly"

Sergio Leone originally considered Volonte for the role of the murderous trickster Tuco in "The Good, the Bad and the Ugly," the last installment in his "Man with No Name" trilogy starring Clint Eastwood, but decided that "we needed instead an actor who wouldn’t be quite such hard work." The part instead went to Eli Wallach, who handily stole the picture while having the time of his life. Despite the popular notion that Leone cast Wallach based on his lively portrayal of a Mexican bandit chief in "The Magnificent Seven," the director was actually inspired by the actor’s role of a dangerous but playful outlaw in the Cinerama epic "How the West Was Won."

For several years, Lee Van Cleef had been a dependable small-role player in Hollywood westerns, whose name, according to Richard Schickel, "usually low in the credits, caused a small, pleasurably anticipatory frisson among devotees of the genre," and whose characters rarely survived until the final reel. Iconically, it is a startling close-up of Van Cleef’s self-described "beady-eyed sneer" (below) that fills the screen in the opening shot of his first film, "High Noon" (1952).

Van Cleef went on to being killed with a knife by Kirk Douglas in "Gunfight at the OK Corral," getting gunned down by Gregory Peck in "The Bravados," and playing a moronic flunky of bad guy Lee Marvin’s in "The Man Who Shot Liberty Valance" (below). On an episode of "Rawhide," Van Cleef shot Eastwood off his horse before being properly dispatched.

By the early 1960s, his career was on the skids, due in part to a drinking problem he had recently overcome and to a serious knee injury from which he was recovering.

The role of bounty hunter Colonel Mortimer in "For a Few Dollars More," a genuinely sympathetic character who serves as a surrogate father for Clint Eastwood in their uneasy alliance to track down El Indio, was initially offered to Henry Fonda, but Leone couldn’t meet his salary. (Leone eventually could afford Fonda when he cast him as the cold-blooded gunfighter in "Once Upon a Time in the West.") The part of Mortimer was subsequently turned down by Jack Palance.

Van Cleef would have been the first to say that his career was rescued, if not completely reinvented, by the role of Colonel Mortimer (above), which led to several larger parts in the years ahead, on both sides of the Atlantic. He liked to say, "My story turned into a rags-to-riches story, and not a moment too soon."

For the role of the "Bad" in "The Good, the Bad and the Ugly," a chilling, gold-hungry fiend ironically called "Angel Eyes," Leone first approached Charles Bronson, who agreed but was bound by contract to appear in "The Dirty Dozen." (Like Fonda, Bronson would go on to costar in Leone’s "Once Upon a Time in the West.") Leone started thinking about Van Cleef again, the actor whom he had elevated to European stardom, but he worried that carrying over Van Cleef from "For a Few Dollars More" would garner criticism of the director copying himself. Leone, as well, wasn’t totally convinced of Van Cleef’s range as an actor. Leone later recalled, "I said to myself that Van Cleef had first played a romantic character in ‘For a Few Dollars More.’ The idea of getting him to play a character who was the opposite of that began to appeal to me."

Praise must be given to Van Cleef (who died, age 64, in 1989) for a transformation in characterization that is nothing short of remarkable. Colonel Mortimer and Angel Eyes may share a similar taste in wardrobe, but what was once a grandfatherly twinkle of the eye is now the icy glare of a predator. The former’s begrudging grin is turned into a grimace of soulless evil, punctuated by a hollow laugh.

4. Andy Robinson in "Dirty Harry"

Although it was made nearly 40 years ago, "Dirty Harry" remains one of the most popular among Clint Eastwood’s films, the one with which he is most often associated. As an unorthodox San Francisco cop who relentlessly pursues a serial killer called Scorpio (loosely based on the Zodiac Killer, who terrorized Northern California communities in the late 1960s), Eastwood unveiled an iconic portrait of an alienated lawman more interested in justice than regulations and the rights of criminals.

Director Don Siegel originally wanted Audie Murphy to portray Scorpio. Murphy, one of America’s most decorated soldiers of World War II (above), found unexpected success as the baby-faced star of several low-budget westerns throughout the 1950s into the ‘60s.

In 1970, Siegel, who had directed Murphy years earlier in a pair of B-movies, ran into the actor on a flight, and their ensuing conversation led Siegel to the realization, "My God, I’m looking for a killer and here’s the killer of all time, a war hero who killed over 250 people. He was a killer, though he didn’t look it. I thought it might be interesting. He had never really played a killer." In his biography of Murphy, author Don Graham noted, "Playing a psychopathic killer would have been the most radical departure in Audie’s acting career. At 2 percent of the gross, which is what Siegel was offering, Audie stood to make in the neighborhood of $600,000 for such a role." Sadly, Murphy died in a plane crash before "Dirty Harry" went into production.

Reportedly, Siegel also considered Rip Torn (best known for his Emmy Award-winning role of Artie on the HBO comedy series "The Larry Sanders Show") and Keir Dullea (star of "2001: A Space Odyssey") for the part of Scorpio before seeing a young actor named Andy Robinson in an Off-Broadway adaptation of Dostoyevsky’s "The Idiot," coincidentally, in the same role that boosted Gian Maria Volonte to stardom.

Robinson was trained at London’s Royal Academy of Dramatic Art on a Fullbright Scholarship. Prior to "Dirty Harry," he and Frederic Forrest played street punks on a 1968 episode of the TV series "N.Y.P.D." (not to be confused with "N.Y.P.D. Blue").

"Looking younger than his years and naturally soft-featured," Eastwood biographer Richard Schickel noted of Robinson, "he suggested infantile premortality and proposed evil as a kind of colic, rendering him helplessly restless, unplacably angry." Siegel himself admitted he cast Robinson because he had the face of "a choir boy."

In the film, Scorpio kills a woman swimming in a penthouse pool and demands a ransom of $100,000 from the mayor of San Francisco, otherwise threatening to kill an additional person per day. He shoots a ten-year-old boy in the face, threatens to murder a priest, tortures and buries alive a teenaged girl, has himself savagely beaten to frame Eastwood, and commandeers a school busload of terrified children.

Schickel commented, "Since this was the actor’s first movie, he had no image to defend, so there was an astonishing purity in his malice that suited the movie’s moral scheme perfectly. Not for a nanosecond does he suggest some mitigating explanation for his behavior."

In a 1996 interview that appeared in Psychotronic Video magazine, Robinson recalled working closely with the director to create the character. "Siegel and I put the Scorpio killer together bit by bit," he said. "And Don (Siegel) just let me wail." Robinson noted, "Siegel was the best. I learned more about filmmaking from him than all the other directors I’ve worked with, put together…It’s just a description of how knowledgeable he was, and of how willing he was to work with me, because it was a collaboration."

Robinson subsequently worked with Siegel again, in the 1973 crime thriller "Charley Varrick" and has remained a working actor in films, including "Mask," "Cobra," "Hellraiser," "Child’s Play 3" and "Pumpkinhead 2," although he once admitted, "Quite frankly, ‘Dirty Harry’ gave me a film career and ended it at the same time." According to the actor, "After we shot (‘Dirty Harry’), Siegel said, ‘Yeah, I ruined Robinson’s career.’"

"I was just picking up bits and pieces in various movies," Robinson said. "A lot of people in the business were frightened of me…I’m not exaggerating." In the wake of the initial release of "Dirty Harry," he received death threats while filmmakers balked at casting him in good guy roles. He was enjoying a two-year run portraying Frank Ryan on the daytime drama "Ryan’s Hope" - even garnering an Emmy nomination - when he suffered the humiliation of being replaced by another actor because producers were worried that having the guy who played the Scorpio killer in a lead role was disturbing viewers.

In the early 1990s, Robinson discovered newfound success in the recurring role of Garak the Cardassian on TV’s "Star Trek: Deep Space Nine" (above) and he directed a number of episodes of the series "Judging Amy" in the early 2000s.

5. John Malkovich in "In the Line of Fire"

There might be those who question the obvious omission of Gene Hackman’s portrayal of "Little" Bill Daggett in "Unforgiven" from our list of Clint Eastwood’s ultimate bad guys, but we view that sadistic lawman more as a corporate villain, not unlike the greedy land barons and their henchmen in "Joe Kidd," "High Plains Drifter" and "Pale Rider," not in the same league as the full-tilt psychopaths and sociopaths we’re honoring here.

"In the Line of Fire" (1993) was a noteworthy film for Eastwood on three counts. The $40 million budget made it the most expensive production in which he starred, it was not backed by his production company, Malpaso, and it was the last movie he would act in for a director other than himself, the exception here being Wolfgang Petersen, whose diverse résumé includes "Das Boot," "The Neverending Story," "The Perfect Storm" and "Troy."

Eastwood portrays a veteran Secret Service agent haunted by his failure to avert the assassination of President John F. Kennedy decades earlier. "Thrillers are as good as their villains," critic Roger Ebert observed, "and ‘In the Line of Fire’ has a great one - a clever, slimy creep who insidiously burrows his way into the psyche of the hero…The creep who likes to play mind games with his opponents, makes a series of phone calls" to Eastwood’s character, Frank, threatening to kill the current president.

The creep, a onetime CIA operative named Leary, is played to bone-chilling perfection by John Malkovich. In his biography of Clint Eastwood, Richard Schickel wrote, "Having honed his chops in Chicago’s Steppenwolf company (the prestigious theater company co-founded by actor Gary Sinise), he was an actor known for his bold, black, utterly unpredictable comic effects, which make his essential menace all the more terrifying. Adopting an absurdly languid manner, issuing his taunts and threats in a whispery drawl, he turns the movie into an aesthetic contest as well as a conflict between good and evil."

Critic Howard Hampton noted that Malkovich pushes Eastwood’s buttons "the same way ‘Dirty Harry’s’ Scorpio Killer pushed Harry’s (and the audience’s) only with far more elan and psychological sophistication. Malkovich has much better buttons at his disposal in terms of both script and acting technique than poor drooly Andy Robinson did."

Richard Schickel observed that the "striking resemblance" between Scorpio and Leary "contains a striking reversal. It is ‘In the Line of Fire’s’ heavy, not its hero, who finds himself victimized by a bureaucracy. As Leary points out, it was the CIA that made him…a perfectly poised, perfectly heartless killer, then turned him out when the Cold War thawed and it had no further use for the talents it conspired to create. There are, he says, no causes worth fighting for anymore. ‘All that’s left is the game,’ he tells Frank." Not surprisingly, Malkovich’s incomparable portrait of uncompromising evil earned him an Academy Award nomination for supporting actor.

In his review of the film, Roger Ebert wrote, "Eastwood is perfect for the role, as a man of long experience and deep feelings. He is set off by an inspired performance by Malkovich, who is quiet and methodical and very clever."

Eastwood, Malkovich said, reminded him of his father (an Eastwood fan himself), whom he described as a man of contradictions: "very elegant, very handsome, very strange and very self-contained; he was quite funny and had a bad temper." Richard Schickel proclaimed, "We are talking actor heaven here - the chance to project powerful, unresolved feelings onto a fellow player smart enough to encourage him."

Roger Ebert summed it up thus: "Most thrillers these days are about stunts and action. ‘In the Line of Fire’ has a mind."