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Top 5 Clint Eastwood Movies and ‘Cry Macho’

September 17, 2021/ 89 min/ Sean Fennessey · Adam Nayman · Chris Ryan

Sean Fennessey, Adam Nayman, and Chris Ryan spend an episode on all six decades of Clint Eastwood: 'Cry Macho,' the mythos around him, and a shared, unanimous No. 1.

24 films across 5 segments.

AI-generated This episode was transcribed and analyzed with AI models. The matches aren't perfect — expect the occasional misheard title or a link to the wrong film.

Review: Cry Macho

Cry Macho poster

Cry Macho 2021

Eastwood, 91, directs and stars as a washed-up ranch hand sent into Mexico to retrieve his old boss's son (and a prize fighting rooster). The project sat unmade for over thirty years, with Robert Mitchum, Burt Lancaster, Pierce Brosnan, and eventually Arnold Schwarzenegger all attached before Eastwood finally made it himself.

Sixty years, one personathe shape of a career

Play Misty for Me poster

Play Misty for Me 1971

Eastwood's directing debut, released the same year as Dirty Harry, a DJ-stalker thriller the group calls a clear precursor to Fatal Attraction.

Dirty Harry poster

Dirty Harry 1971

The Don Siegel film that made Eastwood's persona. Adam calls the “do you feel lucky” scene a performance built on total numbness, credited alongside Bullitt as a direct inspiration for the inspector Ruffalo plays in Zodiac.

The Outlaw Josey Wales poster

The Outlaw Josey Wales 1976

Cited as a direct influence on Tarantino's screen violence, though Adam notes Tarantino only ever namechecks Leone, never Eastwood himself.

Flags of Our Fathers poster

Flags of Our Fathers 2006

Adam's example of a film Eastwood directed that isn't “about” Clint Eastwood, unlike Gran Torino or The Mule.

Mystic River poster

Mystic River 2003

Another one Adam says isn't really “about” Clint Eastwood, despite being one of his biggest awards-season hits.

Gran Torino poster

Gran Torino 2008

Definitely about Clint, per Adam, and a movie he says friends have “literally threatened his life” over him not loving enough.

The Mule poster

The Mule 2018

The direct forerunner to Cry Macho the group keeps circling back to, including its own long stretches of just watching Clint drive.

Sean Fennessey's Fivefavorite Clint Eastwood movies

Unforgiven poster
No. 1

Unforgiven 1992

No. 1 - the unanimous pick across all three lists. Sean singles out the opening shot of Eastwood digging his wife's grave, and a David Webb Peoples screenplay that sat unproduced for a decade before Eastwood finally made it.

Magnum Force poster
No. 2

Magnum Force 1973

No. 2 - the Dirty Harry sequel Eastwood made as a direct answer to the original's police-brutality backlash, directed by the “fairly unheralded” Ted Post.

Escape from Alcatraz poster
No. 4

Escape from Alcatraz 1979

No. 4 - directed by Don Siegel; Eastwood has fewer than 100 lines in the whole movie and still anchors every frame.

High Plains Drifter poster
No. 5

High Plains Drifter 1973

No. 5 - the ghost-stranger revenge Western where a town gets painted red to draw out its killers. Paired here with its unofficial 1985 sequel, Pale Rider.

Adam Nayman's Fivefavorite Clint Eastwood movies

Unforgiven poster
No. 1

Unforgiven 1992

No. 1 - unanimous. The film Adam's been measuring every subsequent Eastwood “victory lap” against since the top of the episode.

The Beguiled poster
No. 2

The Beguiled 1971

No. 2 - an audible away from Dirty Harry, made by the same director (Don Siegel) the same year. Adam calls it Dirty Harry's mirror image: instead of all-powerful, Eastwood spends the whole movie humiliated. Sofia Coppola remade it in 2017.

The Bridges of Madison County poster
No. 3

The Bridges of Madison County 1995

No. 3 - “an extraordinary act of transubstantiation” out of a book Adam thinks is bad, built around the scene where Eastwood picks Meryl Streep a bouquet of poisonous flowers.

A Perfect World poster
No. 4

A Perfect World 1993

No. 4 - Kevin Costner as the escaped convict Eastwood's Texas Ranger chases down. Adam calls it a dry run for Cry Macho's mentor-and-kid template, and one of the best-made movies Eastwood has directed.

The 15:17 to Paris poster
No. 5

The 15:17 to Paris 2018

No. 5 - a deliberate provocation: a dramatization of a real train terror attack starring the actual men who stopped it, not actors. Adam calls it “the weirdest damn movie” and admits he's the only one of the three who'd watch it twice.

Chris Ryan's Fourfavorite Clint Eastwood movies

Unforgiven poster
No. 1

Unforgiven 1992

No. 1 - unanimous. Chris credits Gene Hackman's villain, who doesn't think of himself as one, and a beating that finally showed him what movie violence actually looks like, after years of his dad debunking barroom-brawl clichés.

For a Few Dollars More poster
No. 2

For a Few Dollars More 1965

No. 2 - Chris's favorite of the Leone trilogy, for Klaus Kinski above all.

In the Line of Fire poster
No. 3

In the Line of Fire 1993

No. 3 - Wolfgang Petersen's Secret Service thriller, which Chris calls the best acting of Eastwood's career, built on the phone scenes with John Malkovich and a gentler Rene Russo romance than the usual Eastwood age-gap dynamic.

Thunderbolt and Lightfoot poster
No. 4

Thunderbolt and Lightfoot 1974

No. 4 - Michael Cimino's bank-robbery caper with an Oscar-nominated Jeff Bridges, which Chris calls the closest Eastwood ever got to Malick.

Also mentioned raised along the way

Eastwood deep cuts Coogan's BluffEvery Which Way But LooseAny Which Way You CanBronco BillyThe Eiger SanctionPink CadillacThe EnforcerTightropeAbsolute PowerHereafterInvictusJersey BoysTrouble with the CurveThe ChangelingJ. EdgarAmerican SniperSullyRichard JewellA Fistful of DollarsThe RookiePale Rider

Not Eastwood, but in the conversation The Card CounterFatal AttractionCliffhangerZodiacBullittThe Silence of the LambsThe Quick and the DeadRio BravoE.T. the Extra-TerrestrialLincolnFree GuyHeaven's GateField of DreamsJFKThe Bodyguard

In passing Repo ManDeadpoolMajor League II

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