Today’s topic is the body of work I’d like to call: “Clint Eastwood’s second act.” The films that came after the roles we grew up with—the TV show cowboy, the Spaghetti Western star, the Dirty Harry years. But calling the films that Eastwood has made in this century his “second act” may be inaccurate. It’s probably best to call them the product of his fifth or sixth act. And who knows how many more he has in him. He’s 87 right now and the 39th film he directed (15:17 to Paris) came out just last month.
Eastwood is probably the most protean and versatile figure in American film. In addition to the 39 films he’s directed, he has 70 credits as an actor and 44 as a producer. He has also composed 8 full film scores, and put together the soundtrack on another 30 films. Did you know he is a noted jazz pianist and composer? Oh, and then there was that part where he was mayor of Carmel-By-the Sea, a tiny enclave on the coast, a couple of hours south of San Francisco.
As the new millenium dawned in 2000, Eastwood turned 70 and entered into a highly productive period in his life. Since 2000, Eastwood has directed a remarkable 15 films. Several of these are outstanding: Mystic River (2003), Million Dollar Baby (2004), Gran Torino (2008), and American Sniper (2014).
The masterwork in this batch is, of course, Million Dollar Baby. Based on a series of short stories by former boxing trainer Jerry Boyd (writing under the pen name of F.X. O’Toole), the film tells the story of the unique bond that develops between a crusty old boxing trainer (Eastwood) and an earnest but scrawny young woman from small town Missouri (Hilary Swank) whom he develops into a champion boxer.
The film was nominated for seven Academy Awards, and won four of them (Best Picture, Best Director, Best Actress, and Best Supporting Actor). Million Dollar Baby was Eastwood’s second Best Director Oscar (the first was 1992’s Unforgiven). The screenplay for Million Dollar Baby was written by Paul Haggis, who won a Best Picture of his own the following year for Crash.
If you’ve ever thought of renting Million Dollar Baby, but were put off by the idea that it’s an incredibly bleak tale, well, you’re right. It is an incredibly bleak tale. But it’s also mainly a story about determination and love. It’s an incredibly moving film. You may not go into a Clint Eastwood movie expecting to cry, but get ready. You’re gonna be bawlin’.
I’m not going to give any spoilers here; suffice it to say be sure to have a box of Kleenex and a couple of towels ready and available for the final act of the movie. And as you are sitting there weeping uncontrollably, just say to yourself: “The ladies love a man who can cry. The ladies love a man who can cry.” Which is not to say that this is a sentimental movie. Far from it. This is a gritty, hard-nosed movie about gritty, hard-nosed people. Hilary Swank is just breathtakingly good as the earnest small-town girl who fights to earn the respect of a cranky old pair of trainers. Oh, did I mention that Morgan Freeman is in this movie and won an Academy Award for Best Supporting Actor? And Eastwood himself turns in a wonderful performance in the lead as trainer Frankie Dunn.
A remarkable two-film set, both of these were directed by Eastwood. These two films tell the story of the Battle of Iwo Jima, one of the biggest battles ever fought in the history of warfare (with great heroism on both sides). The U.S. had 110,000 soldiers from all branches of the service and more than 500 battleships, vastly outnumbering a highly-entrenched Japanese military, which was dug into the small island of Iwo Jima in 1944. Flags of Our Fathers is the American side of the story, Letters from Iwo Jima the Japanese side. These are war movies on an epic scale. Both movies are definitely worth watching, but I would advise you watch them on consecutive days; bingeing them all at once might be too much.
Honestly, this is one of my favorite Clint Eastwood movies ever. Here he directs himself in the role of widowed and cranky Korean War veteran Walt Kowalski who surprisingly befriends an immigrant Hmong family next door, and ends up protecting their son from a Hmong gang trying to force the boy to join. It’s a fantastic movie, and inspiring too.
Clint Eastwood directs a musical! Well, sort of. This is called a “jukebox” musical. Which means none of the music is original but uses existing songs to form the score. In this case, the music is from Frankie Valli and the Four Seasons, and is based on a Broadway musical of the same name. Is it a great movie? No, but it’s got a lot of great songs and it’s an interesting look behind the scenes of one of the best singing groups of all time. Definitely worth queueing!
Chris Kyle (a real person) is basically just like Clint Eastwood from his movies Pale Rider (1985) or High Plains Drifter (1973): laconic, loyal, protective, and lethal. Kyle was the most prolific sniper in U.S. military history, with dozens and dozens of kills. He cannot stop returning to war even though it is eating his soul. Brilliant performance by Bradley Cooper in the lead. And the final battle sequence—a rooftop gun battle as a sand storm swirls in on Baghdad—is one of finest battle sequences ever put on film.
I’d also like to encourage you to catch a few of Eastwood's earlier masterpieces. After you finish this batch of films, it might be time to rewatch (or watch for the first time) movies like The Good, The Bad and the Ugly (1966), Dirty Harry (1971), the outstanding thriller Play Misty for Me (1971), or Pale Rider (1985.)
David Raether is a veteran TV writer and essayist. He worked for 12 years as a television sitcom writer/producer, including a 111-episode run on the ground-breaking ABC comedy “Roseanne.” His essays have been published by Salon.com, The Times of London, and Longforms.org, and have been lauded by The Atlantic Magazine and the BBC World Service. His memoir, Homeless: A Picaresque Memoir from Our Times, is awaiting publication.