Film Lists

15:17 to Paris: Clint Eastwood’s Best Directorial Film from Each Full Decade

Clint Eastwood has been directing films – both good and bad – since 1971. Eastwood debuted in the director’s chair with Play Misty for Me, a thriller presenting Eastwood himself as a radio DJ, but one with the misfortune of acquainting a crazed, obsessed fan. Having cemented his cinematic status as both the Man with No Name (The Good, the Bad and the Ugly) and “Dirty” Harry Callahan (Dirty Harry), it would be expected that Eastwood would eventually direct westerns and a Dirty Harry instalment.

After having directed comedies and himself as a cop among other genres and roles in both the 1970s and 1980s, Eastwood, perhaps, legitimised himself as a big-time director with his Unforgiven Oscar success in 1993. Just over a decade later, Eastwood added two more Oscars to his collection with 2004’s Million Dollar Baby – it is reasonable to regard the latter as Eastwood’s last great directorial hit.

For the last decade or so, majority of Eastwood’s directorial work has presented real life figures and events:

  • Nelson Mandela (Morgan Freeman), Francois Pienaar (Matt Damon) and the 1995 Rugby World Cup – Invictus (2009).
  • FBI director J. Edgar Hoover (Leonardo DiCaprio) – Edgar (2011)
  • The Four Seasons (John Lloyd Young as Frankie Valli, Erich Bergen as Bob Gaudio, Michael Lomenda as Nick Massi, and Vincent Piazza as Tommy DeVito) – Jersey Boys (2014)
  • US Navy SEAL veteran Chris Kyle (Bradley Cooper) – American Sniper (2014)
  • Chesley “Sully” Sullenberger (Tom Hanks) and the “Miracle on the Hudson” – Sully (2016)
  • Spencer Stone, Anthony Sadler and Alek Skarlatos as themselves, and the 2015 Thalys train attack – 15:17 to Paris (2018)

Below is a list of Eastwood’s finest work as a director from each full decade.

The Outlaw Josey Wales (1976)

John Vernon as Fletcher: “Don’t piss down my back and tell me it’s raining!”

In the same vein as the Man with No Name, but with more heart and a human touch, Clint Eastwood’s Josey Wales is the most wanted man alive, but he’s on a journey of revenge.

The Outlaw Josey Wales opens with Wales’ house burned to the ground and family murdered in front of him – some of the imagery after the fact is truly haunting. On a brighter note, Eastwood’s panoramic imagery, learned from Sergio Leone, is truly astonishing and breathtaking – the shots are beautiful to the point where they can only look good on film cell, and not digital filmmaking.

After the murder of Josey Wales’ family, he then joins a band of Confederate guerrilla, though after defeat, Wales becomes, as mentioned above, the most wanted man alive…or within The Outlaw Josey Wales at least. The price on Josey Wales’ head is $5,000 – he has after him, the U.S. Cavalry, led by an organiser of his family’s murder, Terrill (Bill McKinney), who view Wales as Confederate scum, whilst bounty hunters too join the hunt, as Wales’ name transcends into infamy. Wales, though desired to be lonesome, soon attracts the company of two Native Americans (Lone Watie and Little Moonlight, played by Chief Dan George and Geraldine Keams respectively) as well as mother and granddaughter pair, Grandma Sarah and Laura Lee, played by Paula Trueman and Sondra Locke respectively. Inevitably, Josey Wales’ enemies catch up with him and his crew, but not every oppositional character faces revenge dished out by the outlaw…

With regards to feel and tone, The Outlaw Josey Wales is tremendous in creating tension and shock, though the element of surprise or not knowing what to expect within the next story event is a result of an almost road movie feel to this classic western.

Positives aside, the brief romance between Wales and Laura Lee (Sondra Locke), though expected, is almost unbearable to watch because Locke, at the time, looks so young, like, almost teenage young, despite being over 30. Thankfully, the brief romance isn’t at all explicit.

Sudden Impact (1983)

Clint Eastwood’s only directorial effort of a Dirty Harry film, Sudden Impact, is easily the best and most sophisticated after the original 1971 film. Sudden Impact presents Eastwood’s real life wife and frequent co-star, Sondra Locke, as Jennifer Spencer, a rape victim on a mission of revenge.

Opening with a cool soundtrack, Sudden Impact first presents Inspector Callahan as an outdated loser – he watches in court, a number of young crooks get away with a crime, due to the negligence of his police work. Later, however, Callahan redeems himself with the now iconic, “Go ahead, make my day.”

For what is a seriously dark Dirty Harry film, Sudden Impact’s first presentations of Callahan are light, comedic or embarrassing for the character. First losing to a bunch of kids in court was downright embarrassing for Callahan, and then prior to the “Go ahead, make my day.” in the diner, Callahan introduces himself to the armed robbers with a recollection of his usual black, non-sugared coffee, of which is slightly comedic and light. Later, after a body is found, Callahan, to a fellow officer, reveals that nothing annoys him more than a person who puts ketchup on a hotdog, as said fellow officer stuffs his face with a hot dog – “Nobody puts ketchup on a hot dog!”

Jennifer Spencer is a murder – she sets out to murder each rapist from within the gang of whom raped her and her sister. Sudden Impact is edgy in that how can Jennifer – Sudden Impact’s main murderer – be the villain of the film, when she is exacting her version of justice, whilst her rapists are able to roam free? Sudden Impact subsequently provokes its viewers to question whether what Jennifer did was right or not, and how far they would go for justice.    

Unforgiven (1992)

Did you honestly think that it was going to be anything else?

Clint Eastwood not only established himself as a big-time director with his return to beloved western genre in 1992’s Unforgiven, but he also gave the western genre its last great hit after a number of years hiding in the shadows of action and special effects blockbusters.

Like many good westerns, Unforgiven opens with horror: a prostitute is, undeservingly, facially disfigured after a vicious assault made by a cowboy. The cowboy in question was far from in receipt of a deserved punishment, therefore, other prostitutes from the same whorehouse demand justice and revenge…the hard way – they boast a reward for the deaths of both the guilty cowboy and his partner. Widower, former outlaw and failing farmer, Bill Munny (Eastwood), catches wind of this opportunity, thus he drafts in his former outlaw partner, Ned Logan (Morgan Freeman), to get the job done.

Opposing Bill Munny is the corrupt enforcement of the law: Little Bill Daggett (Gene Hackman), the sheriff.  Little Bill will do anything to eradicate any potential trouble from the town, Big Whiskey, of which he feels that he owns, though morals are not taken into consideration – for example, English Bob (Richard Harris), a veteran gunfighter, enters town in regards the reward for the prostitute-endorsed cowboy murder, and instead of politely sending Bob back on his way, Little Bill has Bob beaten to a pulp to send a message and warning to others with the intention of bringing murder into the town of Big Whiskey.

Bill Munny’s journey from weak and depressed farmer to skilled re-invented gunslinger in Unforgiven is truly remarkable. Munny’s journey from bottom to top, for one last time, is almost reminiscent of what Unforgiven does to the western genre. Truthfully, in 1992, the western was decades past its prime and was more or less dead in a serious manner, like Munny at the beginning of Unforgiven. Munny’s transformation back into a skilled gunslinger, back to his best for a very long time, is then replicated in the instance of Unforgiven – regarded as a revisionist western – bringing a new lease of life to the western genre, even just for one outing.

Million Dollar Baby (2004)

In the 1970s it was Rocky. In the 1980s it was Raging Bull. In the 1990s it was The Hurricane. Then in the 2000s it was Clint Eastwood’s Million Dollar Baby.

The sports drama is a rare one for Eastwood, but one that handed him his third and fourth Oscars. As mentioned in this article’s introduction, Million Dollar Baby is reasonable to be regarded as Eastwood’s last great directorial hit.

Starring a post-The Core Hilary Swank, with support given by Unforgiven co-stars, Eastwood and Morgan Freeman, Million Dollar Baby presents Maggie Fitzgerald’s (Hilary Swank) almost rags-to-riches story from working in a diner, bringing home leftovers in foil, to competing as a professional boxer.

The trainer, Frankie Dunn (Eastwood), obviously has some prehistoric views or opinions – such as training a female boxer, but an outdated viewpoint is a conventional trope of an Eastwood character – previous and future examples: Inspector Callahan was overly reluctant to work with a female police officer in 1976’s The Enforcer, and later in 2008’s Gran Torino, Walt Kowalski is initially racist and prejudice towards his neighbours, though he does later transition to good.

Despite the sport of boxing hosting an amount of relevancy, Million Dollar Baby’s main purpose is, essentially, everything surrounding boxing – the desire, the training, the background. Unlike some of the Rocky sequels, Million Dollar Baby’s emotion is sold not on a fighter’s victory, but their cost of doing what they aspire to. Million Dollar Baby is utterly heartbreaking.

Honourable Mention: 1990s – The Bridges of Madison County (1995)

After Steven Spielberg eventually turned his back on directing the film adaptation of Robert James Waller’s 1992 novel, The Bridges of Madison County, the directorial role then landed with Clint Eastwood, of which created the challenge of adapting a romance novel into a respectable romantic film. One would have to ask: which is the harder of two challenges – Eastwood directing a romantic film or Eastwood starring in a romantic film?

The romance in The Bridges of Madison County is between Francesca Johnson (Streep), a farmer’s wife, and Robert Kincaid (Eastwood), a lonesome photographer, in 1965. A romance between Meryl Streep and Clint Eastwood – okay!

The Bridges of Madison County opens with Michael and Carolyn Johnson, the children of Francesca, are discovering the contents of their deceased mother’s safety deposit box and will. Further on, diaries are discovered, of which read of a brief romance between their mother and a National Geographic photographer. As the siblings read the diaries, the plot then transcends to Francesca’s voice-over during the period of which the diary entries were written. After asking for directions, it is rather remarkable how there’s an overwhelming bond between Francesca and Robert, thus she subsequently invites he over for dinner, and from there on, an extramarital romance is inevitable.

It is somewhat refreshing to see a 60-something Eastwood engage in a romance, rather than present the conventional confident, but tough stance, and catchy one-liners.

Morally, The Bridges of Madison County is an awkward one to consider. Whilst beautiful throughout and even heartbreaking at times, Francesca is a married woman with two children, who enjoys a short-lived affair whilst the family is away. However, it is respectable that Francesca placed her family first and chose not to run away with Robert, though their concluding scene together is so damningly painful. 

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