Risky & Risque: Top 10 Comedies That Take A Chance & Win

Dan Grant looks at ten exceptional comedies that take risks in their pursuit of a unique comedic vision and succeed. The courage of these filmmakers has given audiences some of the greatest films ever made.

There are hundreds of funny films. Maybe thousands. There’s nothing like discovering that film that catches you off guard and makes you laugh when you are least expecting it. And then there’s films that basically take a risk. Or in this case, a lot of risk. Some of these films were from directors who had nothing to lose and some of them were just artists making things up as they went along. But what they all have in common is that they all took risks and those risks paid off to make these more than just comedies. It made them legendary comedies.

Here are the top ten comedies that pulled no punches and just went for it:

10. This is the End (2013)

Great Horror Movie Jerks - Top 10 FilmsIf I was to write this same article ten years from now, this might make the number one slot but seeing as it is two years old, it needs time to marinate a little and get appreciated. They say there are six or seven stories that you can tell in Hollywood. Every film is just a different version of those stories. I think this one makes it 8. In it, you have actors playing themselves and in the process, they insult, belittle, antagonize and berate one another to the point of hilarity. There is one scene in the film that will go on to become as iconic as any other scene in any comedy. And that is when Danny McBride and James Franco are discussing why McBride decided to use Franco’s porn magazine as masturbation material. It’s so over the top funny that it cannot be described. Seth Rogen directed all of his friends and because he is well connected, he got them to do and say things that perhaps no other director, not even the likes of Judd Apatow, could get them to do and say. Also, check out Michael Cera’s version of himself. This, in my opinion, is as funny as they come.

9. Clerks (1994)

Clerks - Top 10 FilmsBy now you might have heard the story of how Kevin Smith used up all of his credit cards and borrowed money from friends to make this $27,000 black and white movie about store clerks who really don’t like you. What makes this film so audacious is the language Smith uses. While he seems to go over the top at times, he also accurately tells jokes about youth and he has some terrific film observation. There’s a scene discussing the politics of blowing up the Death Star in Jedi that is both funny and very interesting. But what makes this film belong on the list are scenes like screwing a dead guy in the bathroom, snowballing and of course Silent Bob’s ten seconds of dialogue.

8. Porky’s (1982)

Porky's - Top 10 FilmsBob Clark wrote and directed the ultimate sex comedy. Here’s a film famous for its nudity but almost as famous is the genius of the script. This is a film that took an enormous amount of risks. The T&A movies were in full swing at this point but none of them did what Porky’s does. There’s a shower scene which includes Pauly the Penis, there’s Lassie and then one of the most brash and crazy scenes you will find in any film is the principals office when they discuss using a sketch artist to describe a boy’s penis with a mole on it. You can easily find this scene on youtube and if you watch it, notice how the entire 4 minute scene is done without any cuts. And if you are not laughing by the end of it, well, I guess we just have different senses of humour.

7. Anchorman (2004)

Anchorman - Top 10 FilmsI don’t think this had a real script. I think they just had ideas, and then told Will Ferrell and friends to wing it. When you have Ferrell, Paul Rudd and Steve Carell plus cameos by Vince Vaughn and Ben Stiller, you are in for a treat. There are a litany of scenes that are kind of legendary but the one that stands out is the rumble. In the middle of a comedy about a San Diego news team, you have a rumble that takes place for absolutely no reason. It ends with Brick, played by Carell, killing a man with a trident, to which Ron Burgundy responds later, “Yes Brick, I’ve been meaning to tell you that you should find a safe house, lay low for a while because you are probably wanted for murder.” Anchorman takes some getting used to but it is worth multiple viewings.

6. American Pie (1999)

American Pie - Top 10 FilmsAt this point in Hollywood, the teen film was dead. Long gone was the brilliance of films like Fast Times and Ridgemont High, The Sure Thing and the various films of John Hughes. What we were left with was unfunny ersatz garbage hoping to make a quick buck. Then wonder kids Adam Hertz and Paul Weitz came along and gave us American Pie. Sure, it knew how kids spoke to one another and it also had some funny and astute observations about relationships but what put it over the top was two things. One was Stifler and the other was Michelle and her flute. Her “this one time at band camp” scene probably caused a lot of spit up drinks in the movie theater. It was simply a scene that no one saw coming. It was brilliantly written and turned American Pie from a funny film into one that was ballsy and a little X rated.

5. South Park: Bigger Longer and Uncut (1999)

South Park - Top 10 FilmsThere has never been a film like this one and there probably never will be again. The use of the F-word has never been more prevalent nor funny. If you have not seen this film, nothing I do to tell you about it will do it justice. Just find it and watch it with no one around.

4. Animal House (1978)

Animal House - Top 10 FilmsThe Godfather had the head of a horse in a bed. Animal House had something to do with hotdogs and horses. Animal House might have been the first film to start the frat house house, college film craze. It’s a very funny film with a very nice cast but what puts it over the top is John Belushi. “Over? Did you say over? Was it over when the German’s bombed Pearl Harbor?” And so on. Animal House could have fallen flat on its face but instead it became of the greatest comedies of all time because it took a few risks.

3. A Fish Called Wanda (1988)

A Fish Called Wanda, John Cleese, Michael Palin, Jamie Lee Curtis, British-American Comedy - Top 10 FilmsA film that combine the best of British comedy with American comedy. Starring comedy giants from the Monty Python Gang, and two actors not known for comedy, this film pushed all the right buttons and in the process became one of the all time greats. Similar to This is the End, John Cleese and Charles Chrichton wrote a biting satire about British life and how stuffy and proper it can be at times living in England. This allowed the brash and ill mannered American cretin, played by the brilliant Kevin Kline, to just cut loose and dig into every possible stereotype of English life. And if that wasn’t enough, Kline being the ignorant and stupid American, also gets his due ridicule by the cast. It was a big risk that paid off handsomely.

2. Beverly Hills Cop (1984)

Axel Foley, Eddie Murphy, Beverly Hills Cop, 1980s Comedy Film Characters - Top 10 FilmsEddie Murphy changed comedy, at least American comedy. Perhaps there was a lot of improvisation in British comedy but up until Murphy started making movies, scripts were mostly adhered to. Then Eddie came in and changed everything. The original Beverly Hills Cop script that made its way around Hollywood, was basically a very by the numbers cop movie and it originally had Sylvester Stallone slated to star in it. He eventually turned it down feeling that it wasn’t quite right for him at the time. Then when Murphy came on board it was rewritten to be more of a comedy. What no one could foresee was the comedic genius of Murphy and how he turned regular straight laced scenes into legendary comedy sets. The “limon twist” scene with Bronson Pinchot, the “not gonna fall for the banana in the tail pipe scene” the “IRS porsche scene,” and many, many others were all improvised by Murphy. Soon, comedies were letting their actors improvise a little more. Murphy is a pioneer in this sense.

1. Monty Python and the Holy Grail (1975)

Monty Python and the Holy Grail, Film, gilliam,Is there a plot to this film? I guess so. But does it really matter? Not really. The Monty Python group began in 1969 when their sketch comedy Monty Python and the Flying Circus appeared on the BBC. From there, their influence on comedy is unmatched. With a budget of about 250,000 pounds, this comedy went on to gross hundreds of millions of dollars world wide over the years. With famous scenes like the knight who keeps losing limbs, to the trivia where the trivia master is out smarted to the men acting like they are riding horses and everything else, everything in this film is bombastic and far beyond the norm. This is perhaps the ballsiest and riskiest comedy ever made and it easily makes the number one slot of comedies that just go for it all.

Written and Compiled by Dan Grant

About the Author
Dan Grant is an author and horror film fan from Canada. His first novel Terrified and Defenseless is now available for e-download from Amazon. Follow Dan on Twitter @baumer72.

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  1. Avatar
    Rory Fish Reply

    Some classics right here, Dan. I don’t think anyone can argue about the risks the Monty Python team took so that’s a great number one. I’m wondering if you can make a case for Team America instead of South Park since they had already broke new ground on TV with that show, creating something more unique with Team America. That said, I love most of the films on this list, especially Beverly Hills Cop, A Fish Called Wanda and Clerks.

  2. Avatar
    Callum Reply

    Great top 10 Dan!

    Holy Grail is my fave Python film but it’s great to see John Cleese make the list twice with A Fish Called Wanda. He was a king risk taker!

    Good spot with Beverly Hills Cop – so glad Stallone walked away from the project.

  3. Avatar
    Dan Grant Reply

    Thanks for the thoughts. Glad to see so much love for Beverly Hills Cop.

    Theres a lot of other films that could have made the list as well.

    • Avatar
      Callum Reply

      Beverly Hills Cop is probably my most watched 80s movie! Love it!

  4. Avatar
    Killinger Reply

    How about Dr.Strangelove?

  5. Avatar
    ArchE Reply

    Oh, I like it, I like it A-Lot!

    Great topic. It’s got me thinking… Which is a good thing since my thinking cap is getting a bit dusty.

    Let me think…

    Oh… Woody Allen… Sleepers.

    Now then… Kentucky Fried Movie.

    Things are flowing now.

    Oh. Er. Brain freeze. Perhaps Airplane would be a good one as it ushered in a period of balls-out slapstick. An American Werewolf In London for combining comedy and horror and making it work seamlessly. Is there room for Mel Brooks and his incredible Blazing Saddles – baked beans-eating cowboys with a case of the farts and an African-American Sheriff in Red Neck City are both risky and risqué.

  6. Avatar
    Neal Damiano Reply

    Glad to see Clerks included in your list, Dan
    Well deserved spot , Smith took a shot in the dark chance with making a film on a shoe string budget and a risk of producing a movie that makes him and his friends laugh on his own terms.
    The film ended up winning at Sundance.

  7. Avatar
    Dan Grant Reply

    Airplane was on my list of 15. Ultimately i couldn’t find a place for it in the top ten. But it was definitely a risky film that obviously paid off beautifully.

  8. Avatar
    Hanky Reply

    Loved Anchorman and This Is The End. And I think most of Kevin Smith’s could be on this list. Not going to argue with Clerks being their but Mallrats, Chasing Amy and Dogma were all very risky films.

  9. Avatar
    Dan Grant Reply

    Hanky: I agree with you about Smith’s movies. I think Dogma and Chasing Amy are terrific films, Chasing amy in particular. But I could really only include one of his films in a list of ten so I chose his first one.

    Another one I thought about was Zoolander. Sure there have been movies about dumb people before but Zoolander just did a lot of over the top things. But again, only room for ten.

  10. Avatar
    Hanky Reply

    Totally agree with Clerks being the one to include here. Maxing out all those credits cards was sure taking a risk. I’m just glad it worked out for him because Clerks is one of the best slacker-coms to come out of the 90s. I like the fact Smith continues to try to take risks with his work. It doesn’t always pay off but when it does it’s great.

  11. Avatar
    Lee Burns Reply

    Super Troopers would make a good addition to this list.

    • Avatar
      Dan Reply

      I was thinking the same actually. Shame the Broken Lizard team haven’t done anything half as good since.

  12. Avatar
    Dan Grant Reply

    Smiths Red State was totally self financed and although it is not a comedy and it is about as diametric a film as you will find in Smiths repertoire is also pretty brilliant in my opinion. Not sure if you have seen that one Hanky, but if you have not you should try to go out and find it. John Goodman is pretty intense in that film.

    • Avatar
      Callum Reply

      Red State was very different, not sure I enjoyed it but I must see it again.

  13. Avatar
    Hanky Reply

    I have seen Red State. It was mental. Very different to Smith films before it.

  14. Avatar
    Dan Grant Reply

    Super Troopers was another really good one. I kind of forgot about it when doing this list. But it definitely took some risks. There’s Something About Mary almost made the list as well as it has to be the Farrelly’s best film and when you can have a scene where post masturbation residue is used as hair gel, you have done your job.

    • Avatar
      Dan Reply

      I think that scene in “Mary” you mention is a great encapsulation of what you’re talking about in this top 10! 🙂

  15. Avatar
    Sonj Reply

    Love your list!!!
    I quote a lot from “office space”
    Not sure if that’s fits
    I know how much you love Beverly Hills cop!! Haha

  16. Avatar
    Alfred Reply

    There’s Something About Mary is probably funnier then half of the film in the top 10, but based on the criteria that Dan set it wouldn’t bit, it was a good comedy, but not much of a risky or ballsy project than the listed ones. Nice to see the appreciation for British comedy gold, nicely put article altogether.

  17. Avatar
    Jackson Reply

    When the Farrelly bros. go for it and it works they do make some good comedies. When they don’t work, however, you get some real bad ones. That said, I think Kingpin or Dumb and Dumber would make nice additions to this list but not sure who you’d get rid of. Great to see the mention of Beverly Hills Cop and Eddie Murphy’s contribution to comedy.

  18. Avatar
    Dan Reply

    I agree with the others that this is a terrific idea for a top 10, Dan. Comedy can become so stale, especially when studios are trying to make a cash-cow that will work at the box office as a piece of mainstream entertainment but importantly not offend anyone and thus turn-off the masses. The ballsiest filmmakers always aim for something a bit different.

    I’m not a huge fan of either South Park or Team America but Trey Parker and Matt Stone have definitely pushed the boat out in more recent time and created comedy that, like you say, “just goes for it” without concerning itself with the potential backlash.

    Kubrick Dr. Strangelove is a good one. The film dares to satirize elements of political society others wouldn’t dare go near.

    I love your top 4 choices though. All personal favorites of mine.

  19. Avatar
    Dan Grant Reply

    @ Sonj: Thanks for commenting Sonj. Miss ya. As for Office Space, it came very close to making the list, in fact, it could have made the list. That film did everything right and took a lot of risks. Lumberg is one of the funniest characters of the last 20 years imo.

    @Alfred….thanks for taking the time to read and comment. The hair gel scene is very funny and so are about a dozen other risky scenes.

    @Dan: I really need to see Dr. Strangelove again. As for Parker and Stone, I’m not their biggest fan either but they definitely take a lot of risks and some work, some dont….South Park did. Thanks for such a great format with this article. You know I struggled with the title, but you nailed it.

    @Jackson: The Farrelly’s are hit and miss, I agree. Me Myself and Irene also could have made the list based simply on the strength of Anthony Anderson and the other two black actors that played Jim Carrey’s sons. There were some scenes that had me choking with laughter.

  20. Avatar
    Lindo Reply

    Brill top 10 Dan. All these movies are so funny but risky all the same. I remember hearing about stallone doing Beverly Hills Cop, what a difference that would have made. Eddie Murphy took it to another level.

  21. Avatar
    Dan Grant Reply

    Hey Lindo: If you believe Stallone, he is the one who actually recommended Murphy take it over. He told Arsenio Hall this back in the late 80’s or early 90’s on his show. This is a bit off topic but I think Stallone is one of the smartest men in the industry and if this story is true, not only did he make a wise decision, but he catapulted Murphy into another stratosphere.

  22. Avatar
    Silas Reply

    Good piece. I liked how you covered a range of eras as well. A lot of “top” lists end up being heavily skewed towards a particular era, recent films, ’50s, whatever the person likes. Nice to see stuff from 2 years ago as well as 40 years ago.

  23. Avatar
    Dan Reply

    Thanks Silas. I truly believe TITE will become a classic one day. The scene that I talked about in that movie had me doubling over in laughter and that is not an exaggeration. I had never seen something like that discussed in movies before it was incredibly well written and so brilliantly performed by Danny McBride and James Franco.

  24. Avatar
    Evan Crean Reply

    This is the End definitely takes a lot of risks, but it’s too self-aware and self-indulgent for me. It feels more like Rogen directing his friends while they try crazy stuff that doesn’t work than people setting out to tell a coherent story. I do agree with many of the other films on your list though, like Clerks, Anchorman, American Pie, South Park, Animal House, Beverly Hills Cop, and Holy Grail. I knew about the Stallone/Cobra thing, but didn’t realize how much of Beverly Hills Cop was improvised. Amazed it works so well. I’m actually ashamed to say I’ve never seen A Fish Called Wanda. I should probably get on that.

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