Clint Eastwood: 10 essential films as director

From The Outlaw Josey Wales to Unforgiven, we revisit some of the highest peaks from one of the finest bodies of work in American film.

Craig Williams
Updated:

Sully (2016)

Sully (2016)

“I wanted to play it with an economy of words and create this whole feeling through attitude and movement.” This is how Clint Eastwood described his role as the Man with No Name in Sergio Leone’s Dollars trilogy, but it’s equally appropriate as a summation of his directorial style. Over the course of almost five decades, beginning with Play Misty for Me in 1971, Eastwood has created one of the best bodies of work in American cinema. Known for his classical, muscular style, he has the work ethic of a studio craftsman and, though his work covers a diverse range of subjects and genres, his primary interest is in the shades of grey that underlie so many of the American myths.

The Outlaw Josey Wales (1976)

The Outlaw Josey Wales (1976)

The New Hollywood movement was the year zero of the modern western, with films such as Sam Peckinpah’s The Wild Bunch (1969) and Robert Altman’s McCabe & Mrs. Miller (1971) drawing on contemporary anxieties – from Watergate to Vietnam – to redefine the genre for an increasingly pessimistic audience living through turbulent times. The Outlaw Josey Wales was the best of the crop. A bold, violent story of a Missouri farmer on the run from the soldiers who killed his family, it was the defining western of the decade – a feat Eastwood would go on to repeat in the 1980s with Pale Rider (1985) and in the 1990s with Unforgiven (1992).

Bronco Billy (1980)

Bronco Billy (1980)

Eastwood has always been aware of his own myth, and while this self-reflexive streak has been especially apparent in his recent work – Rawhide appearing on the television in Jersey Boys (2014) is a particular highlight – the most notable example is 1980’s Bronco Billy. In perhaps Eastwood’s most underrated film, he stars as Bronco Billy McCoy, the “fastest gun in the west” and star of a ragtag travelling revue show. It’s a loose, open-hearted film, which not only subverts the mythology of western movies but that of Eastwood himself as an actor and director. “If, as a film director, I ever wanted to say something, you’ll find it in Bronco Billy,” he said at the time.

Honkytonk Man (1982)

Honkytonk Man (1982)

From The Gauntlet (1977) to Space Cowboys (2000), many of Eastwood’s pictures appropriate elements of the western into different settings. In Honkytonk Man, a terrific Depression-set musical drama, the outlaws are country singer Red (Eastwood) and his nephew Whit (Clint’s son, Kyle) and the frontier is Nashville’s Grand Ole Opry. The bond between surrogate fathers and sons is a recurring theme in the Eastwood canon, with the former typically prompting the redemption of the latter. It’s in the relationship between the convict and young boy in A Perfect World (1993) and between the Korean war veteran and his neighbour in Gran Torino (2008).

Bird (1988)

Bird (1988)

“I’ve always felt that jazz and blues were true American art forms. Maybe the only really original art forms that we have.” This is how Eastwood described his first love in Piano Blues (2003), the exceptional documentary he made for Martin Scorsese’s The Blues series. An accomplished musician in his own right – he composed the scores to many of his own films – jazz is Eastwood’s great passion and, thus, Bird, his biopic of saxophone colossus Charlie Parker, finds the director at his most reverent. Eschewing the classic biopic pitfalls, it’s a mournful, downbeat picture, with Eastwood constructing a patchwork portrait of a troubled genius through the miscellanea of his life. He would later adopt a similar approach in the hugely underrated J. Edgar (2011).

Unforgiven (1992)

Unforgiven (1992)

Unforgiven is widely (and justly) acknowledged as Eastwood’s greatest achievement. Just as John Ford’s The Man Who Shot Liberty Valance (1962) served as the epitaph for the classical Hollywood western, Unforgiven marked the end of the New Hollywood western aesthetic – a sensibility defined by hard-worn pessimism and a revisionist approach to frontier mythology. The film was dedicated to Eastwood’s mentor Sergio Leone, and it took stock of the way the genre had changed since the pair’s celebrated Dollars trilogy in the 1960s. He would go on to make a similar tribute to Don Siegel in 2008 with Gran Torino, a touching but muscular picture that eulogised his avenger persona.

The Bridges of Madison County (1995)

The Bridges of Madison County (1995)

The melodrama is a perfect form for Eastwood the classicist and master storyteller, and The Bridges of Madison County is one of his best films. A beautiful, melancholic tearjerker, it stars Meryl Streep as a lonely housewife who falls in love with a photographer (Eastwood) while her family are away on a trip. The portrayal of women has never been Eastwood’s strong suit, with depictions ranging from the hysterical (Play Misty for Me) to the downright hateful (1975’s The Eiger Sanction), but Streep’s Francesca marked a turning point in this respect, laying the groundwork for the powerful brand of female resilience that would define later films like Million Dollar Baby (2004) and Changeling (2008).

Blood Work (2002)

Blood Work (2002)

The transition between Midnight in the Garden of Good and Evil (1997), which signaled the end of Eastwood’s 1990s purple patch, and Mystic River (2003), the film that began his late-master period, was marked by three low-key crime procedurals: Absolute Power (1997), True Crime (1999) and Blood Work. The latter was the first of Eastwood’s films shot by Tom Stern, the cinematographer who would create the unique visual palate of the director’s work in the new century. From the photographic negative effect in a key sequence to the signature Eastwood shot of the face of an avenger emerging from the shadows (an idea that’s brilliantly subverted in the opening shot of his latest film, Sully), his induction into Clint’s milieu was particularly striking.

Million Dollar Baby (2004)

Million Dollar Baby (2004)

Eastwood’s political views have often been used by as a lens through which to view his films, but the best of his work often represents a reconciliation between his personal conservatism and his auteurist concerns, with the emphasis always on what is right for the story he’s telling. This accounts for the uncharacteristically liberal streak in some of his later films, such as Changeling and J. Edgar, but it reached its apex with the powerful third act of Million Dollar Baby, Eastwood’s moving boxing drama in which he stars as an over-the-hill trainer who coaches an ambitious young boxer played by Hilary Swank.

Flags of Our Fathers / Letters from Iwo Jima (2006)

Letters from Iwo Jima (2006)

All of Eastwood’s post-Mystic River films are rich with the notion that there’s always another perspective running concurrent with the main narrative. It’s in the presence of the Iraqi shooter in American Sniper (2014) and in the brilliant use of to-camera monologues in Jersey Boys. In 2006, Eastwood made a pair of Second World War-set features built on this very idea. Flags of Our Fathers is the loose, rambling American war movie – in the same vein perhaps as Sam Fuller’s The Big Red One (1980) – whereas Letters from Iwo Jima is the more sombre, fatalistic Japanese flipside. Taken together, they are the best war movies of the 2000s.

American Sniper (2014)

American Sniper (2014)

From Heartbreak Ridge (1986) to Invictus (2009), the complex negotiation of heroism is an idea that runs throughout Eastwood’s work, but the recent one-two punch of American Sniper and Sully put forward a more precarious vision of heroism under attack, expertly charting the gulf between the men and the legends that precede them. The former, a knotty, morally ambivalent picture about Chris Kyle (Bradley Cooper), the Navy SEAL who was the most lethal sniper in US military history, demonstrates Eastwood’s innate understanding of the mythology underpinning the notion of American heroism and, more importantly, the effect it had on the men struggling to live up to that ideal.

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