Top 10 Comedy Directors of the 90s (2023)

July 6, 2022 by Jonah Rice In 1990s, Movies Leave a comment

With this list, I’m mainly looking for consistency. Guys like Jonathan Lynn who put out a single hit sandwiched between a bunch of lead balloons won’t meet my criteria. One, maybe two bad-to-mediocre movies is fine, as long as the director made up for it with an equal number of films that fall on the opposite end of the spectrum.

With those qualifications in mind (which, of course, are really just my opinions) along with critical consensuses, box office results, accolades at the Oscars, and preservation in the National Film Registry, these are the ten best comedy directors of the 1990s.

Also, I’m omitting guys like John Lasseter—while Toy Story and A Bug’s Life were huge on laughs, those categorize as animated movies. Different list for a different time.

Top 10 Comedy Directors of the 90s (1)

10. Charles Shyer

As charming as The Parent Trap remake was from 1998, Charles Shyer made one of the worst films you’ll see on this list: I Love Trouble in 1994, starring Julia Roberts and Nick Nolte. Torn apart by fans and critics alike, it’s probably the worst effort of Shyer’s career.

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However, I’d say he made up for it with the aforementioned Parent Trap, along with both Father of the Bride movies starring Steve Martin. We’ll be showing those to our kids for generations to come.

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9. Barry Sonnenfeld

Although responsible for the inadequate Wild Wild West, Sonnenfeld provided us with four of the genre’s absolute best, starting with both The Adams Family and Adams Family Values. Those movies aged wonderfully, and when you add a couple of more hits like Get Shorty and Men in Black, Sonnenfeld was killing it before Wild Wild West entered the fold.

He also directed For Love or For Money, and it was exactly okay, so, not much to add there.

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8. Tom Shadyac

Patch Adams was a pretty pathetic project, Ace Ventura: Pet Detective is what it is, and The Nutty Professor was solid enough, but luckily for Shadyac, his magnum opus splashed into theaters toward the latter half of the decade.

With Jim Carrey in the starring role, Liar Liar was among the ten highest-grossing movies of 1997 and garnered tremendous critical scores, with many citing it as the best performance of Carrey’s career to that point. Which, it undoubtedly was. It’s aged perfectly, too, and made up for the only true blemish on Shadyac’s resume—that’s you, Patch Adams.

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7. Jay Roach

While the first two Austin Powers flicks pretty much defined the genre in the latter half of the decade, I don’t think anyone is truly pining to rewatch Mystery, Alaska anytime soon. That release definitely pushes the director down a notch.

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The hit franchise starring Mike Myers gets a good bit of love even today, but Jay Roach never really got much credit for them. In my opinion, though, International Man of Mystery and The Spy Who Shagged Me were groovy enough to warrant Roach a spot on the list.

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6. Harold Ramis

As Harold is one of the more popular names featured here, some of you may be thinking, “What? He made Groundhog Day! He should totally be number one!” Well, I hear you, but despite making one of the highest rated comedies of the decade in Groundhog Day and arguably the most underrated in Analyze This, he also pumped out two of the worst.

Stuart Saves His Family has a 30% on Rotten Tomatoes and Multiplicity a 45%, and both were absolute flops in theaters. It’s a shame—if he only directed those first two, he would have been much higher. Probably number three, or even number two. Oh, well.

R.I.P. legend.

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5. Wes Anderson

Another noteworthy name, Anderson made his directorial debut in 1996 with Bottle Rocket, one of his funniest and more underappreciated works. He followed up two years later with Rushmore, starring Jason Schwarzman and Bill Murray, which launched him into the comedic stratosphere while simultaneously reinvigorating Murray’s career.

Neither film is exactly overt in its humor, but they’re well-made movies that will undoubtedly make you laugh, and despite some weak numbers at the box office, Anderson’s consistent quality impressed filmgoers everywhere.

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4. David O. Russell

Known today for films like The Fighter and Silver Linings Playbook, David O. Russell also released three incredible 90s films that fall wonderfully into the genre at hand: Spanking the Monkey in 1994, Flirting with Disaster in 1996, and Three Kings in 1999.

That last one is the most popular of the trio as it accrued over $100 million bucks in theaters, while all three films culminate in the best average score on Rotten Tomatoes for any director on the list. And with good reason. Flirting with Disaster is perhaps the most glossed-over movie of the era, and it kick-started Ben Stiller’s career as a true leading man. Plus, Three Kings is a must-watch.

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3. The Farrelly Brothers

Of the three movies they directed throughout the decade, Dumb and Dumber is perhaps their worst from a narrative standpoint in spite of its on-paper popularity. That same argument could be made for Kingpin, but either way, both works provide some solid laughs.

There’s Something About Mary is easily their best, and while David O. Russell helped Ben Stiller commence a career in starring roles, this movie evolved both him and Cameron Diaz into household names. And when you combine all three films from the Farrellys, the result is a lot of money at the box office and one of the foremost comedy duos in Hollywood.

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2. Richard Linklater

Coincidentally, his worst-reviewed film of the decade—The Newton Boys, 64% on Rotten Tomatoes—and his best-reviewed—Before Sunrise with a perfect 100% rating—fail to fall into the comedy genre. So, we’ll skip those for now.

SubUrbia in 1996 didn’t rake in theater receipts, nor did it blow critics out of the water, but it’s a good watch, nonetheless. His first two films of the 90s, however, are two of the finest the genre can offer. Kicking things off with the biggest indie film of 1990, Linklater made over a million bucks with Slacker on just a $23 thousand budget, and the picture has since been selected by the Library of Congress for preservation in the National Film Registry.

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That sounds hard to top, but he managed with Dazed and Confused in 1993. You’ll all likely agree that it’s among the finest comedies ever made, and with those two films alone, Linklater’s place amongst the greats has long been cemented in stone—slight pun intended.

Top 10 Comedy Directors of the 90s (10)

1. The Coen Brothers

This was the era in which the brothers made names for themselves as auteurs of the industry by virtue of dark, uniquely-satirical comedy. Although their first two films of the decade—Miller’s Crossing in 1990 and Barton Fink in 1991—weren’t exactly heavy on the laughs, every movie the Coen Brothers helm will feature humor to one degree or another.

The Hudsucker Proxy in 1995 nearly marred their placement with a 59% on Rotten Tomatoes and horrible money at the box office, but the audience gave a great score of 79% and, yeah. It’s really not as bad as the numbers imply.

Their last two films of the decade—Fargo and The Big Lebowski—are now considered comedy classics, have been preserved in the National Film Registry, and are quoted on a daily basis by film fans across the country. They’re two of the most respected comedies ever made, not just of the 90s, and when you throw in three other works with clear-cut comedic qualities, the Coens undoubtedly solidified the number one spot.

Thanks for Reading!

Agree with our list? Who was your favorite comedy director of the 1990s? What was your favorite individual film from them? Let us know in the comments, and again, thanks for reading!

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