The finalDirty HarrymovieThe Dead Poolwas on a bad note to end the iconic series - butSin Citytechnically provided a better finale for the character.TheDirty Harrymoviesfirmly cemented Clint Eastwood as an A-lister, with the star occasionally picking up Harry’s .44 Magnum for sequels throughout the 1970s and 1980s.The onlyClint Eastwood-directedouting was 1983’sSudden Impact, the fourth (and darkest) of the saga. The star retired the character following 1988’sThe Dead Pool, and the series has been dormant ever since.

It’s likely to remain that way since it’s almost impossible to imagine anyonebutClint in that role. While none of the follow-ups measured up to Don Siegel’s original,The Dead Poolwas the most disappointing of all. The fifth entry was a murder mystery about a serial killer picking victims off the titular list, but outside a creative chase involving a toy car, it was a weak sauce sequel. It looks and feels like a TV movie, Eastwood appears checked out, and it’s a long way from where the franchise began.

Collage of Clint Eastwood as Harry Callahan from the Dirty Harry movie series and Sondra Locke as Jennifer Spencer in Sudden Impact

The Only Killer Clint Eastwood’s Dirty Harry Let Go Free (& Why)

There weren’t many criminals who survived encountering Clint Eastwood’s Dirty Harry, but only one of the movies saw him let a killer go free.

Bruce Willis' Hartigan picked up Dirty Harry’s .44

While he might not be called Dirty Harry,Sin City’sHartigan (Bruce Willis) from “That Yellow Bastard” is very much in the same mould. The character is introduced rescuing a young girl named Nancy from a predatory serial killer - only to be framed and sent to prison for the latter’s crimes. “That Yellow Bastard” revels in its pulp detective fiction and film noir influences, butWillis' Hartigan is clearly a riff on Eastwood’s Dirty Harrytoo.

The structure of the story has many similarities to the originalDirty Harry. Both involve a renegade cop chasing a depraved killer andthe opening sequence of “That Yellow Bastard” feels like it recreates the finale ofDirty Harrywhere Hartigan confronts a wounded Junior (Nick Stahl) on a dock. The two detectives share an unwavering commitment to doing the right thing too and don’t mind breaking rules to see that done.

Bruce Willis as Hartigan carries a 44 magnum in Sin City

Jessica Alba’s Nancy Callahan is another Frank Miller tip of the hat toDirty Harry,as the title detective’s full name is Harry Callahan.

It wouldn’t be hard to see “That Yellow Bastard” functioning as a closing chapter for Eastwood’s Harry. There could only be so many times Harry ignored the law to dispense his version of justice before it caught up to him, or he crossed the wrong people. Sadly,The Dead Poolexplored none of that and instead slotted Eastwood’s detective into a limp procedural. “That Yellow Bastard” understands Harry’s ending wouldn’t be a happy one, but at least he would choose to do things on his terms.

Roark holding up a knife in That Yellow Bastard in Sin City

“That Yellow Bastard” Was Written As A Response To The Final Dirty Harry

Frank Miller is a fan ofDirty Harryand was motivated by his disappointment withThe Dead Poolto write his own finale. Hartigan actually seems like a happier character than Harry when introduced inSin City; he’s happily married and only a day away from retirement. Despite knowing that rescuing Nancy in the opening scene will likely ruin his life, he’s not going to let a child die.TheDirty Harryfilms never played with their formula in any meaningful way, with Harry remaining in the force despite breaking the ruleson countless occasions.

1971

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$36 million

1973

Sin City Movie Poster

$44.6 million

1976

$46.2 million

1983

$67.6 million

1988

Buddy Van Horn

$37.9 million

Having Harry framed and sent to prison would have been a perfect final chapterfor the character, where he was fully abandoned by the force and became a total vigilante. “That Yellow Bastard” understands Harry as a character better thanThe Dead Poolever does, and that he wouldn’t necessarily go peacefully into the night.

Eastwood managed to get numerous pet projects made during his time with Warner Bros by peppering his filmography with very commercial projects. More personal outings likeClint’s favorite Western of his ownBronco BillyorBirdwould be bankrolled by action or thriller fare likeFirefoxorThe Rookie. When it came to gettingBirdproduced, Eastwood agreed to makeDirty Harryand that’s howThe Dead Poolcame together. Again,the sequel has a creative sequence where Harry and his partner are chased by an explosive toy car, but that’s the only scene that stands out.

Sin City’s “That Yellow Bastard” isn’t without its own faults but it’s so much more satisfying as a final tale for “Dirty” Harry Callahan

The bulk of the story is a limp remake of the original, where Callahan chases a killer targeting celebrities who are part of a list - Harry included. There’s also a romantic subplot where Harry romances a reporter played by Patricia Clarkson, but while Eastwood and Clarkson have decent chemistry,The Dead Poolis too lightweight to feel like a trueDirty Harrysequel. It takes swipes at the media and the film business, but lacks most of the grime or food for thought previous entries offered.

Clint himself is visibly disengaged and the finale is too darn silly. It’s not like the series was ever conceived to tell a complete arc for the character, but if Eastwood knewThe Dead Poolwould be the end, it’s a shame he couldn’t have picked a tougher, darker story.Sin City’s"That Yellow Bastard" isn’t without its own faults - especially the icky romance between Hartigan and the older Nancy - but it’s so much more satisfying as a final tale for “Dirty” Harry Callahan.

Dirty Harry

Cast

Clint Eastwood stars in the western Dirty Harry as a no-nonsense San Francisco cop who takes the law into his own hands in pursuit of a serial killer, Scorpio. Directed by Don Siegel and featuring a memorable score by Lalo Schifrin, the film is known for its iconic catchphrases and intense action scenes, and has influenced countless films and TV shows in the years since its release.

Sin City

Based on the original graphic novel by Frank Miller, Sin City is a dark and gritty crime-noir action movie that tells several different stories, all set at the same time in the same city. The lines of good and evil are blurred, with vigilantism being the new norm, as a city rife with corruption slowly swallows its citizens whole. Each protagonist is loosely connected to one another’s stories as the movie paints a bigger picture through each new point of view.