1980s

Main article: Clint Eastwood in the 1980s

In 1980, Eastwood directed and played the title role in Bronco Billy alongside Locke, Scatman Crothers, and Sam Bottoms.^[148] Eastwood has cited Bronco Billy as being one of the most relaxed shoots of his career and biographer Richard Schickel has argued that Bronco Billy is Eastwood's most self-referential character.^[149][150] The film was a rare commercial disappointment in Eastwood's career,^[151] but was liked by critics. Janet Maslin of The New York Times wrote that film was "...the best and funniest Clint Eastwood movie in quite a while", and praised Eastwood's directing, intricately juxtaposing the old West and the new West.^[152] Later that year, Eastwood starred in Any Which Way You Can, the sequel to Every Which Way But Loose. The film received a number of bad reviews from critics, although Maslin described it as "funnier and even better than its predecessor".^[151] Released over the Christmas season of 1980, Any Which Way You Can was a major box office success and ranked among the top five highest-grossing films of the year.^[153]

In 1981

In 1982, Eastwood directed and starred in Honkytonk Man, based on the eponymous Clancy Carlile's depression-era novel. Eastwood portrays a struggling western singer Red Stovall who suffers from tuberculosis, but has finally been given an opportunity to make it big at the Grand Ole Opry. He is accompanied by his young nephew (played by real-life son Kyle) to Nashville, Tennessee, where he is supposed to record a song. Only Time gave the film a good review in the United States, with most reviewers criticizing its blend of muted humor and tragedy.^[154] Nevertheless, the film received critical acclaim in France, where it was compared to John Ford's The Grapes of Wrath,^[155] and it has since acquired the very high rating of 93 percent on Rotten Tomatoes.^[156] In the same year Eastwood directed, produced, and starred in the Cold War-themed Firefox. Based on a 1977 novel with the same name written by Craig Thomas, the film was shot before but released after Honkeytonk Man. Russian filming locations were not possible due to the Cold War, and the film had to be shot in Vienna and other locations in Austria to simulate many of the Eurasian story locations. With a production cost of $20 million, it was Eastwood's highest budget film to date.^[157] People magazine likened Eastwood's performance to "Luke Skywalker trapped in Dirty Harry's Soul".^[157]
Eastwood directed and starred in the fourth Dirty Harry film, Sudden Impact, which was shot in the spring and summer of 1983 and is considered the darkest and most violent of the series.^[158] By this time Eastwood received 60 percent of all profits from films he starred in and directed, with the rest going to the studio.^[159] Sudden Impact was his final on-screen collaboration with Locke. She plays an artist who, along with her sister, was gang-raped a decade before the story takes place and seeks revenge for her sister's now-vegetative state by systematically murdering the rapists. The line "Go ahead, make my day" (uttered by Eastwood during an early scene in a coffee shop) has been cited as one of cinema's immortal lines. It was quoted by President Ronald Reagan in a speech to Congress, and used during the 1984 presidential elections.^{[160][161][162]} The film was the second most commercially successful of the Dirty Harry films, after The Enforcer, earning $70 million. It received very positive reviews, with many critics praising the feminist aspects of the film through its explorations of the physical and psychological consequences of rape.^[163]
Tightrope (1984) had Eastwood starring opposite Geneviève Bujold in a provocative thriller, inspired by newspaper articles about an elusive Bay Area rapist. Set in New Orleans to avoid confusion with the Dirty Harry films,^[164] Eastwood played a divorced cop drawn into his target's tortured psychology and fascination for sadomasochism.^[165] Tightrope was a critical and commercial hit and became the fourth highest-grossing R-rated film of 1984.^[166] Eastwood next starred in the crime comedy City Heat (1984) alongside Burt Reynolds, a film about a private eye and his partner who get mixed up with gangsters in the prohibition era of the 1930s. The film grossed around $50 million domestically, but was overshadowed by Eddie Murphy's Beverly Hills Cop.^[167]

Westerns. A period gone by, the pioneer, the loner operating by himself, without benefit of society. It usually has something to do with some sort of vengeance; he takes care of the vengeance himself, doesn't call the police. Like Robin Hood. It's the last masculine frontier. Romantic myth, I guess, though it's hard to think about anything romantic today. In a Western you can think, Jesus, there was a time when man was alone, on horseback, out there where man hasn't spoiled the land yet.

— Eastwood, on the philosophical allure of portraying western loners^[168]

Eastwood made his only foray into TV direction with the 1985 Amazing Stories episode Vanessa in the Garden, which starred Harvey Keitel and Locke. This was his first collaboration with Steven Spielberg, who later co-produced Flags of Our Fathers and Letters from Iwo Jima.^[169] He would revisit the Western genre when he directed and starred in Pale Rider (1985), a film based on the classic 1953 western Shane and follows a preacher descending from the mists of the Sierras to side with the miners during the California Gold Rush of 1850.^[170] The title is a reference to the Four Horsemen of the Apocalypse, as the rider of the pale horse is Death, and shows similarities to Eastwood's 1973 western High Plains Drifter in its themes of morality and justice as well as its exploration of the supernatural.^[171] Pale Rider became one of Eastwood's most successful films to date. It was hailed as one of the best films of 1985 and the best western to appear for a considerable period, with Gene Siskel of the Chicago Tribune remarking, "This year (1985) will go down in film history as the moment Clint Eastwood finally earned respect as an artist".^[172]
In 1986, Eastwood co-starred with Marsha Mason in the military drama Heartbreak Ridge, about the 1983 United States invasion of Grenada. He portrays an United States Marine Gunnery Sergeant veteran of the Korean War and Vietnam War who realizes he is nearing the end of his military service. Production and filming were marred by internal disagreements between Eastwood and long-time friend and producer Fritz Manes, as well as between Eastwood and the United States Department of Defense who expressed contempt for the film.^[173][174] At the time, the film was a commercial rather than a critical success, and has only come to be viewed more favorably in recent times.^[175] The film grossed $70 million domestically.^[176]
Eastwood starred in The Dead Pool (1988), the fifth and final film in the Dirty Harry series. It co-starred Patricia Clarkson, Liam Neeson, and a young Jim Carrey who plays Johnny Squares, a drug-addled rock star and the first of the victims on a list of celebrities drawn up by horror film director Peter Swan (Neeson) who are deemed most likely to die, the so-called "Dead Pool". The list is stolen by an obsessed fan who, in mimicking his favorite director, makes his way through the list killing off celebrities, of which Dirty Harry is also included. The Dead Pool grossed nearly $38 million, relatively low receipts for a Dirty Harry film. It is generally viewed as the weakest film of the series, though Roger Ebert thought it was as good as the original.^[177][178]
Eastwood began working on smaller, more personal projects and experienced a lull in his career between 1988 and 1992. Always interested in jazz, he directed Bird (1988), a biopic starring Forest Whitaker as jazz musician Charlie "Bird" Parker. Alto saxophonist Jackie McLean and Spike Lee, son of jazz bassist Bill Lee and a long time critic of Eastwood, criticized the characterization of Charlie Parker remarking that it did not capture his true essence and sense of humor.^[179] Eastwood received two Golden Globes for the film, the Cecil B. DeMille Award for his lifelong contribution, and the Best Director award. However, Bird was a commercial failure, earning just $11 million, which Eastwood attributed to the declining interest in jazz among black people.^[180] Carrey would appear with Eastwood again in the poorly received comedy Pink Cadillac (1989). The film is about a bounty hunter and a group of white supremacists chasing an innocent woman (Bernadette Peters) who tries to outrun everyone in her husband's prized pink Cadillac. The film failed both critically and commercially,^[181] earning barely more than Bird and marking a low point in Eastwood's career.^[182]

1990s