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1963–1969: spaghetti Westerns and stardom

In late 1963, Eastwood's Rawhide co-star Eric Fleming rejected an offer to star in an Italian-made western called A Fistful of Dollars (1964), filmed in a remote region of Spain by a relatively unknown director, Sergio Leone. Richard Harrison suggested Eastwood to Leone because Harrison knew that Eastwood could play a cowboy convincingly. Eastwood thought the film would be an opportunity to escape from his Rawhide image. He signed a contract for $15,000 in wages for eleven weeks' work, with a bonus of a Mercedes-Benz automobile upon completion. Eastwood later said of the transition from a TV western to A Fistful of Dollars: "In Rawhide I did get awfully tired of playing the conventional white hat. The hero who kisses old ladies and dogs and was kind to everybody. I decided it was time to be an antihero." Eastwood was instrumental in creating the Man with No Name character's distinctive visual style and, although a non-smoker, Leone insisted Eastwood smoke cigars as an essential ingredient of the "mask" he was attempting to create for the character.

A Fistful of Dollars proved a landmark in the development of spaghetti Westerns, with Leone depicting a more lawless and desolate world than traditional westerns, and challenging American stereotypes of a western hero with a morally ambiguous antihero. The film's success made Eastwood a major star in Italy and he was rehired to star in For a Few Dollars More (1965), the second of the trilogy. Through the efforts of screenwriter Luciano Vincenzoni, the rights to For a Few Dollars More and the trilogy's final film, The Good, the Bad and the Ugly (1966), were sold to United Artists for about $900,000.

In January 1966, Eastwood met producer Dino De Laurentiis in New York City and agreed to star in a non-Western five-part anthology production, The Witches (Le Streghe, 1967), opposite De Laurentiis's wife, Silvana Mangano. Eastwood's 19-minute installment took only a few days to shoot, but his performance did not please critics; one wrote, "no other performance of his is quite so 'un-Clintlike'".

Two months later Eastwood began work on The Good, the Bad and the Ugly, again playing the mysterious Man with No Name. Lee Van Cleef returned as a ruthless fortune seeker, with Eli Wallach portraying the Mexican bandit Tuco Ramirez. The storyline involved the search for a cache of Confederate gold buried in a cemetery. During the filming of a scene in which a bridge was blown up, Eastwood urged Wallach to retreat to a hilltop. "I know about these things", he said. "Stay as far away from special effects and explosives as you can." Minutes later, confusion among the crew over the word "Vaya!" resulted in a premature explosion that could have killed Wallach.

I wanted to play it with an economy of words and create this whole feeling through attitude and movement. It was just the kind of character I had envisioned for a long time, keep to the mystery and allude to what happened in the past. It came about after the frustration of doing Rawhide for so long. I felt the less he said, the stronger he became and the more he grew in the imagination of the audience.

The Dollars trilogy was not released in the United States until 1967, when A Fistful of Dollars opened on January 18, followed by For a Few Dollars More on May 10, and The Good, the Bad and the Ugly on December 29. All three were commercially successful, particularly The Good, the Bad and the Ugly, which eventually earned $8 million in rental earnings and turned Eastwood into a major film star being ranked for the first time on Quigley's Top Ten Money Making Stars Poll in 1968 in fifth place. All three received poor reviews, and marked the beginning of a battle for Eastwood to win American film critics' respect. Judith Crist described A Fistful of Dollars as "cheapjack", while Newsweek called For a Few Dollars More "excruciatingly dopey". Renata Adler of The New York Times said The Good, the Bad and the Ugly was "the most expensive, pious and repellent movie in the history of its peculiar genre". Time magazine drew attention to the film's wooden acting, especially Eastwood's, though a few critics such as Vincent Canby and Bosley Crowther of The New York Times praised his coolness. Leone's cinematography was widely acclaimed, even by critics who disparaged the acting.

Stardom brought Eastwood more roles. He signed to star in the American revisionist western Hang 'Em High (1968) alongside Inger Stevens, Pat Hingle, Dennis Hopper, Ed Begley, Alan Hale Jr., Ben Johnson, Bruce Dern, and James MacArthur, playing a man who takes up a marshal 's badge and seeks revenge as a lawman after being lynched by vigilantes and left for dead. The film earned Eastwood $400,000 and 25% of its net box office. Using money earned from the Dollars trilogy, Eastwood's advisor Irving Leonard helped establish Eastwood's own production company, Malpaso Productions, named after Malpaso Creek on Eastwood's property in Monterey County, California. The 38-year-old actor was still relatively unknown as late as a month prior to the film's release, as evidenced by a July 1968 news item by syndicated columnist Dorothy Manners: "The proverbial man in the street is still asking, 'Who's Clint Eastwood? ' " Leonard arranged for Hang 'Em High to be a joint production with United Artists; when it opened in August, it had the largest opening weekend in United Artists' history. Hang 'Em High was widely praised by critics, including Archer Winsten of the New York Post, who called it "a western of quality, courage, danger and excitement".

Before Hang 'Em High ' s release, Eastwood had already begun working on Coogan's Bluff (1968), about an Arizona deputy sheriff tracking a wanted psychopathic criminal (Don Stroud) through New York City. He was reunited with Universal Studios for it after receiving an offer of $1 million – more than double his previous salary. Jennings Lang arranged for Eastwood to meet Don Siegel, a Universal contract director who later became Eastwood's close friend, forming a partnership that would last more than ten years and produce five films. Shooting began in November 1967, before the script had been finalized. The film was controversial for its portrayal of violence. Coogan's Bluff also became the first collaboration with Argentine composer Lalo Schifrin, who scored several Eastwood films in the 1970s and 1980s, including the Dirty Harry films.

Eastwood was paid $750,000 for the war epic Where Eagles Dare (1968), about a World War II squad parachuting into a Gestapo stronghold in the Alps. Richard Burton played the squad's commander, with Eastwood as his right-hand man. Eastwood was also cast as Two-Face in the Batman television show, but the series was canceled before filming began.

Eastwood then branched out to star in the only musical of his career, Paint Your Wagon (1969). Eastwood and Lee Marvin play gold miners who buy a Mormon settler's less favored wife (Jean Seberg) at an auction. Bad weather and delays plagued the production, and the film's budget eventually exceeded $20 million, which was high for the time. The film was not a critical or commercial success, but was nominated for a Golden Globe Award for Best Motion Picture – Musical or Comedy.