Clint Eastwood is retired. That is, according to his son. “I have many fond memories of working with him,” musician and composer Kyle Eastwood said in November, in concert footage that’s gone viral this week. “Now he’s retired, he’s 95 years old. But I was very lucky to be able to work with him on quite a few films. It was a great experience for me.”

Way to bury the lede, Kyle! Eastwood hasn’t officially confirmed his retirement, but if he has indeed brought his filmmaking career to a close, presumably to stare into the middle distance on a farm somewhere (that feels very Clint, doesn’t it?), it’d mean 2024’s Juror #2 – a legal thriller starring Nicholas Hoult and Toni Collette – was his curtain call.

And it would also bring to a close a career as defined by its mad diversity (Unforgiven, The Good, the Bad and the Ugly, Letters from Iwo Jima AND that action comedy with the orangutang?) as it is Eastwood’s vague ambiguity as a celebrity. Just what is he like? Is he funny? Stern? Intimidating?

Luckily, many of the actors who’ve worked with him over the years have shared quirky anecdotes about the man in question. We’ve gathered a handful of them in the hopes of getting to the bottom of him.

Tom Hanks in ‘Sully’open image in gallery
Tom Hanks in ‘Sully’ (Warner Bros)

Laura Linney and Tom Hanks

Both Laura Linney and Tom Hanks have shared insights into working with Eastwood over the years.

The pair, who starred in 2016 drama Sully: Miracle on the Hudson, were left feeling relaxed by the director’s gentle filmmaking approach.Speaking to The Independent for new interview series Life in Pictures, Linney – who also worked with Eastwood on Absolute Power (1997) and Mystic River (2003) – revealed that his hesitancy to shout on sets stems from his experiences working on westerns, including Rawhide.

“He talks in that level voice. He stands next to the camera, watches the scene, goes, ‘OK you can stop. Did you feel good about that? I felt good about that. Were we in focus? OK, we can move on.’ That’s how he rolls. The reason he doesn’t yell ‘action’ or ‘cut’ is because of the westerns he made. Because if someone yelled, the horse would jump and get scared, so everybody’s quiet on set.

“Because we all have nervous systems and it’s true – when someone screams ‘action’, particularly if it’s a scene where you have to concentrate, it takes a little time to recover from that.”

Hanks concurred, once stating on The Graham Norton Show: “What’s it like working with Clint? He treats us like horses.”

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François Pienaar, Matt Damon, Clint Eastwood and Morgan Freeman at the London premiere of ‘Invictus’open image in gallery
François Pienaar, Matt Damon, Clint Eastwood and Morgan Freeman at the London premiere of ‘Invictus’ (Getty Images)

Morgan Freeman

Morgan Freeman, who starred in Eastwood’s Oscar-winning films Unforgiven (1992) and Million Dollar Baby (2005), felt Eastwood’s experiences as an actor made him a better filmmaker – so much so that everyone often comes away thinking he’s the best director they’ve ever worked with.

“He doesn’t fool around with actors,” he once told US interviewer Larry King. “He hired you to do that job, so he ain’t doing it for you. He respects the actor. Everybody who’s ever worked with him comes away with that feeling – that this guy tops.”

Meryl Streep

When Clint Eastwood wanted Meryl Streep to star in 1995 romance drama The Bridges of Madison County, the studio didn’t approve of his decision – despite the then 45-year-old being the same age as the character she was playing. Eastwood pushed back. “Clint made a, I gather, case for me, which I was glad about,” she said in a documentary about the making of the film, adding: “And I would certainly have made a case for him.”

Clint Eastwood and Angelina Jolie in 2008open image in gallery
Clint Eastwood and Angelina Jolie in 2008 (Getty Images)

Angelina Jolie

Angelina Jolie was “terrified” about the prospect of working with Eastwood due to his renowned one-take policy, but the actor felt she delivered a better performance in 2008 drama Changeling as a result. “He’s famous for shooting just one or two takes, but because of that, you know he’s not going to drain you emotionally,’” she told Indie London.

“He’ll be very prepared from the moment you walk in the door, and so you have this feeling of having to bring your all, but if you bring your all and give it everything you’ve got until you’re emotionally drained. He will capture it on film and he won’t ask you to do it 20 times. So, it does allow for you to really push yourself. And because he does do everything in one take, everything is very fresh.”

Matt Damon

Damon worked with Clint Eastwood on 2009 sports drama Invictus – and was forced to get used to the director’s quick-paced groove after “testing the theory” that he only likes one take. Speaking on First We Feast, Damon explained: “We did the first take. It went pretty well. Clint says, ‘Cut, print, check the gate,’ which means we’re gonna move on. And I said, ‘Hey, boss, maybe you think we could get one more?’ He just turned and goes, ‘Why? Do you want to waste everybody’s time?’ Damon worked with Eastwood again in Hereafter (2010).

Jeff Daniels

Actor Jeff Daniels revealed a softer side of Eastwood after they worked together on the thriller Blood Work in 2002, recalling that the filmmaker quelled his nerves when he appeared anxious on the set. He was playing an alcoholic detective in the film, and admitted to Eastwood that he wasn’t sure he could do it.

“I’m walking down the set with Clint Eastwood, and Clint said, ‘If you can do [the 1996 black comedy] 2 Days in the Valley and you can do [the deeply stupid 1994 comedy] Dumb & Dumber, you can do this,’” Daniels recalled.

Which is nice! But Daniels also added, during this appearance on Stephen Colbert’s talk show in 2021, that he and Eastwood had an earlier interaction which spoke volumes about Eastwood’s apparent love of gross-out humour. Cornering him at a celebrity golf tournament, Eastwood expressed to Daniels his admiration for Dumb & Dumber.

“Eastwood comes walking across the breakfast tent and he’s looking right at me,” Daniels remembered. “And he [says], ‘Jeff Daniels. I saw Dumb & Dumber. The toilet scene — that happened to me.’ He started laughing and turned around and walked away.”

For the uninitiated, the scene in question saw Daniels’s character unknowingly drinking laxatives and being forced to evacuate his bowels in the home of a woman he’s attracted to. The more you know!

Clint Eastwood, Amy Adams and Justin Timberlakeopen image in gallery
Clint Eastwood, Amy Adams and Justin Timberlake (Getty Images)

Justin Timberlake and Amy Adams

For a scene in Eastwood’s 2012 film The Trouble with the Curve, Justin Timberlake was asked to clog dance with his co-star Amy Adams – which Eastwood was all for, despite Timberlake having difficulty breaking out the moves.

“Gene Kelly he wasn’t,” Eastwood told USA Today. Asked if he, too, would clog dance to woo a lady, Eastwood expressed his enthusiasm. “If there’s a great looking gal that you’re hitting on and she wants to clog, well then, OK… clog.”

“We actually couldn’t get the clogs off him,” Timberlake added… jokingly? Maybe? Maybe not?

“And they were Amy’s,” Eastwood replied. “I borrowed them.”

So there you have it. Clint Eastwood: taciturn Hollywood icon and amateur clog dancer.

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