There is only one Clint Eastwood. In all likelihood, no one will ever replicate Eastwood’s success and output. How many creatives in the business can say they were once the top actor and director in all of Hollywood? Not many can hold a candle to Eastwood's accolades and box office receipts as a triple-threat filmmaker.
While Eastwood’s best days were before the turn of the century, the 94-year-old filmmaker managed to direct some seminal classics post-2000. Keep in mind: In 2000, Eastwood was 70 and had already directed nearly 20 movies. Eastwood’s proficiency in the third half of his career is truly admirable.
This year, Eastwood directed “Juror No. 2,” which is streaming now on Max. In honor of what might be his last movie, these are the rankings for Eastwood’s seven best-directed movies of the century.
7. ‘American Sniper’
![American Sniper - Official Trailer 2 [HD] - YouTube](https://img.youtube.com/vi/5bP1f_1o-zo/maxresdefault.jpg)
The first of two war films on this list is “American Sniper,” Eastwood’s biopic about Chris Kyle, one of the most decorated marksmen in U.S. history. Bradley Cooper plays Kyle, the patriotic Texan who enlists in the Navy and becomes a SEAL. After the 9/11 attacks, Kyle is deployed to Iraq, where he witnesses firsthand the horrors of war. As bad as it gets in the Middle East, nothing could have prepared Kyle for his biggest challenge: adjusting to life at home.
A beefed-up Cooper, who gained 40 pounds for the role, successfully showcases Kyle’s patriotism toward his country as well as his vulnerability as a father and husband. Fake baby controversy aside, Eastwood effectively captures an American hero in a constant battle with his morality.
►Rent/buy on Amazon or Apple
6. ‘The Mule’
Eastwood loves to explore mortality through problematic characters. In “The Mule,” Eastwood plays Earl Stone, a Korean War veteran in financial ruin with his business going bankrupt and his house on the verge of foreclosure. Desperate for money, Earl takes a job as a drug mule for the cartel. Earl’s old age and lack of a criminal record allow him to move drugs fairly easily and become one of the cartel’s top mules.
Earl’s prowess puts him on the radar of Special Agent Colin Bates (Bradley Cooper), who is close to bringing down the entire operation. Eastwood is the perfect actor to play the guilt-ridden man searching for forgiveness in the final stages of his life. “The Mule” is definitively Eastwood’s best acting performance of the last 15 years.
►Rent/buy on Amazon or Apple
5. ‘Million Dollar Baby’
Frankie Dunn (Eastwood) is an old curmudgeon and washed-up boxing trainer living in Los Angeles. Besides Eddie “Scrap Iron” Durpis (Morgan Freeman), Frankie avoids conversation with others at all costs. That is until amateur boxer Maggie Fitzgerald (Hilary Swank) convinces Frankie to be her trainer. Together, the duo form a familial bond, something Frankie has been missing for most of his life.
Admittedly, “Million Dollar Baby” isn’t a movie that comes up often when determining what to watch for the weekend. It’s bleak and depressing, so I can’t blame anyone who only streams it once and never returns. Nevertheless, Eastwood won his third and fourth Oscars for “Million Dollar Baby,” so it definitely deserves a watch.
►Stream it now on Netflix
4. ‘Gran Torino’
While “Gran Torino” has politically charged problems with representation and authenticity, it features one of Eastwood’s best-jaded characters in Walt Kowalski. The widow and Korean War veteran is the literal definition of a “get off my lawn” guy, as Walt holds prejudices against many of the minorities in his neighborhood.
After Walt catches Hmong teenager Thao (Bee Vang) trying to steal his prized car, the elder statesman agrees to let the boy work for him as penance. Over time, Walt develops a soft spot for Thao, as the two form an unlikely bond. Again, “Gran Torino” is not without its issues, but no one plays tough, masculine characters with deep-seated emotional issues better than Eastwood.
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3. ‘Juror No. 2’
Eastwood tackles the search for truth in a flawed justice system in “Juror No. 2.” Nicholas Hoult gives an inspired performance as Justin Kemp, a journalist summoned for jury duty on a murder trial. The twist: Justin may have been responsible for the victim’s death. “Juror No. 2” is Eastwood’s version of “12 Angry Men,” but with more self-guilt from a protagonist experiencing a crisis of conscience.
Warner Bros. did Eastwood dirty by burying “Juror No. 2.” This is a filmmaker who has been working with Warner Bros. since 1971. Yet the studio was reluctant to give “Juror No. 2,” which might be Eastwood’s final film before retirement, a theatrical release and awards season campaign. For decades of service, Eastwood’s drama played in less than 50 theaters before it went to streaming. Shame on them.
►Stream it now on Max
2. ‘Letters From Iwo Jima’
Throughout his career, Eastwood has always been pegged as an anti-war filmmaker. The Oscar winner loves examining morally confused soldiers who question their purpose in war. In 2006, Eastwood released two war movies about the Battle of Iwo Jima. “Flags of Our Fathers” is told from the American perspective, while the superior movie, “Letters from Iwo Jima,” portrays the battle from the Japanese's perspective.
General Tadamichi Kuribayashi (Ken Watanabe) knows Japan is losing the war and realizes most of his troops will die at Iwo Jima. Still, Kuribayashi does his best to keep his boys alive long enough to give themselves a fighting chance. Eastwood’s steady direction is extremely thoughtful in its depiction of the Japanese soldiers. In Eastwood’s mind, there are no winners in war; there are only survivors.
►Stream it now on Paramount Plus
1. ‘Mystic River’
In “Mystic River,” Eastwood shows how trauma in the past, if left unhandled, will affect the future. Based on Dennis Lehane’s crime novel of the same name, “Mystic River” follows the lives of childhood friends Jimmy Markum (Sean Penn), Sean Devine (Kevin Bacon), and Dave Boyle (Tim Robbins) in Boston. As kids, two men sexually abuse Dave, which becomes an inflection point in their lives.
25 years later, Jimmy is an ex-con, Sean is a cop, and Dave is a blue-collar worker still tormented over the abuse. After the death of Jimmy’s daughter, Sean leads the task force to find the culprit. When Dave becomes a suspect, Jimmy decides to bypass Sean and conduct his own investigation, taking the law into his own hands. All of Eastwood’s favorite themes — guilt, morality, vengeance, and justice — are explored in this spectacular crime drama that will floor you by the film’s climax.
►Rent/buy on Amazon or Apple
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