Trouble With The Clint: Should Eastwood Have Retired 20 Years Ago?

Clint Eastwood’s career, lately, has been a string of false endings. Every time the legendary actor-director turns up in a new role, it’s rumored to be his last. And without spoiling much, he gave himself two spectacular endings (one happy, one sad) in Million Dollar Baby and Gran Torino. Drop the curtain, turn off the lights, and call it a day, right?

Wrong. Eastwood’s back on screen this weekend in Trouble the Curve, a baseball drama he doesn’t direct that get’s middling reviews. (We gave it 1 and 1/2 stars out of 5 in our review.) And while IMDB doesn’t have a directorial credit in Eastwood’s future, he’s been putting together a Star is Born remake with Beyonce Knowles and Bradley Cooper for months now.

Are Eastwood’s best days still ahead of him? Or should he have stopped working a while ago? Mack and Sean had differing opinions about the state of Eastwood’s career, so they took it to the Great Debate forums, where they hammered out the specifics of Clint’s past, present and future. Who’s right? Who’s wrong? Read on, and decide!

Sean: Mack, I'm sorry, but given the quality of the last few Clint Eastwood efforts, I'm sticking by my belief that the once-great storyteller really needed to retire a long time ago. And by that, I mean 20 years ago. That's when Eastwood directed his last true masterpiece, Unforgiven. And nothing that he has put out since has come close to matching that film in terms of quality or resonance.

Mack: Retire after Unforgiven? Are you kidding me? Do you realize Clint has been nominated for three directing Academy Awards in just the last decade? I'm willing to admit a few of this more recent movies have dipped in quality a bit, but I'm dumbfounded as to what you could possibly have against Million Dollar Baby, Gran Torino, Mystic River, Bridges Of Madison County, and more?

Sean: Well, Mystic River is terrible. An overwrought mess of button-pushing melodrama marked by Tim Robbins' horrific Bahs-tan accent and a stiff Marcia Gay Harden turn. But I digress, slightly. For while I agree with you that Million Dollar Baby and Bridges are very good movies (probably outstanding movies), they are not compensation for the drivel Eastwood puts out. For every Madison County, Clint saddles us with a Blood Work, Space Cowboys, Invictus, J. Edgar, Changeling (!!) ... the list of bad movies -- flat-out BAD movies -- far outweighs the good that Eastwood has produced in the last 20 years.

The big problem I have with Eastwood is that I don't believe he has anything left to say to an audience. What was Invictus about? Can anyone remember? How about Hereafter? It was moody, but what was the point? I'm asking, honestly, because I think Clint works nowadays because it's what he does. He's in a routine. Much like Woody Allen. Start shooting a script in January or February. Keep the budget down. Work with a "kid" actor who's enamored with Clint's legend (Matt Damon, Angelina Jolie), be in theaters by November or December, and repeat the following year. There's no passion left. Every once in a while, maybe. But not enough to justify the last two decades.

Mack: I reject your claim that Clint has made a lot of bad movies over the past two decades, but I will meet you in the middle and say he's given us a lot of annoyingly mediocre or even below-average movies. To be quite honest, his success ratio is definitely in the shitty range, but since you brought up Woody Allen, let's use that comparison. Like Eastwood, Allen has made a lot of yawners over the past two decades, but last year, he gave us Midnight In Paris. Do you know why that happened? Because a miss or two or even 20 don't suck the talent out of a filmmaker. Someone who has always been talented remains talented, and it's the same way with Clint Eastwood. Unlike an overwhelming majority of directors, he's capable of making a brilliant movie. At any point, we could go to the theater and see something as good as Unforgiven or Madison County or Million Dollar Baby. Doesn't that possibility appeal to you at all? Wouldn't you rather be an optimist?

Sean: I see what you are saying. And I agree, to a certain extent. Eastwood (and Allen) remain capable of greatness. But the misses are soul-crushing experiences that are a chore to get through. J. Edgar was painful. Changeling was actual work. And I can't remember a SINGLE thing about it. Not a one.

Here's what I'd suggest, if you are unwilling to suggest a complete "out to pasture" verdict for Mr. Eastwood. He needs to stop making films annually. Clint hasn't missed very many years since Play Misty for Me back in 1971. I'd urge him to stop. Take a few years off between films. Wait for a script that really moves him. Speaks to him. Gives him a reason to work beyond, "I'm kind of bored and Warner Bros. is willing to fund me." Because yes, I would love to see Eastwood's next Bridges. But I don't want to have to sit through Invictus to get to it.

Mack: I like where your head is. In fact, I'm sure some of the movies Clint has made lately have been less about passion and more about getting out of the house. Unfortunately at 82, I'm not sure how many years he has left. I get that you'd want to remember Clint as a model of consistency and competence. It's never fun to get your hopes up and be disappointed by a director you have a lot of faith in, but based on all the joy he's already brought me, I'll keep going to the theater and giving him a chance. Maybe that makes me stupidly loyal, but I just can't help myself.

Sean: And neither, it appears, can Clint!

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Editor In Chief

Mack Rawden is the Editor-In-Chief of CinemaBlend. He first started working at the publication as a writer back in 2007 and has held various jobs at the site in the time since including Managing Editor, Pop Culture Editor and Staff Writer. He now splits his time between working on CinemaBlend’s user experience, helping to plan the site’s editorial direction and writing passionate articles about niche entertainment topics he’s into. He graduated from Indiana University with a degree in English (go Hoosiers!) and has been interviewed and quoted in a variety of publications including Digiday. Enthusiastic about Clue, case-of-the-week mysteries, a great wrestling promo and cookies at Disney World. Less enthusiastic about the pricing structure of cable, loud noises and Tuesdays.