10 Great Comedy Movies You’ve Probably Never Seen

6. Bamboozled (Spike Lee, 2000)

Bamboozled (2000)

As promised in the section about Boudu Saved From Drowning, it’s time to talk about Spike Lee! One of his most overlooked films, too. Bamboozled, released in 2000, was quite the film to put Spike into the 21st century, focusing on a TV producer named Pi’erre Delacroix who, when annoyed by his ideas being consistently turned down, pitches the worst idea he can think of (that idea being a 21st century minstrel show…) only for the company to accept it, and the show to go on to become a massive hit.

Coming from someone as wonderfully aggressive as Spike Lee, the film is just as funny as it is achingly frustrating and upsetting, culminating in a montage so mind blowing that it might just be the greatest thing Spike ever did alongside the rapid-fire racial slur scene in Do The Right Thing.

Bamboozled is one of the most ridiculously overlooked, scathing but also hilarious looks at modern racism and a film that deserves so much more credit than it received upon release. Somehow, almost twenty years after it came out, it’s still struggling to find an audience. It’s an absolute must for any fan of Lee.


7. The Heartbreak Kid (The Farrelly Brothers, 2007)

Okay, this one may have some of you scratching your heads and wondering how you’ve ended up reading a list where Spike Lee sits next to the Farrelly Brothers. Admittedly, it’s a fine response to have, and one that many will share, however, if you’re one of the many who happen to enjoy relaxing with sillier gross-out comedies – especially when the characters are just as disgusting as many of the jokes – this is one you’re almost guaranteed to enjoy.

The pacing is incredibly quick, the jokes are relentless and Ben Stiller gives one of the best recent comic performances as one of the most hateful characters in 21st century film… he is truly despicable in a way that so few other characters are.

It may not have too much by way of style, but the script and the performances are both enthralling enough to make it a blast, and the desperation on the part of the Farrelly Brothers to keep their audience disgusted really shows, making this absolutely vile character study about one of cinema’s most hateful.

It’s absolutely fascinating, even if you end up hating it, just seeing how low the Farrelly Brothers go in looking for their laughs. It’s confusing, hilarious, baffling and disgusting, and it’s one of the most interesting comedies to come out this century.


8. Living in Oblivion (Tom DiCillo, 1995)

Living In Oblivion

Living in Oblivion, a film told in three chapters and starring Steve Buscemi, is another brilliantly infuriating comedy. Buscemi plays Nick, a young director working on a low budget independent film, and the film tells the story of three different times on the set and how they all go horrendously wrong in one way or another, whether it’s due to a lack of communication, a crazy actress or an egotistical maniac for a star.

The pacing is incredibly quick, and though the majority of the jokes do come out of seeing the frustration on the set and in the performances (as well as in the achingly awkward feeling that accompanies the majority of the film), it’s still just incredibly funny.

For any aspiring filmmaker, it also acts as a rulebook of things to do and things not to do when on set, presenting many of the challenges that come with trying to direct a first feature on a low budget – in fact, when looking at the film through the lens of a filmmaker, it’s just as terrifying and relatable as it is funny and frustrating. It’s a wonderful film, with Buscemi giving one of his finest performances to date. Not one to be missed, even if it is quite difficult to find.


9. Cecil B. Demented (John Waters, 2000)

John Waters, more than likely bringing to mind the notorious Pink Flamingos (among other insane efforts), isn’t mentioned so much now, however, some seem quite content in thinking that he only made films during the 1970s and neglect his later work – which means they’re missing out on one of his very best films in Cecil B. Demented.

The film focuses on a group of deranged movie buffs, including a Fassbinder fan and Cecil B himself, trying to make an underground movie and even kidnapping their star. The film is just as chaotic as you’d expect from John Waters, with incredibly fast pacing, consistently extreme and bizarre dark humour focused on a wonderful gang of oddball misfits, and it’s just wonderful.

It’s somehow the most brilliant mix of the weirder early work of Waters and the… slightly more commercial and easygoing work he had in the 80s with his musicals to the point that it works as both a very relaxed comedy and also a really gross and disturbing film if you step back and really think about what you’re witnessing.

It’s incredibly fun, the performances are fantastic – especially from Stephen Dorff (who never seems to really get the credit he deserves), the pacing is whip smart and there are just so many wonderful film references – it’s too much fun to be ignored… and hey, you could even double bill it with Living In Oblivion!


10. The Show About The Show (Caveh Zahedi, 2017)

Ending on probably the least known of all of the films features on this list, Zahedi’s The Show About The Show is a mesmerisingly unique and creative dark comedy focusing on the behind the scenes of Caveh Zahedi’s new show.

Edited together and made into a feature length film, The Show About The Show is just so fascinating. Seeing Zahedi be as open as he is with the audience about his feelings for people (specifically at a few incredibly tender points where he speaks to the camera about things he hasn’t even said to the people they involve, using the camera as some kind of diary) creates this brilliant dynamic where he is really quite sympathetic and innocent, which makes his actions throughout all the more emotionally investing to the audience, and therefore, almost any emotional beat hits twice as hard. It’s hilarious, it’s hard hitting and it’s just beautiful, as hard as it is to find.