The occasional somber acoustic guitar; direct, concise storytelling; an old man who argues with at least one other person in every other scene; a strong sense of good and bad; a blunt portrayal of violence—all of these are hallmarks ofClint Eastwood’s directorial filmography. His new movie,Juror #2, has received warm reviewsand apparently marks the end of acareer that has spanned over five decades. His best decade, however, is arguably the 2000s—landing him three Best Picture nominations and three Best Director nominations from the Academy.
Eastwood’s directorial debut was in 1971, and his fourth decade demonstrates how much he had learned about the craft by then. Though he wasn’t playing a literal cowboy anymore, Eastwood nevertheless brought his roots to the films he made in this new century. Some are more original, plausible, and worth rewatching than others, but a few of Eastwood’s most highly acclaimed and famous movies came out of the aughts. All of them are found below, ranked from worst to best.The weaker films aren’t disasters by any means, but the more successful ones carry lots of emotional power, boast high levels of drama or suspense, have the better screenplays, and largely still hold up today.
9’Blood Work'
Year of Release: 2002
In 2002’sBlood Work, Eastwood plays a renowned FBI investigator who starts a chase he has no business starting at his age. Two years later, McCaleb has a heart transplant. His new heart belonged to Gloria Torres, and her sister (Wanda de Jesús) wants him to help with Gloria’s case. He owes her that, even though he’s retired and doesn’t have a PI license. Armed with a box of donuts, he convinces two cops to let him take a look at the case.
Based on the Michael Connelly novel,Blood Workplays as a pretty traditional mystery. People repeatedly tell McCaleb that he looks like crap, there’s a false lead, the cops are yelling at each other, etc.Anjelica Hustonplays his frustrated doctor andJeff Danielsplays his neighbor and nonchalant partner. There’s a tacked-on romance, McCaleb pushes his new heart unrealistically far, and the cops should really be involved in the climax. Overall, it’s decent for those who like the genre.
Blood Work
Blood Work follows retired FBI profiler Terry McCaleb, who is recovering from a heart transplant and drawn back into investigation when his donor’s murder remains unsolved. As McCaleb pursues the case with determination, he unravels a complex web of connections, all while balancing the constraints of his fragile health.
Rent on Apple TV
8’Space Cowboys'
Year of Release: 2000
Clint Eastwood started the 2000s withSpace Cowboys, in which he plays Frank Corvin. Frank designed a satellite that’s going to crash and that only he can fix. Unfortunately, it’s too big to retrieve, and no one wants it destroyed. So NASA asks him for help, at which point Frank insists that they send his old team into space to fix it. Played by Eastwood,Tommy Lee Jones,Donald Sutherland, andJames Garner, Team Daedelus flies again.
It’s basicallyThe Right Stuff(one ofthe best movies nominated for Best Picture in the 80s) with old men who would never be allowed into space in real life. Funny moments include Jerry (Sutherland) not covering up for a physical and watching these guys warming up for a run. This movie has a very traditional structure and goes on a bit long, but Eastwood’s direction and the performances from these Hollywood legends help it basically succeed at giving the audience an entertaining (if implausible) ride.
7’Gran Torino'
Year of Release: 2008
Gran Torinois the most cowboy that Eastwood gets in the aughts. He plays a crotchety, recently widowed bigot named Walt who literally says “Get off my lawn!” with the intensity of a Korean War veteran you don’t want to screw with. He pulls out a gun on people more than once, and the viewer can see Eastwood’s history of gun-slinging Westerns at play. After helping his next door neighbor out of a scary situation, Walt gradually befriends him and his sister.
Despite Eastwood’s strong direction, some elements haven’t aged so well: the white-savior narrative, the offensive old man having exceptionally patient young neighbors, that barbershop scene, etc.The depiction of Hmong culture has also been criticizedfor its inaccuracies, stereotypes, and superficial exploration of their history. Moments like Walt running out of beer or the woman next door out-spitting him are still funny, and Daisy is a very welcome presence, but this is a flawed workthat should be considered a product of its time.
Gran Torino
Gran Torino follows a gruff, retired auto worker, Walt Kowalski, who sets out to confront his neighborhood’s changing cultural landscape. As he develops an unexpected friendship with a young Hmong teenager, Walt becomes involved in a struggle against local gang violence, leading to personal growth and unexpected solidarity.
6’Changeling'
Based on a true story,Changelingbegins in 1928 Los Angeles. Mrs. Collins (Angelina Jolie) left her son at home while she went to work, and returned to find he wasn’t there. The police tell her to wait until she calls for help, and the case winds up sending a ripple throughout the community. When the cops claim to have found her son, it’s clear to her and everyone who knew her son that this new kid is clearly an impostor.
One ofthe best movies about gaslighting,Changelingisn’t really about the mystery of whether this kid is her son; it’s more about widespread corruption and institutionalized sexism at its most extreme and cruel. This movie is definitely longer than it needs to be, and sometimes it feels like it wants to be ambiguous about what really happened to her son (which doesn’t really work). Despite all that,Angelina Joliewas rightfully nominated by the Academy for her stellar performance.
Changeling
Changeling is a 2008 American mystery crime drama film directed by Clint Eastwood and starring Angelina Jolie. The film is based on the true story of Christine Collins, a woman in 1928 Los Angeles whose son goes missing. When the police return a different boy to her, Collins confronts a corrupt and incompetent police department that insists the boy is her son. As she fights to uncover the truth, she exposes a conspiracy and battles against powerful forces. The film explores themes of loss, hope, and the quest for justice. Jolie’s performance, combined with Eastwood’s direction, received critical acclaim.
Rent on Amazon
5’Flags of Our Fathers'
Year of Release: 2006
The first ofEastwood’s sister films about the brutal Iwo Jima battle,Flags of Our Fathersis a moving work about three soldiers who tour the United States to raise war bonds in WWII. As they’ve just gone through a very traumatic battle, this job isn’t as easy as it sounds. The soldiers climbing a paper mache mountain to put up another flag is interspersed with flashbacks from the battlefield—showing the dissonance between how war is portrayed (heroic) and how it feels (much more complex).
The structure of this film is over-complicated, jumping back and forth in time and employing too many narrators. But there is also much to love here. A man falling overboard and a cake with red syrup over it are just two great images in a movie that revolves around the illusions of a famous image: the Iwo Jima photo. The surviving men from the picture are pressured to raise $14 billion for the war effort. With Ira Hayes’s (Adam Beach) story acting as the heart of the narrative, this film critiques our country’s history of racism and neglect of its veterans.
Flags of Our Fathers
Flags of Our Fathers is a war film directed by Clint Eastwood, based on the book by James Bradley and Ron Powers. The movie recounts the Battle of Iwo Jima, focusing on the iconic photograph of the flag raising and the soldiers involved. Through a series of flashbacks, it delves into the personal and collective experiences of the men who became symbolic heroes, examining both their wartime actions and post-war lives.
4’Mystic River'
Year of Release: 2003
One ofthe most thrilling Eastwood movies,Mystic Riverwas largely considered a grand return to form for the director.Sean Penngives us an Oscar winning performance as the man whose eldest daughter is found dead. In the aftermath, his heavily traumatized friend (Tim Robbinsin an Oscar-nominated performance) is considered a suspect while his other old friend (Kevin Bacon) conducts the formal police investigation.
Based on Dennis Lehane’s novel,Mystic Rivercasts the gritty streets of Boston in the dark shadows of tragedies both old and new. The atmosphere of mystery is strengthened by mysteries and regrets that can never be solved. For instance: How would Dave have turned out had he never gotten in that car? Not everything works, but the complexity of these characters and the intensity of Eastwood’s direction heightens this above the usual genre fare.
Mystic River
The tragic murder of a 19-year-old girl reunites three childhood friends still living in Boston–the victim’s gangster father, a detective, and the disturbed man they both suspect of killing her.
3’Invictus'
Year of Release: 2009
Named after the Victorian poem by William Ernest Henley,Invictusis one ofthe best sports movies of all time. This is largely because sports isn’t the point; instead, rugby is used as a way of bringing racial harmony to South Africa after it was recently under apartheid. Mandela (a stellarMorgan Freeman) has new white bodyguards who probably opposed the end of apartheid but have decided to stay. They disagree with his Black bodyguards about almost everything, even smiling.
The rugby team (called the Springboks) has been associated with apartheid for so long that only white people cheer for them. Led by their captain (Matt Damon), they go from being one of the worst teams in the league to competing for the 1995 Rugby World Cup. They also start to play with local children, leading to one of the movie’s most memorable sequences. The ending might have you thinking that racial tension has been resolved in South Africa (not so), but it’s still among Eastwood’s most affecting achievements.
Invictus, directed by Clint Eastwood, centers on the efforts of Nelson Mandela (played by Morgan Freeman) to unite a post-apartheid South Africa through the sport of rugby. The film follows Mandela’s collaboration with the national rugby team’s captain, Francois Pienaar (Matt Damon), to win the 1995 Rugby World Cup, symbolizing hope and reconciliation for the nation.
Watch on Max
2’Million Dollar Baby'
Year of Release: 2004
Having teamed up for Best Picture-winnerUnforgiven, Clint Eastwood and Morgan Freeman star together for the second time in Eastwood’s second Best Picture winner:Million Dollar Baby. Eastwood plays an overly cautious and sexist boxing manager, Frankie, whose mentee just left him to fight for the heavyweight title. Freeman (who won an Oscar for his role) plays his friend and former boxer, who helps run the gym. No Eastwood movie does old-men-bickering better than this.
No Eastwood movie is better with its use of acoustic guitar, either. Meanwhile,Hilary Swankwon an Oscar for her turn as Maggie, an inexperienced and aging yet fiercely determined fighter who convinces Frankie to train her. Maggie’s story is an emotional rollercoaster that’s difficult to forget. One ofthe best boxing moviesto date,Million Dollar Babyhas so many storytelling clichés that its immense emotional power is surprising. Despite the screenplay’s occasional melodrama, Eastwood’s direction is never more assured.
Million Dollar Baby
Frankie, an ill-tempered old coach, reluctantly agrees to train aspiring boxer Maggie. Impressed with her determination and talent, he helps her become the best, and the two soon form a close bond.
Watch on Netflix
1’Letters from Iwo Jima'
The second and more critically acclaimed of Eastwood’s Iwo Jima duo,Letters from Iwo Jimatells the story of that infamous battle from the Japanese perspective. The army is totally outnumbered, waiting for the Americans to arrive on the beaches of an island they will defend largely from Mount Suribachi.Ken Watanabedoes an excellent job as General Kuribayashi, whose brilliant tactics make sure his men won’t go down without a fight.
Yet many of them are told to kill themselves in the face of defeat, as per tradition.Kazunari Ninomiyaplays Private Saigo, whose wife and daughter are waiting for him back home. The sequence in which he watches other men blow themselves up with grenades is extremely intense, and potential viewers should keep in mind thatSaving Private Ryan’sSteven Spielbergco-produced this brutal examination of war. Spoken largely in Japanese,Letters From Iwo Jimaholds up today as possibly Eastwood’s best work of the 2000s.
Letters from Iwo Jima
The story of the battle of Iwo Jima between the United States and Imperial Japan during World War II, as told from the perspective of the Japanese who fought it.
