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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