Westerns have maintained their place of pride on the coveted Hollywood mantelpiece for a little over a century. Yet, you’d have to stretch back as far as 1899 to source the first Western ever to be captured on film. Titled Kidnapping By Indians, the movie wasn’t shot in the desolate, often sun-drenched surroundings of New Mexico, Arizona, Nevada, or even in a Hollywood studio, but Blackburn, England. Ironically, one of the wettest, grayest and greenest places in the UK, far removed from the deserts and mountain plains of Sierra Nevada. Cowboys, Indians, saloon shootouts, and tumbleweed are all associated with the Western genre, but there isn’t anything or anyone that encompasses yee-haw! flicks more than the legendary, eye-squinting, Clint Eastwood.
The actor-turned-director made his name in the television series Rawhide, before reaching the lofty heights of international stardom, appearing in Spaghetti Western films such as The Good, The Bad, and The Ugly, A Fistful of Dollars, and For a Few Dollars More. While much of his early success came riding horseback, hunting down the outlaws of the American Frontier, and frequenting the saloons of Santa Cruz and El Paso, Eastwood has acted and directed in countless movies that are by far and large a departure from the Wild West. The major change happened after Unforgiven in 1992, when Eastwood began to almost entirely stop making Westerns (until, arguably, Cry Macho in 2021). Let’s take a look at these last 30 years of his directing career, and the best Clint Eastwood movies to have come from them.
7. A Perfect World
Kevin Costner stars as Robert “Butch” Haynes, in the Clint Eastwood movie A Perfect World. The film follows Haynes, a prison escapee who kidnaps orphan Phillip (T.J. Lowther) and goes on the run, with the ranger, Chief Red Garnett (Eastwood), in hot pursuit. The pair forms an unlikely bond during their encounter, and a father-son-like relationship ensues. A Perfect World makes for gratifying and charming viewing, as the protagonists provide one another with sanctuary from the stresses, reality, and hardships of everyday life.
6. The Bridges of Madison County
Based on Robert James Waller’s 1992 novella of the same name, The Bridges of Madison County jumps between the present and 1965, documenting the love affair between Francesca (Meryl Streep) and Robert (Clint Eastwood). Whilst her husband and children are away, Francesca experiences a chance encounter with a National Geographic photographer, Robert Kincaid. During the four days the couple spends together, they share an intense and passionate love that ultimately remains undeveloped.
Running concurrently with the happenings in 1965 is the present-day, where recently deceased Francesca has left a safe deposit box containing the remnants of that fateful four days she spent with Robert. Francesca’s children are left to piece together their mother’s surreptitious affair 30-years prior. Even in a progressive, 21st-century society, extramarital activities are seldom approved of, yet The Bridges of Madison County seemingly dismantles the social construct of marriage and lays bare the vulnerabilities, complexities, and failings of the human character, in turn, positioning the audience in a place of understanding, acceptance, and forgiveness.
5. Changeling
The definition of a Changeling is one of mystical nature: a deformed fairy spawn that is subsequently exchanged for a human child; this captures the very essence of the 2008 Clint Eastwood movie starring Angelina Jolie as Christine Collins. Clint Eastwood appears to enjoy creating motion pictures where the core nucleus focuses on real-life events, from Sully to Richard Jewell, to American Sniper and several more in-between.
Changeling is also inspired by true events. It details the story of Christine Collins, a single mother in 1920s Los Angeles whose son (Walter) is kidnaped and “found” by the LAPD. It transpires that the boy “found” and returned to her care, is an intruder, and not her missing son. Despite the boy’s best efforts at proving otherwise, Christine remains adamant that he is not her son, pointing at several physical discrepancies.
The film explores the increasingly disturbing truth, as it takes twist after turn before culminating in an alarming, rather deranged manner. The movie delves deeply into themes of police mistrust, negligence, love, and loss, taking the audience on a journey through a mother’s heartache as she frantically attempts to locate her missing son with disastrous consequences.
4. Mystic River
An adaptation of Dennis Lehane’s novel, Mystic River includes a stellar ensemble cast, with the likes of Kevin Bacon, Sean Penn, Laurence Fishburn, Tim Robbins, and Laura Linney. Penn and Robbins claimed an Academy Award each for Best Actor and Best Supporting Actor, respectively. This mystery crime drama depicts the story of Jimmy, Dave, and Sean, who endeavor to solve the murder of Jimmy’s daughter, Katie. As Alan Morrison from Empire states, “While not quite the equal of the novel, it’s more complex, emotionally-charged and better acted than the average Hollywood thriller.”.
3. Letters from Iwo Jima
Letters from Iwo Jima is a touching, moving, and at times heartbreaking portrayal of the events that unfolded on the Japanese island of Iwo Jima during World War II. The islet played host to one of the bloodiest battles during the war between Japanese and American troops. The film was released just four months after its sister film, Eastwood’s Flags of Our Fathers, which depicted the same battle but from an American perspective.
With an American invasion imminent, outnumbered Japanese General Kuribayashi and his men attempt to hold off the US bombardment as American forces arrive at its shores. In the face of the inevitable, the movie pays tribute to the fearless and unwavering resolve of the Japanese soldiers, who were knowingly hoisted into a suicide mission. Letters from Iwo Jima confronts the devastation of war and the senseless, merciless act of mass slaughter, creating vast amounts of empathy by humanizing the ‘other’ side.
2. Gran Torino
Obstinate resistance to societal change + a reluctant act of kindness against one’s better judgment = eventual submission to the positive forces of change. Sounds like an equation to a Clint Eastwood movie; sounds like the formula to Gran Torino. In some cases, Clint Eastwood movies have possessed a certain air of predictability, which has undoubtedly affected the reception of some of his work. However, in the case of Gran Torino, the predictable element by no means hampers what is an otherwise brilliant film.
Following the story of disgruntled, racist war veteran Walt Kowalski, alienated by his experiences in Vietnam, the man detests his neighborhood which has lost its predominantly white middle-class identity to that of working-class Asian immigrants. Initially pig-headed, Walt develops a blossoming friendship with his Hmong neighbor, Thao, who works for him doing odd jobs around his house. The omnipresent danger of gang violence from local Hmong gangs leaves Thao and his family fearing for their safety, and Walt with a decision to make. As Roger Ebert put it, “Gran Torino is about two things, I believe. It’s about the belated flowering of a man’s better nature. And it’s about Americans of different races growing more open to one another in the new century.”
1. Million Dollar Baby
Million Dollar Baby took the 2005 Academy Awards by storm, laying claim to four Oscars, with two going to Clint Eastwood for Best Picture and Best Director. As far as awards go, this movie has been Eastwood’s most decorated as a director (at least since 1992). It depicts the story of aspiring boxer Maggie Fitzgerald (Hilary Swank), who has to persuade a doubtful and stubborn boxing trainer, Frankie Dunn, to take her on as a trainee.
Throughout the film’s 132-minute runtime, the political nature of boxing, as well as the constant struggle to be taken seriously as a female boxer is developed. Yet, Million Dollar Baby extends far beyond just being a film about boxing, and reaches into the realms of the characters’ self-discovery and wholehearted acceptance of who they are, recognizing the processes of fortune and misfortune and how these have shaped their lives for the better. It’s a stunningly emotional modern classic.