They say it’s easier to make audiences cry than to make them laugh, and this idea is supported by the number of great directors who have tried and failed to make comedies. While many of these filmmakers have earned Oscars for their directorial output, they just couldn’t get things right when trying to be funny.

Some of the greatest directors have stumbled in the realm of comedy, as icons like Steven Spielberg and Francis Ford Coppola struggled to get a laugh from viewers. Whether it was genre-bending comedies that couldn’t get their tone right or films whose scripts weren’t up to scratch, all of these films mark low points in their respective filmmakers’ careers.

To be a great filmmaker doesn’t mean being a master of every genre, but these cinematic failures do show a willingness to explore new territory. Although they may not have gained critical acclaim, the fact these filmmakers took a risk in a genre that didn’t suit them makes the work where they got things right all the more impressive.

6

Brian De Palma

Wise Guys (1986)

Despite making one of the greatest gangster movies of all time with Scarface three years before, Brian De Palma made perhaps his worst movie when he tried to show off the funny side of mobsters in Wise Guys. Despite an impressive cast including Danny DeVito, Joe Piscopo, and Harvey Keitel, the results were dull and humorless.

Wise Guys played out more like an unproduced sitcom pilot than a star-studded comedy from one of the era’s greatest directors. As a film filled with meandering chase scenes and gags that don’t land, De Palma (via Business Insider) himself said it was “a movie I wish I hadn’t done.”

5

Roman Polanski

Pirates (1986)

It’s hard to imagine the same director who made Rosemary’s Baby, Chinatown, and The Pianist was also behind Pirates, but it’s true. As a swashbuckling adventure inspired by Roman Polanski’s childhood love of classic pirate films, everything about this film fell flat on its feet, and not even comedy star Walter Matthau could save it.

As a majorly disappointing release, the behind-the-scenes controversy surrounding Pirates was even more upsetting. As a controversial figure, Polanski has several charges of Sєxual ᴀssault against him, and in 2010, Pirates actress Charlotte Lewis came forward with more accusations of ᴀssault against the director (via ABC.) While Pirates was marketed as a comedy, there’s nothing funny about its horrid legacy.

4

Ron Howard

The Dilemma (2011)

Ron Howard is a director who proved himself capable across many genres, with Best Picture winners like A Beautiful Mind and historical dramas such as Apollo 13 standing out. However, his career has also had several misfires, like the divisive Star Wars spin-off Solo and the hugely underwhelming comedy-drama The Dilemma.

As a strange film that’s never quite sure if it wants to be comedic or serious, The Dilemma told the story of a businessman struggling to tell his friend he witnessed his wife kissing another man without ruining their crucial upcoming presentation. As The Dilemma jumps between intense psychological drama and slapstick comedy, it’s clear Howard never got the balance right.

3

William Friedkin

Deal of the Century (1983)

As the director of classics like The French Connection and The Exorcist, the Academy Award-winning filmmaker William Friedkin has proved his talents across action, crime, horror, and neo-noir. Yet, it was Friedkin’s 1980s Chevy Chase comedy Deal of the Century that marked a low point in his career and now stands at an abysmal 10% on Rotten Tomatoes.

With Chase as an arms dealer attempting to sell weapons to a South American dictator, Deal of the Century was a disappointing collection of lazy stereotypes that lacked the satirical bite needed to make a story like this work. As a disappointing release that failed to get the best from either Friedkin or Chase, Deal of the Century was best forgotten about entirely.

2

Steven Spielberg

1941 (1979)

The name Steven Spielberg is synonymous with great movies, and in the 1970s this director proved himself one of the most exciting up-and-coming names around. From his breakout success with Jaws to the artistic integrity of Close Encounters of the Third Kind, at one point, it felt like Spielberg could do no wrong.

However, this excitement came to a screeching halt with 1941, a World War II comedy that just wasn’t funny. With major comedy stars like Dan Aykroyd, John Belushi, and John Candy among its cast, on paper, 1941 looked like a recipe for success, but in practice it was a frantic mess that was packed with jokes that never seemed to land.

While Spielberg’s incredible talents are on display throughout, and the film looks absolutely fantastic, this was not enough to save 1941 from mediocrity. Spielberg can get comedy right when it’s paired with other genres, like action in Indiana Jones or crime in Catch Me If You Can, but when he tries to be funny, like in 1941, it just doesn’t work.

1

Francis Ford Coppola

Jack (1996)

It’s truly hard to make peace with the fact that the same director who made The Godfather and Apocalypse Now was also responsible for the cinematic abomination that was Jack. With Robin Williams as a boy with a medical condition that makes him age four times faster than normal, the juvenile humor of Jack was truly bottom-of-the-barrel stuff.

As a nominee for Worst Picture at the 1996 Stinkers Bad Movie Awards, Jack just couldn’t strike the right balance between its strange narrative and unnerving performance from Williams. Although Williams is clearly a comedy master, this material just wasn’t right for him, and it’s hard to imagine anyone making this movie work as intended.

Coppola has had plenty of missteps in his long and varied career, with his most recent release, Megalopolis, being yet another big swing for the fences. However, Jack can’t even be admired as an artist trying and failing, as it was presented as a broad comedy only for audiences to be confronted with something that was totally unwatchable.

Sources: Business Insider, Rotten Tomatoes