Clint Eastwoodhas been turning in stellar work since the 1960s and, at 94 years old, he’s still at it, with his next movie,Juror No. 2, set for release in October. Over all these decades, he has worked on both sides of the camera and in a host of genres, from action and Westerns to romance and mysteries. Not all of his movies are great, of course, but the best of them rank among some of the finest ever made.

The 1990s were something of a mixed decade for Eastwood, quality-wise. It included some of his biggest box office flops, likeTrue Crime, and his most critically reviled efforts (The Rookie), alongside one of his most touching movies (The Bridges of Madison County) andperhaps his very best(Unforgiven). A few of the failed experiments from this era are even worth checking out for their uniqueness. With this in mind, here are Eastwood’s ten best projects from the 1990s, ranked.

‘The Rookie’ (1990) 1

10’The Rookie' (1990)

Directed by Clint Eastwood

“There’s gotta be a hundred reasons why I don’t blow you away. Right now I can’t think of one.”

Not to be confused with the comedy show starringNathan Fillion, The Rookie sees Eastwood playing veteran cop Nick Pulovski, who’s teamed up with newbie David Ackerman (Charlie Sheen). The mismatched duo is assigned to bring down a notorious car theft ring led by a ruthless criminal. As Pulovski mentors Ackerman, they face dangerous pursuits and intense action scenes while dealing with their personal demons.

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This is very much the weakest of Eastwood’s ’90s output.Not abysmal, but formulaic, at times slow, and shallow, recycling buddy cop tropes. Some of the stunts are decent, but they’re not enough to justify a viewing. Even more surprisingly, the movie was directed by Eastwood himself, but he just didn’t seem particularly committed or inspired.The Rookiereceived muted reviews and made a loss at the box office, in part because it was competing with mega-hitHome Alone.

The Rookie

A gritty crime thriller featuring Nick Pulovski, a seasoned detective who is paired with David Ackerman, a green and eager rookie. Tasked with dismantling a powerful car theft syndicate, the duo faces numerous obstacles, including internal conflicts and dangerous criminals. Nick’s tough-as-nails approach contrasts with David’s idealism, leading to tension and growth as they navigate the perilous assignment. When Nick is captured by the gang, David must rely on his training and instincts to rescue his partner and bring the criminals to justice.

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9’Casper' (1995)

“If I were alive, would you go to the Halloween dance with me?” This one is a bit of a stretch, sinceEastwood only appears in a cameo, butCasperdeserves mentioning as one of Eastwood’s stranger project choices of this decade. Based on the beloved comics character, the movie revolves around the amiable apparition (voiced byMalachi Pearson), who lives in a haunted mansion with his mischievous uncles.Christina Riccico-stars as Casper’s friend and love interest, Kat.

Eastwood shows up at one point as one of the faces that the ghost of Dr. James Harvey (Bill Pullman), morphs into during a humorous mirror scene. The others areRodney DangerfieldandMel Gibson, who also appear as themselves. The movie itself is mediocre (though it’s notable for being the first to havea fully CGI main character) and is an indication of just what a mixed bag the 1990s were for Eastwood.

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An afterlife therapist and his daughter meet a friendly young ghost when they move into a crumbling mansion to rid the premises of wicked spirits.

8’White Hunter Black Heart' (1990)

“You’re way too beautiful to interrupt people.” Things improve significantly withWhite Hunter, Black Heart. Here, Eastwood directs and stars as John Wilson, a director obsessed with hunting elephants while on location in Africa. Loosely based on the life of filmmakerJohn Huston, the movie delves into Wilson’s reckless behavior and his growing detachment from his film project in favor of his personal obsession. His drive for hunting glory places his colleagues at risk, while revealing deeper cracks in his psyche.

Eastwood does a great job at mimicking Huston’s voice and mannerisms, while also making the fictionalized character of Wilson both repellent and charming. For the movie to work, the viewer has see Wilson as a complex figure rather than just a villain, and Eastwood succeeds at conveying that. The film is not an unqualified triumph, but it’s probably underrated, with Eastwood pushing himself into new storytelling territory as a director. It’s worth watching even just as a glimpse inside his artistic evolution.

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7’Midnight in the Garden of Good and Evil' (1997)

“This place is fantastic. It’s likeGone With the Windon Mescalin.“Midnight in the Garden of Good and Evilis a sprawling Southern Gothic examining the lives of various characters in Savannah, Georgia. The main character is out-of-town journalist John Kelso (John Cusack) who travels to the city cover a grand Christmas party hosted by wealthy art dealer Jim Williams (Kevin Spacey). However, the story spirals intoa murder mysteryas Williams is accused of killing his lover. Some of the plot developments that follow seem a little melodramatic, though most are actually factual.

Although flawed,this is certainly one of Eastwood’s most unique efforts as a director, fusing elements of thriller, drama, nonfiction, and even a touch of horror. Some of the courtroom scenes get tiresome, but rich atmosphere and engaging storytelling keep the plates spinning. Finally, the talented cast does the rest of the heavy lifting, including from supporting playersJack Thompson,Jude Law, and the director’s daughter,Alison Eastwood.

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6’True Crime' (1999)

“When my nose tells me something stinks, I gotta have faith in it.” In this one, Eastwood plays Steve Everett, an investigative reporter with a reputation for being a loose cannon. Assigned to cover the execution of convicted murderer Frank Beechum (Isaiah Washington), Everett begins to uncover evidence that suggests the man may be innocent. He races to clear Beechum’s name, but his own inner demons threaten to be a stumbling block.

The central plot is a fairly generic, and never quite builds up into the gripping mystery it hopes to be. Nevertheless,the characterization is great, with subplots and quiet, emotional moments elevatingTrue Crimeabove other, more mediocre movies. For example, Everett’s alcoholism and strained relationship make him more interesting than the typical protagonist in this kind of film. Overall,True Crimeis fine without being amazing, and failed to connect with audiences on release. It grossed just $16.6m against a budget of $55m.

True Crime

True Crime follows journalist Steve Everett as he races against time to uncover the truth about a Death Row inmate he believes is innocent. Amidst personal flaws and professional obstacles, Everett must meticulously piece together evidence to expose potential miscarriage of justice before the execution deadline.

5’Absolute Power' (1997)

“When you’re alone at night, and your rage takes over and you want an avenger, what face do you put with your enemy?” In this action thriller, Eastwood is Luther Whitney, a skilled thief who witnesses a murder during a high-profile robbery. The twist? The murder involves the President of the United States (Gene Hackman), and a cover-up ensues. Luther finds himself caught in a deadly game of cat and mouse, as both the government and law enforcement hunt him down.

One’s enjoyment of Absolute Power comes down to whether the viewer is able to accept the wacky premise. A number of developments are far-fetched and there are more than a few plot holes.It’s either a goofy misfire or a more interesting take on action tropes, depending on the audience. That said, the star power is considerable. Eastwood and Hackman are great, as areEd HarrisandLaura Linney.

Absolute Power

Luther Whitney, a master thief, witnesses a murder involving the President of the United States during a heist. As he becomes a target of a massive cover-up, Luther must navigate a dangerous web of lies and corruption, using his skills to expose the truth while staying one step ahead of those who want him silenced​.

4’In the Line of Fire' (1993)

Directed by Wolfgang Petersen

“God doesn’t punish the wicked and reward the righteous. Everyone dies.” WhereAbsolute Powerfalls short of its potential,In the Line of Firelives up to its own in practically every way. It sees Eastwood taking on the role of Secret Service agent Frank Horrigan, haunted by his failure to prevent the assassination ofPresident Kennedy. Decades later, Horrigan is called back into action when a former CIA assassin (John Malkovich), plots to kill the current president.

The finished product is a stellar action thriller, nimbly directed byWolfgang Petersen(Das Boot,The NeverEnding Story). While Eastwood is compelling, the true highlight is Malkovich. Here, he turns in a fantastic villain performance that earned him a Oscar nomination for Best Supporting Actor. He’s alternately cold and explosive, bouncing between the sangfroid of Hannibal Lecter and the violence of Leatherface. His delivery is careful and robotic, charismatic without being over-the-top, and consistently scene-stealing.

In the Line of Fire

3’A Perfect World' (1993)

“Never underestimate the kindness of the common man.” Eastwood directs and co-stars in this crime drama, which isone of his very best projects.Kevin Costnerleads the cast as escaped convict Butch Haynes, who kidnaps a young boy (T.J. Lowther) during his escape, and forms an unlikely bond with the child, leading to a complex and emotional journey. Eastwood appears as the Texas Ranger trying to track Haynes down.

A Perfect Worldalmost feels like a neo-Western. The manhunt provides the driving force of the narrative, but the film also explores the psychology of the main characters in detail. In this regard,it’s an unusually reflective crime film, making comments about criminality, the child welfare system, corrupt authorities, and the criminal justice system in general. The central themes are regret, guilt and destiny, with masculinity also placed under the microscope. Eastwood’s fans who haven’t seen it yet ought to check it out.

A Perfect World

A kidnapped boy strikes up a friendship with his captor, an escaped convict on the run from the law, while the search for him continues.

2’The Bridges of Madison County' (1995)

“This kind of certainty comes but just once in a lifetime.” On the more romantic end of the spectrum is The Bridges of Madison County, in which Eastwood appears as Robert Kincaid, a National Geographic photographer who embarks on a brief yet life-changing affair with Francesca Johnson (Meryl Streep). It’s both warm and poignant, delving deep into the protagonists as well as the secondary characters, looking at how the affair affects everyone involved.

Though perhaps overly sentimental at times, the movie is enjoyable and more graceful than it might have been in the hands of a lesser director. He captures the quiet beauty of the setting, aided by a gorgeous score byLennie Niehaus.Streep’s presence helps things a lot, and she’s phenomenal as usual. Her work earned the movie its lone Oscar nomination. Overall,The Bridges of Madison Countymakes for Eastwood’s sweetest and most tender project, and it’s certainly not without its charms.

The Bridges of Madison County

Photographer Robert Kincaid wanders into the life of housewife Francesca Johnson for four days in the 1960s.

1’Unforgiven' (1992)

“I’ve killed just about everything that walks or crawled at one time or another. And I’m here to kill you.” When it comes Eastwood’s best movie of the 1990s, nothing can topUnforgiven, which is not only one of the strongest films of that decade but one ofthe greatest Westerns of all time. Here, Eastwood is William Munny, a retired outlaw who is pulled back into his violent past when he takes on one last job to avenge an assaulted woman. Alongside his old partner, Munny wrestles with his conscience as he confronts the brutal reality of his actions.

This is a revisionist tale, deconstructing many myths of the Old West and consistently challenging the audience’s perceptions.It also plays neatly on Eastwood’s storied history in the genre, making it a role that only he could truly play. Munny and all the major characters are complex, with the film deftly dealing in ambiguities and moral shades of gray.

Unforgiven

Retired Old West gunslinger William Munny reluctantly takes on one last job with the help of his old partner Ned Logan and a young man, The “Schofield Kid.”

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