The term “character actor” can sometimes be an ill-informing one, as it does not suggest that an actor simply isn’t “good enough” to star in leading roles. In the case of William H. Macy, he’s so versatile and experimental of a performer that he can properly depict a variety of characters in all genres of films.

Macy’s most famous work in the past decade has mostly been on television, thanks to his recurring role on Shameless, but he has often been a favored actor by leading directors like the Coen Brothers and Paul Thomas Anderson. These are the ten best William H. Macy movies.

10 'Wag the Dog' (1997)

wag the dog movie image
Image via New Line Cinema

Wag the Dog is a brilliant political satire from Barry Levinson that makes bold predictions about the future of American media and politics that now seems rather tame in comparison to reality.

When the President of the United States is caught having an affair, the Oval Office advisor Winifred Ames (Anne Heche) recruits the spin doctor Conrad Brean (Robert De Niro) and the Hollywood producer Stanley Motss (Dustin Hoffman) to put together a “fake war” to divert voters’ attention before the election. In a film filled with various political figures, Macy has a particularly humorous role as the nonplussed CIA Agent Charles Young.

9 'Boogie Nights' (1997)

William H Macy as Little Bill in Boogie Nights
Image Via New Line Cinema

Boogie Nights is one of the funniest and most heartwarming films of the 1990s, as it celebrates the communal aspects of performers filming together like a family unit, even if what they’re making is pornography. However, that doesn’t mean that the film doesn’t wrestle with some dark themes and features some very disturbing moments.

Macy appears in a devastating role as Jack Horner’s (Burt Reynolds) assistant director Little Bill Thompson, who dies by suicide upon witnessing his wife having an affair with one of his film’s stars at a New Year’s Eve party.

8 'A Civil Action' (1998)

John Travolta as Jan Schilichtmann in A Civil Action

A Civil Action is a great example of the type of movie that Hollywood doesn’t make anymore: the ‘90s courtroom thriller. The film focuses on the hotshot Boston personal injury attorney Jan Schlichtmann (John Travolta), who discovers that the water supply in the small community of Woburn, Massachusetts, is being polluted by the corporations Beatrice Foods and W. R. Grace and Company.

Macy has a powerful role as James Gordon, a local lawyer who struggles to see how Jan’s “big city” approach will apply to the legal system of a small town.

7 'Mystery Men' (1999)

Mystery Men (1999)  (1)

Even if audiences are having a little bit of superhero fatigue, one film within the genre that actually deserves to be continued is the original 1999 comedy Mystery Men. The quirky satire of comic book movies focuses on an offbeat group of superheroes with unusual powers led by the rage-induced hero Mr. Furious (Ben Stiller).

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Macy plays one of the film’s scene stealers, the superhero known as “The Shoveler,” who replaces traditional weapons like guns or swords with a good, old-fashioned shovel:From he’s not exactly the dark and brooding type.

6 'Room' (2015)

William H Macy in Room

Macy is a master of having a limited amount of screen time and maximizing it; while he doesn’t appear in the Oscar-winning 2015 drama Room until the second hour of the story, he has an unforgettable role that helps seal the tragedy of the story.

Macy appears as Robert Nesome, the heartbroken father of the kidnapped woman Joy (Brie Larson), who reunites with his daughter after she finally escapes from her captor after spending the majority of her youth in captivity. Macy has a heavy heart and cannot even bear to look at Joy’s son Jack (Jacob Tremblay).

5 'Pleasantville' (1998)

William H Macy in Pleasantville

Pleasantville has a brilliant premise; when the bickering teenage siblings David (Tobery Maguire) and Jennifer (Reese Witherspoon) are transported into the world of a 1950s sitcom (also called Pleasantville), they begin to invade the black-and-white reality with their modern ideas and fight against the show’s perpetration of small town ideas.

Macy has an amusing role as the spineless husband George Parker, who is taken aback by his wife Betty’s (Joan Allen) sudden changes as she experiences sexual pleasure for the first time. George and Betty’s marriage goes from contentious to sincere throughout the film.

4 'Seabiscuit' (2003)

William H Macy in Seabiscuit

Seabiscuit is a good, old-fashioned inspirational racing story that follows the small-town boy Red Pollard (Tobey Maguire) and his trainer Tom Smith (Chris Cooper) as they prepare to lead the titular horse to victory in a major Thoroughbred horse race amid the American economic depression of the 1930s.

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The film is expertly designed with period-accurate details that reflect the era. Among the fun callbacks to the ‘30s is Macy’s performance as the announcer "Tick Tock" McLaughlin, who narrates the races. Macy received a Golden Globe nomination for Best Supporting Actor for his performance.

3 'Magnolia' (1999)

William H Macy as Donnie

Magnolia is perhaps the most ambitious film of Paul Thomas Anderson’s career, which given his remarkable filmography, is no small statement. The three-hour-long dramatic epic explores the lives of various outsiders, miscreants, and emotionally damaged people in the San Fernando Valley whose lives begin to intersect and cross over.

Macy appears in a heartbreaking supporting role as Donnie Smith, a former child star on the game show What Do Kids Know? whose winnings were stolen by his parents when he was young. The loss of childhood innocence is a major theme that Magnolia wrestles with.

2 'The Cooler' (2003)

The Cooler (2003) (1)

While he’s often cast in supporting roles, Macy did get the chance to play a lead character in the underrated 2003 gambling thriller The Cooler. He stars as Bernie Lootz, a Las Vegas “cooler” whose bad luck seemingly assures other gambling participants to keep playing.

However, Bernie’s luck begins to turn around when he meets the cocktail waitress Natalie Belisario (Maria Bello) and instantly falls in love with her. The romantic chemistry between the two is very charming, considering Macy’s self-deprecating sense of humor.

1 'Fargo' (1996)

William H. Macy in Fargo
Image Via Gramercy Pictures 

Macy’s lone Oscar nomination came in the Best Supporting Actor category for his performance in the 1996 dark comedy classic Fargo. Macy appears as Jerry Lundegaard, the selfish husband who arranges his wife’s staged kidnapping to score some extra cash.

While not as outwardly cruel as the character played by Steve Buscemi, Jerry perfectly represents the corruptive nature of greed and the violence that can be spurred by it. Jerry is one of the film’s most villainous characters, and his sheepish attitude makes him more unlikeable.

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