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.

–~~~~~~~~~~~~–

5. American Pie

You know, usually if a movie’s title and advertising campaign – poster included – is based solely around a dude sticking it to an apple pie, that’s most likely a sign that the film isn’t going to be good…or that it’s going to be brilliant. It’s one or the other, and for the life of me I can’t figure out which this movie is.

All I know is that it opens with what has to be the most uncomfortable moments in a teen film when a young man is barged in on by his parents whist he is getting his rocks off to blurry cable soft-core porn. It’s that nightmare scenario that all adolescent boys fear, and they give it to us with no sugar coating. We’re forced to watch it play as brutally as any torture scene might. It’s downright unbearable – and then only gets worse as his father, played by the brilliant Eugene Levy, is now determined to make this a bonding experience by having several heart-to-heart talks with his son about sex throughout the rest of the film. The worst of the bunch has to be when he presents his son with a collection of porno mags, and then proceeds to go through the pages with him while making awkward commentary about each picture. It’s truly painful. And none of this includes our title character, the pie. That’s a whole different moment entirely.

4. Eyes Wide Shut

This isn’t exactly the first movie that comes to mind when you think of awkward – but go watch it again and tell me it’s not one of the most uncomfortable movies to watch. This final Kubrick film follows Tom Cruise around as he desperately attempts to have an affair on his wife, only to stumble through one uncomfortable encounter after the next until finding the ultimate moment of humiliation as he is confronted at a super-rich guy masked orgy in which he was not invited, and forced to expose his face to everyone attending. What makes this so horrible is that, as a rich doctor for rich people, most of the masked attendees surely recognize him.

It’s not just this event either – every conversation he has with people comes across as weird, even the stoned argument he has with his wife is hard to bear due to how uncomfortable the subject matter is. The worst conversation of all has to be when Cruise returns to the house of a prostitute who he failed at having sex with the following day, this time determined to go through with it. He discovers that the woman isn’t home and makes an attempt to lay her roommate instead, only to find out from her that the woman he almost slept with the night before just found out that she has HIV – a bullet that he had thankfully dodged. Imagine a Tom Cruise trying to nail you, and you having to try to tell him that he might have AIDS at the same time. Really imagine it.

3. Superbad

Oh, Lord yes. Everything in this film is just so terribly adolescent and tumultuous. Where to start? McLovin making a flaccid attempt at passing as an adult, Jonah Hill and Michael Cera crashing a scummy coke party, so many wonderful moments. You especially have to love when, trapped in a room full of coked up strangers at the party, Cera’s character Evan is forced to lead a sing-along. Meanwhile something terrible is happening to Jonah Hill’s pant leg on the dance floor. All of this effort made in an attempt to pass one of the ultimate teenage challenges that exists: getting alcohol. Naturally they are acquiring the booze as a means to hook up with two very attractive young ladies in their class, a mission that goes…less than good.

The scene that Cera’s character spends the entire film attempting to accomplish – the sex scene – is also the apex of his awkwardness as he is jumped by a very drunk girl, played by Martha Maclsaac, and has no idea how to properly handle the situation. It’s that wonderful ethical limbo that a sober person faces when confronted by a very drunk and attractive individual who is ready for love. What does one do? Thankfully, the answer becomes clear in the form of vomit.

If you ask me, the most embarrassing scene has to be way earlier in the movie when Evan accidentally punches his crush in the boob while at school. It’s not that moment exactly, but it’s what comes afterward when their clumsy interaction is finally over and they both part ways…in the same direction. We can all relate to that, and Evan handles it the only way one can, by awkwardly walking faster.

2. Swingers

In terms of social awkwardness there is nothing that beats out this film. It’s so simple: two guys trying to get numbers. Not even laid – well, sometimes laid, but mostly it’s about getting to the bar, starting a conversation, getting a number, and then calling her after two, no three…six days or so. It’s the combination of our main characters, played by Jon Favreau and Vince Vaughn that make it really work. We have one guy whose self-esteem has been beaten down by a past and lingering relationship and another guy who plows through bar life as a self-crowned gift to women. Both men are equally lovable and clueless, and their attempts to look successful and classy are negated by their immense ineptitude. This is evident right away as the two of them hit of Vegas and toss down three hundred at a black jack table, only to receive three chips in return – as the table has a $100 minimum. Instead of walking away, they try to roll with it and sit down with their three chips.

That’s really the core of their issues – every time they dig a hole, they refuse to backtrack and instead attempt to tunnel out. The best moment of this is when Favreau’s character Mike mans up and calls back a number he scored from an interaction earlier. When he is given her answering machine he opts to take the less traveled route and leaves her a very awkward message. Instead of hanging up and letting it go, he dials her again in an attempt to save face from before – once more leaving an even worse message. This keeps going as he fills up her answering machine with a series of messages that just get worse with each call as he runs through an entire arch of conversation with himself that ends with him deciding that maybe he and this girl (who he has yet to actually speak with) should take some time away from each other. This is confirmed when she finally does pick up, only to tell him to stop calling her.

None of this is comparable to the very last scene of this film, which I will not spoil. All I can say is that it pretty much sums up the horrible awkwardness of these guys in one very simple interaction.

1. The Room

Oh, hi, number one selection!

This film…well it’s not the kind of awkward you were expecting, no doubt, but it is way, way worse than any of the other ones on this list. Why? Because the inept and embarrassing characters, dialogue, and plot points of this film is completely unintentional – making them so, so much worse to watch.

Directed, written, produced by, and starring the terrifying Tommy Wiseau – this thing has become a bit of a cult hit over the years for being one of those “so bad it’s good” movies. It has resulted in interactive screenings with the same kind of fan base and energy as a midnight viewing of Rocky Horror, as well as one of the best Rifftrax ever. It’s amazing to watch with friends and baffling to analyze. And if you have the chance, I dare you to watch it alone with no commentary. It’s the hardest thing you can possibly watch. The reason why is that it’s only watching it in this straightforward condition that it dawns on you that this ridiculous film actually has a full cast and crew. People actually worked to make this – there are sex and fight scenes that are both embarrassingly choreographed. Money was put into it.

It’s almost impossible to imagine how nobody working on the film would think that what they were doing was a good idea. When Lisa’s mother tells her that she has cancer and Lisa replies with a nonchalant “Don’t worry about it,” why was it that nobody stopped and said: “Wait, this is stupid”? It’s like some kind of mass insanity where everyone is so wrapped up in following orders and achieving each simple task that they don’t bother to step back from it all and reflect. As funny as watching the end result is, you can’t help but to feel embarrassed for every poor soul that appears on the screen.

So awkward.

Get awkward with more Cinematic Listology


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