Ten Great Underrated Comedy Movies (That you Probably Haven't Seen)

A list of great underrated comedy films was difficult to compile simply because comedy is incredibly broad genre. Many of the films I chose for this list deal with somewhat taboo subject matter. This is often the hallmark of a truly great comedy. Others are films that have fallen through the cracks over the years. What they all have in common is that although nothing dates as badly as comedy, these films have remained as funny through the years as when they were first released. Calling any film a comedy that doesn't go straight for laughs is difficult. A few of these films might be called dramas as well. Of those that are left the term satire might be applied, which is not a term interchangeable with comedy. But each of these movies will make you laugh. Even if some of them will make you feel other things as well.

The Great Dictator (1940)

Charlie Chaplin’s career went into decline once sound films became the norm, like far too many silent stars, but before he was swept into irrelevance, he had one last great film in him. While most Americans still wanted to stay out of the war in Europe, the English born Chaplin was able to get a major Hollywood movie made that attacked Hitler and Mussolini with absurd comic viciousness. Chaplin plays too roles, that of the hapless title dictator of “Tomainia” and a Jewish barber who looked just like the idiotic megalomaniac. Of course they end up trading places. The film greatly upset Hitler upon its release, which was part of Chaplin’s goal, and got Chaplin Oscar nominations for his performance and screenplay but still to this day is not as famous as his silent masterpieces.

The Major and the Minor (1941)

Though he directed nearly every genre you can think of, Billy Wilder is probably best known for his comedies. Still, many people overlook his first film, one of the funniest and most subversive comedies Hollywood ever made. The plot is ridiculous but the dialogue is so sharp and the performances so pitch perfect that it doesn’t matter. Ginger Rogers plays a young woman who can’t afford a full price train ticket home from New York, so she disguises herself as a twelve year old in order to get a child’s fare. She is then forced to continue the ruse when she gets involved with a military school instructor. (Ray Milland.) Any good romantic comedy needs something to keep the couple apart until the end but the fact that Milland thinks Rogers is twelve is probably the most perverse obstacle a major Hollywood movie has ever used. And for fans of Rogers, she dances too.

Miracle of Morgan’s Creek (1944)

Speaking of subversive premises, Preston Sturges may have topped them all with this 1944 masterpiece. Star Betty Hutton goes to a USO show, gets drunk, finds out later that she is pregnant and then tries to get her childhood friend (Eddie Bracken) who has always carried a torch, to marry her. Sturges was under such tight censorship that he couldn’t say the word pregnant but the number of risqué gags he was able to cram into this farce is mind boggling. Sturges later credited the censors for forcing him to be more creative and actually making the film more provocative in the process. Stars Hutton and Bracken are both brilliant but the real scene stealer is probably William Demarest as Hutton’s overprotective father.

Take the Money and Run (1969)

Woody Allen had already made an impression as a stand up, actor and writer, but with this first film as director he established himself as one of the most inventive comedic directors of his generation. The film follows a loose “mockumentary” style, where Allen plays a hapless criminal and we see the development of his life of crime. As Allen developed as a director he began to mix his gags with political and social satire but you’ll find none of that here. He just wants to get laughs and the result is one of the most consistently funny films Allen has made.

The Landlord (1970)

Hal Ashby remains one of the most underrated directors of the 70s partially because of the sharp decline of his work in the 80s and because of his early death. His first film remains his least well known work. Beau Bridges plays a spoiled rich kid who buys an all-black tenement building planning to fix it up and turn the current residents out. As he spends more time with them, he finds that his horizons are broadened and he learns much more than he ever thought he would from the venture. Ashby’s film is one of the most insightful and brave examinations of race ever made and a darkly funny satire that makes sharp criticisms of American racial politics.

Paper Moon (1973)

Tough Tatum O’Neil won the best supporting actress Oscar, becoming the youngest winner ever; far too many people have not seen Peter Bogdanovitch’s brilliant comedy. Con artist Ryan O’Neil gets stuck with a little girl (his real life daughter) and teaches her the ropes of his trade. Bogdanovitch was influenced by early Hollywood screwball comedy and the film is a loving tribute to that style. Madelyn Kahn was also nominated for an Oscar for her role as Trixie Delight but lost to Tatum, ironic since the two characters were essentially rivals in the film as well.

Penn and Teller Get Killed (1989)

Director Arthur Penn (Bonnie and Clyde) helmed this comedy written by and starring magicians / comedians / activists Penn and Teller. The film is a lot like Penn and Teller’s act. It is funny, dark, weird and full of quirky misdirection. Despite not being a mainstream hit it has gained a pretty passionate cult following over the years. Anybody who wants to see something off the beaten path and a little twisted need look no further. The ending alone has to be both one of the funniest and most disturbing scenes in movie history.

Ed Wood (1994)

Director Tim Burton is highly praised for his campy effects driven movies but even some of his biggest fans skipped one of his best films. Johnny Depp plays Edward D. Wood Jr., the worst filmmaker of all time, who remains enthusiastic despite constant failure. Depp has never been better and Martin Landau won an Oscar for playing Wood’s favorite star Bela Lugosi. The rest of the supporting cast, including Sarah Jessica Parker, Bill Murray and Jeffrey Jones is also excellent and Burton gives the finest, most subtle and most nuanced direction of his career. After this little gem failed at the box office, Burton seemed even more determined to make blockbusters, which is a real shame.

Wet Hot American Summer (2001)

Comedians David Wain and Michael Showalter created this satire of 80s teen comedies. (Which Wain directed and Showalter starred in.) The film puzzled audiences and critics with its decidedly postmodern style but has gained such a passionate cult following over the years that now there is talk of a sequel. The cast includes an eclectic mix of comedic actors including David Hyde Pierce, Janeane Garofalo, Paul Rudd, Amy Poehler, Christopher Meloni and many then obscure but now famous actors. Since the point of the film is to skewer movies that were themselves comedies, the humor is often of the “meta-joke” or cerebral variety but there are few films in the past twenty years that have been so funny from beginning to end.

Pumpkin (2004)

The fact that Pumpkin so horrified critics and confused audiences should be no surprise based on the subject matter. Christina Ricci (who also produced) plays a spoiled sorority girl who finds herself falling in love with a mentally challenged boy. The film’s humor is so dark and politically incorrect that it is still a wonder to me that it got made at all. Many people are so put off by the jarring tone shifts that they miss the film’s complexity. The film viciously satirizes the way society treats the handicapped but then also viciously satirizes well intentioned liberal ideas of how the handicapped should be viewed. The filmmakers structure this around a plot and style that mimics melodramas and social problem films of the 50s and 60s as well as the kind of movie might be playing on the Lifetime network. The result is one of the most unique and cringe inducing comedies of the past decade.