What Are the Best Movie Comedies of All Time?

Today: The Flying Monkey answers all your questions, including what classic movie comedies he thinks everyone should see!

Have an entertainment-related question? Contact me here (and be sure and include your city and state and/or country!)

Q: By random chance, I found the movie Some Like It Hot at the library, and after seeing the two guys in drag and Marilyn Monroe on the cover, I decided that it was going to be awesome and checked it out immediately. I was right: this movie should be required watching for all young gay men out there! I am not familiar with many black and white classics, and perhaps that's why I love it that much more. It's not only hysterical, but also one of the most quotable films that I have seen to date, plus it ends with a gay joke! To think, a black and white movie from my conservative grandparents’ era ending with a funny gay joke like that.

I went back and checked AfterElton's Top 50 Gay Films again, posted last September, and found that the oldest films are The Boys in the Band (1970) and The Rocky Horror Picture Show (1975). To my surprise and dismay, Some Like It Hot is not there, and it totally should be!

What other older films would the Flying Monkey consider to be required watching? I mean the black and white era, there must be more examples of films from that time period where they take such big risks to reference "the gay" in one way or another. -- Daniel, Vacaville, CA

A: I agree Some Like It Hot is wonderful (and so does the American Film Institute, which voted it the best movie comedy of all time), but I’m not sure it really qualifies as “gay.” Except for that final joke, it mostly bends over backward not to be gay – which makes sense since movies were effectively all censored by something called the Hays Code, which was in place from 1934 until a slow fade-out in the 1960s, making it virtually impossible to release any film with explicit gay content, especially if it was positive.

Still, here are my picks for the classic comedies (mostly black-and-white, but a few in color) that I think everyone should see – but that just might have a particular appeal to gay and bi boys and our supporters.

Working backward, I’d start with Monty Python and the Holy Grail (1975), which stars the late gay Python, Graham Chapman, as the film’s “straight” man, King Arthur – and he’s just about the funniest straight man of all time. Incidentally, Monty Python basically created the modern ironic comedy sensibility, and this is when they first broke through to American audiences.

Barbra Streisand has never seemed that high on What’s Up Doc (1972), but in my opinion it’s far and away her second-best film (after Funny Girl). It’s Streisand at her most appealing, and it frustrates me that she was so determined to be a “serious” actress when it’s obvious in retrospect she’s a much better (and much more subtle) film comedian. But even without her, it’s a great film – even better than the classic screwball comedies to which it pays homage.

If you’re gay, you need to be fully versed in the comic wonder that is Madeline Kahn, who stole both Young Frankenstein (1974) and Paper Moon (1971) from their respective stars. Sadly, despite these early successes (and also What’s Up Doc, which introduced her), Kahn didn’t go on to the movie career she deserved.

Barbra Streisand and Ryan O'Neal in What's Up Doc?

Harold & Maude (1971) may be my single favorite movie of all time – I still can’t believe it got produced! – but I’m telling you in advance that it’s not for all tastes. Still, if you’re gay or bi and you don’t love Ruth Gordon in this film, there’s something seriously wrong with you.

In 1950, Bette Davis didn’t win the Oscar for All About Eve and Gloria Swanson didn’t win for Sunset Boulevard – two of the greatest, most iconic film performances of all time. They lost to Judy Holliday in Born Yesterday. But you know what? Oscar voters may have been right: Holliday is absolutely fantastic as the hands-down best dumb blond in Hollywood history (despite the fact that in real life the actress had an IQ of 172!). I was determined to hate this movie for stealing the third Oscar Bette Davis so deserved (and never got), but I ended up loving it instead.

William Holden and Judy Holliday in Born Yesterday

I could never say enough about Billy Wilder (the director of Some Like it Hot, and also Sunset Boulevard), but you should absolutely check out Sabrina (1954), the best romantic comedy of all time (and Audrey Hepburn’s best movie) and The Apartment (1960), which stars two of filmdom’s best screen comedians, Shirley MacLaine and Jack Lemmon, at the absolute peak of their abilities. Despite being released in the middle of the Hays Code, The Apartment is also surprisingly racy -- but I’ll be damned if you can point to a single line that makes it feel that way.

With four Oscars, most people think of Katherine Hepburn as a dramatic actress – and that’s certainly where she excelled in later years. But she was also one of Hollywood’s best comedians, and many of her early comedies are now classics. Personally, I find Bringing Up Baby (1938) and The Philadelphia Story (1940) to be dated, so I’d recommend Woman of the Year (1942) – a gender-sparring comedy which has the added bonus of giving you a taste of Hepburn’s famous screen partnership with her real-life lover Spencer Tracy.

Tracy and Hepburn in Woman of the Year

What have I missed? Oh, only about a hundred movies. But I have to shut up sometime!

Have an entertainment-related question? Contact me here (and be sure and include your city and state and/or country!)