Actor William H. Macy‘s prolific career has spanned 42 years and counting, as of 2022. He’s the world’s best-known and hardest-working character actor, and it sometimes seems like he pops up in every other movie. He’s worked extensively in television and film and has based his career on quirky characters in independent films. He’s been nominated for an Academy Award for Best Supporting Actor for his role in the 1997 film Fargo. He’s also won two Emmy Awards and four Screen Actors Guild Awards, and was nominated for an Emmy six times for his role in the television show Shameless, in which he played Frank Gallagher from 2011 to 2021.



He hit the height of his career in the 1990s and 2000s appearing in a slew of popular films including Pleasantville, Mr. Holland’s Opus, Benny & Joon, Air Force One, Happy Texas, A Civil Action, Above Suspicion, Ghosts of Mississippi, Jurassic Park III, Panic, Sahara, Boogie Nights, the Gus Van Sant remake of Pyscho, and Welcome to Collinwood, to name just a few.

On a personal front, Macy has been married to actress Felicity Huffman since 1997, and the couple even dated on and off for 15 years prior to getting married. The couple has two daughters Sophia and Georgia, and in 2019, Macy and Huffman were part of the College Admissions Scandal. Huffman paid $15,000 to have someone take the SAT for her daughter Sophia so that she’d have a better chance at getting into the college of her choice. Huffman was indicted on fraud and conspiracy charges and sentenced to 14 days in federal prison, where she served 10. Macy was never charged in the scandal, though it may have affected his career; the actor has only starred in one project in the past five years, the Hulu series The Dropout. Nonetheless, he has a rich and incredible career, and these are the best William H. Macy movies.

8 Magnolia

In 1999. William H. Macy starred as part of the ensemble cast in Paul Thomas Anderson’s drama Magnolia. The film featured interconnected stories about characters involved in the quest for forgiveness, happiness, and meaning in Los Angeles’ San Fernando Valley. The film also starred Tom Cruise, the late Phillip Seymour Hoffman, Julianne Moore, John C. Reilly, and Melora Hardin. It was well received critically and earned Cruise a nomination for Best Supporting Actor at the Academy Awards and a Golden Globe win in the same category. Macy played Donnie, a former What Do Kids Know? champion who finds himself reluctantly embroiled in a crime.

7 Wag the Dog

In 1997, William H. Macy appeared in director Barry Levinson’s political satire Wag the Dog. In the film, a spin doctor (Robert DeNiro) teams up with a successful Hollywood producer (Dustin Hoffman) to make up a fake war in Albania in order to distract voters from a presidential sex scandal. Macy plays CIA Agent Charles Young, who is sent to expose the hoax. However, the spin doctor does his thing and convinces Young that exposing the lie would be against the CIA’s best interests. Film critic Roger Ebert wrote of Wag the Dog, “The movie is a satire that contains just enough realistic ballast to be teasingly plausible; like Dr. Strangelove, it makes you laugh, and then it makes you wonder.”

6 Seabiscuit

William H. Macy appeared as Tick Tock McLaughlin, a racing announcer in writer/director Gary Ross’ 2003 film Seabiscuit. The film is loosely based on the real-life horse of the same name and on the Laura Hillenbrand novel Seabiscuit: An American Legend. Seabiscuit was an undersized Thoroughbred horse who went on to great success despite being overlooked at the beginning of his career. His against-all-odds, zero-to-hero success made him a media sensation during the Great Depression.

RELATED: William H. Macy Joins Shameless Cast in Saying Goodbye to Fans After Series Finale

5 State and Main

David Mamet wrote and directed the 2000 film State and Main which contains a film within a film. William H. Macy plays Walt Price, the director of a film called The Old Mill. The production moves from New Hampshire to Vermont due to the leading man’s (Alec Baldwin) prediction for preying on underage girls. Unfortunately, the new town they are shooting in doesn’t have the mill the film needs, and chaos ensues with the screenwriter (the late, great, Phillip Seymour Hoffman) having writer’s block, and the leading woman (Sarah Jessica Parker) refusing to do the nude scenes she’s contractually obligated for unless she’s paid an additional $800,000. More chaos ensues when the leading man gets involved with a local teenager, forcing a powerful producer to come to town to help Macy’s character sort it all out.

4 The Cooler

In 2003, William H. Macy starred in the title role of The Cooler. As Bernie Lootz, a casino “cooler,” just walking up to a gaming table in a casino breaks the streak of anyone winning and delivers a streak of bad luck for the other players. Lootz obtained this job to his constant bad luck, which makes him suited for the job. He used to be a gambling addict and his job in essence pays off his years of debt. When he gets involved with cocktail waitress Natalie (Maria Bello), his ability to bestow bad luck and cool off tables starts to change. One of the few films which features Macy front and center as a headliner, The Cooler remains one of the best movies about gambling.

3 Pleasantville

In 1998’s Pleasantville, William H. Macy played George Parker in the film from writer and director Gary Ross. Parker is the father in the fictional television show about the seemingly idyllic life in the 1950s town Pleasantville that David (Tobey Maguire) and Jennifer (Reese Witherspoon) find themselves magically transported to. The residents of Pleasantville learn a few things from David and Jennifer, and they also learn some life lessons about how the past isn’t as simple as it seems in this charming movie.

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2 Boogie Nights

William H. Macy starred in another Paul Thomas Anderson movie about Los Angeles’ San Fernando Valley in 1997’s Boogie Nights. The film is about Dirk Diggler (played by Mark Wahlberg), a dishwasher at a nightclub who becomes a successful star in porn films. The story follows the rise of his career in the 1970s and fall of it in the 1980s. Macy played assistant director Bill “Little Bill” Thompson who continuously finds himself being cheated on or disregard both professionally and personally. The film has a stacked cast, including Burt Reynolds, Heather Graham, Don Cheadle, Julianne Moore, and John C. Reilly.

1 Fargo

Fargo is the 1996 dark comedy from Joel and Ethan Coen. William H. Macy starred as a desperate car salesman who hires two criminals to kidnap his wife so that he can collect a ransom from her wealthy father. Frances McDormand played Marge Gunderson, a police chief in Minnesota who is investigating murders that happen after Macy’s character’s crime. The film was nominated for seven Oscars including Best Picture, Best Director, and Best Supporting Actor for Macy. It won two Academy Awards, Best Actress for McDormand and Best Original Screenplay for the Coen brothers.