As movie-goers, we are all familiar with that excruciating moment when you are watching a movie and the action is so horribly uncomfortable that you actually feel the need to cover your own face. It’s this nonsensically powerful moment when you actually feel embarrassed for a fictional character because of some terribly awkward scenario that you’d rather watch a murder than bare witness to. It’s like a horror movie almost – it’s that same turtle reaction where you just want to shrink away. And like horror, it’s either done really well or it’s abused, which is why I want to share with you the films I think did it the very best.

Oh, and if you are wondering why I only picked 9 – it’s the most awkward number I could think of.

9. Wedding Crashers

It’s naturally going to be awkward when you are following two characters whose hobby is to attend weddings of complete strangers under false identities in order to pick up women. As brilliant this idea may be, watching our main characters mingle with the guests and family, we can’t help but know that – much watching like a drunk lion tamer – it’s only going to be a matter of time before things go horribly wrong. The film does an amazing job at making this happen in the least expected way, as the main characters get sucked into a post-wedding get together with the bride’s upper class family lead by an all powerful U.S. Secretary of the Treasury and highly suspicious father of the bride played by Christopher Walken.

This is our catalyst for the awkwardness, as all actions must be made carefully to prevent this one frightening man from knowing the truth. Things couldn’t be worse, as one of or heroes played by Vince Vaughn spends this outing subjected to the Secretary’s ultra-insane, danger-slut daughter who goes great lengths of making every waking second a horror story of awkwardness – especially during a certain dinner scene. Combine this with a racist grandmother, a sexually confused gothic artist son, and of course the Secretary’s wife – who is looking to jump the first young man unfortunate enough to be alone in a room with her.

8. There’s Something About Mary

I want everyone to know right now that this is going to be the only Ben Stiller movie I include. The reason why is that I think that, besides this film, awkward Ben Stiller films are to comedy what the Paranormal Activity series are to horror: cheap. Mind you – I love those Paranormal Activity films – and they work, just like most of those Ben Stiller movies work at being awkward, but it’s an easy awkwardness – a cheap get.

There’s Something About Mary could very easily been lost in that pile of movies had it not been done so early in Stiller’s film career. And perhaps it wouldn’t be on this list if I didn’t have such an untainted fondness of the very pure discomfort and awkwardness that surrounds Stiller’s character. He literally goes from one horrible situation to the next – all starting with one of the most painful scenes involving genitals and a zipper. Weirdly enough, I think the best moment of awkwardness in the whole film is when his friend, played by Chris Elliot, jokingly tells him that he is dying. It’s brief and yet really speaks to the character’s inability to even respond correctly in such a basic situation.

7. Being There

This is the second to last time Peter Sellers (think Dr. Strangelove) acted in a motion picture before his death, and it’s personally the film I recall him most fondly in. The story follows a gardener named Chance – or has he puts it, Chance the gardener – who has spent his whole life working under the supervision of one wealthy man. Being rather simple-minded, Chance knows only what he has learned from watching television and from his work as a gardener. Once his employer dies, Chance is forced to go out in the world for the first time – the world, in this case, being the city of Washington D.C.

Here’s the fun part – basically the entire film is based around one simple fact: if you’re old, white, and wearing a suit then people will assume you are important. This is what happens as Chance the gardener gets entangled in the life of a high-ranking political advisor and becomes, though a miscommunication, known as “Chauncey Gardiner.” What follows is a wonderful story of a very simple human being having every minimal thought that comes out of his mouth be misinterpreted for symbolic brilliance as the character moves higher and higher up the ranks of importance, eventually working as an advisor to the President of the United States.

What makes it all so awkward is that, as the audience, you know that when this guy is talking about gardening he isn’t using it as a metaphor but actually, you know, talking about gardening. Watching every conversation is like getting teeth pulled as you wait for everyone else to finally catch on to what’s going on. The humor, of course, is that they never really do. All of this comes to its peak when you watch what is probably the most awkward sex scene you’ll ever see in a film.

6. The 40 Year Old Virgin

Yeah, no surprise here. The painfulness starts the moment Steve Carell’s virgin character Andy is forced into an over-poker conversation with the guys he works with about sex, and only gets worse from there as he fumbles through a clearly misinformed description of the female (as opposed to male) boob. Once outed, his whole place of work knows the truth, and instead of doing what anyone else would do in that situation, Andy actually sticks around and allows himself to be helped in getting laid – which naturally leads to more and more awkwardness.

It’s hard to pick the most terrible moment, the first that comes to mind would be his inebriated foreplay scene with Elizabeth Banks’s super sexual Beth character, or probably worse would be his near fatal ride home with director Judd Apatow’s wife Leslie Mann who drunkenly drives Andy back to her place, only to give him a taste of the contents of her stomach. Probably the best moment has to be the speed dating, when Andy is attacked by his own awkwardness when confronted with a very talkative lady who probably should have considered wearing a bra.


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