Clint Eastwood Through The Years: From Actor to Award-Winning Director

From almost quitting the entertainment industry to becoming an Academy Award-winning director and actor, Clint Eastwood has come a long way in his career.

Eastwood was drafted into the U.S. Army in 1950 and discharged in 1953. He was stationed at Fort Ord in California and almost lost his life when the Douglas AD Bomber plane ran out of fuel, crashing into the ocean. Escaping with a life raft, Eastwood and the pilot were able to swim two miles back to shore.

Universal Studios employee Chuck Hill had seen Eastwood while filming at Fort Ord and brought him to the company. Eastwood’s tall stature and good looks were impressive and he ended up signing a contract with Universal in 1954.

After working closely with directors such as Sergio Leone and Don Siegel, Eastwood decided to try getting behind the camera himself. Siegel gave him a thumbs up for his script and Eastwood made his directorial debut with the 1971 thriller Play Misty for Me. Throughout the next few decades, Eastwood continued to establish his career as a reputable actor and director.

Keep scrolling to see the award-winning actor and director’s life in photos. 

Eastwood jumped around agencies at the beginning of his career. He first signed with Universal in 1954 and the studio arranged for Eastwood to attend acting classes. 
Despite developing his talent, Eastwood’s contract with Universal was terminated the following year. Then he joined Marsh Agency where he landed a large role in The First Traveling Saleslady and later starred in Escapade in Japan. Still struggling to find his footing, Eastwood switched to Kumin-Olenick Agency in 1956, then Mitchell Gertz in 1957. He was able to land a handful of smaller roles through both agencies but was still waiting to have his big breakthrough. 
“After about the first five years or so, four years, I started really getting to the point where I started wondering,” he said in a revived interview with Paul Nelson. “You go through periods of really liking it and wanting to be involved – but struggling.” 
It was the 1958 western Ambush at Cimarron Pass, however, that made Eastwood almost quit the industry.
“That was almost the picture that made me decide to quit. At the time I was thinking ‘Maybe I should give up the business and go into something else’.” Eastwood told Brian Linehan in a 1974 interview. He continued to credit his then-wife, Margaret Johnson, for pushing him to keep going. “My wife – I’ll have to give her a lot of credit – she kinda talked me into hanging in there and about six months after that I got Rawhide.”  
Earl Leaf/Michael Ochs Archives/Getty Images
The Academy Award-winning director had his breakthrough role as Rowdy Yates in CBS’s western series Rawhide. The popular Western TV series kick-started Eastwood’s interest in directing. 
“I asked Eric Fleming, ‘Would you be adverse to my directing?’ He said, ‘Not at all, I’d be for it.’ So I went to the producer and he said great. Evidently, he didn’t say great behind my back; but he said great at the time,” Eastwood shared with Patrick McGilligam in the 1999 interview book Clint Eastwood: Interviews. “He said, ‘I’ll tell you what, why don’t you direct some trailers for us; coming attractions for next season’s shows?’ I said, ‘Terrific. I’ll do it for nothing and then I’ll do an episode.’ And I did the trailers.” 
Sunset Boulevard/Corbis via Getty Images
Opposite of his role in Rawhide, Eastwood became an antihero in the Dollars Trilogy directed by Sergio Leone. Filmed in the plains of Spain, Eastwood discussed production in a 1977 interview with Iain Johnstone. He was hesitant about the film at first but warmed up to it once shooting started.
“I liked it though and I felt that maybe a European approach would give the western a new flavor – because I thought it had been in a very stagnant period at that point,” Eastwood told Johnstone. The series hit the United States in 1967 and brought Eastwood a mass amount of fame as an actor. 
Silver Screen Collection/Getty Images
The Gran Torino actor met director Don Siegel and the pair formed a close friendship as well as partnership. Over a decade, the two collaborated on a total of five movies: Coogan’s Bluff (1968), Two Mules for Sister Sara (1970), The Beguiled (1971), Dirty Harry (1971), and Escape from Alcatraz (1979). 
In 2006, a year after winning the Directors Guild of America Lifetime Achievement Award, Eastwood was interviewed by the DGA quarterly and revealed Siegel’s support in his directorial debut. “When I decided I wanted to direct, I went to him and I said, ‘You know, I’ve got this little project.’ I even asked him to read it for me,” Eastwood said at the time. “He liked the script and said, ‘You should direct it. Let me be the first to sign your DGA application card.’ So I got into the Guild and I was off and running.”
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In 1971, the Dirty Harry star made his directorial debut with the psychological thriller film Play Misty for Me. His first western film, High Plains Drifter, was released two years later in 1973. With an established reputation as a film director, Eastwood continued to direct and star in commercially successful movies throughout the 70s and 80s including The Eiger Sanction (1975), The Outlaw Josey Wales (1976), and the fourth installation of the Dirty Harry series Sudden Impact (1983). 
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Eastwood won his first Academy Award in 1993 with Unforgiven. The film received titles of Best Picture and Best Director. 
In 1994, Eastwood received one of France’s highest honor awards, the Ordre des Arts et des Lettres, at the Cannes Film Festival. A year later, he was awarded the Irving G. Thalberg Memorial Award at the 67th Academy Awards for a lifetime achievement in film production.  
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The Beguiled actor took home the Life Achievement Award by the Screen Actors Guild in 2003. In the same year, Eastwood directed Mystic River, which debuted at the Cannes Film Festival and won the Golden Coach Award.  
Steve Grayson/WireImage
Eastwood directed and starred in the 2004 sports drama Million Dollar Baby following the sport of boxing. The film was a box office hit domestically and internationally. It garnered seven Academy Award nominations and four wins: Best Picture, Best Director, Best Actress, and Best Supporting Actor. Eastwood was 74 at the time and became the oldest of only eighteen directors to have directed two or more Best Picture winners.  
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After Million Dollar Baby, Eastwood continued to direct but did not appear in any films until Gran Torino in 2008. He released two films in 2006 about World War II’s Battle of Iwo Jima. The first, Flags of Our Fathers, featured the debut of Eastwood’s youngest son Scott. The second, Letters from Iwo, won a Golden Globe for Best Foreign Language Film.  
Eastwood starred alongside his son Scott in Gran Torino, while his oldest son, Kyle, assisted in composing the film’s score. It’s one of Eastwood’s highest-grossing films, earning almost $30 million in its opening weekend. Eastwood was awarded Best Actor for his performance by the National Board of Review. 
The Sully director adapted Chis Kyle’s 2012 autobiography, American Sniper, into the 2014 film of the same name. Another largely commercial success, it was nominated for an Academy Award and won the Japan Academy Prize for Foreign Film in 2016. 
TSM/Bauer-Griffin/GC Images
Eastwood has been married twice and has eight children. The Hollywood star married his first wife Margaret Johnson in 1953. Early on in their relationship, Eastwood had an affair which resulted in his first daughter, Laurie, born in 1959, whom he did not reconnect with until years later. 
From 1959 to 1973, Eastwood had a lengthy affair with stuntwoman Roxanne Tunis which produced his second daughter, Kimber, in 1964. Years after Kimber’s birth, Eastwood and Johnson would have two children, Kyle and Alison, born in 1968 and 1972, respectively.
Around the mid-70s, Eastwood began an affair with costar Sondra Locke, causing him and Johnson to call it quits in 1979. The two weren’t officially divorced until 1984. Locke and Eastwood continued their love affair, but he would also go on to have two children with Jacelyn Reeves, son Scott born in 1986, and daughter Kathryn born in 1988. Locke and Eastwood made headlines when they split a year after Kathryn’s birth, but by that time he had already met Frances Fisher. The two secretly began dating and share a daughter named Francesca, whom they welcome in 1993. Two years after Francesca’s birth, the pair fully separated in 1995. 
Right after Eastwood and Fisher split, he started dating news anchor Dina Ruiz and proposed in September 1995. The two were wed in March 1996 at Steve Wynn’s – a friend of Eastwood’s – estate. The married couple welcomed daughter Morgan in December that same year. 
In early 2013, Eastwood and Erica Tomlinson-Fisher, the ex-wife of one of Dina’s old friends, began dating. Dina filed for divorce and the two split in September of that year.  
Following Tomlinson-Fisher and Eastwood’s relationship, the film director met Christina Sandera and the two began dating in 2014. The pair made an appearance at the 2015 Oscars and have kept most of their relationship private. 
Kevin Winter/Getty Images
Eastwood starred in and directed The Mule, his first acting role since 2012’s Trouble with the Curve. The 2018 film based on a true story became Eastwood’s third highest-earning film in an opening weekend throughout his acting career. 
Expected to be Eastwood’s final film, Juror No. 2 is an American thriller and stars Nicholas Hoult and Toni Collette. Production started in June 2023 but was put on hold the following month due to the 2023 SAG-AFTRA strike. 
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