Awkward moments at the movies

Did you know there is an annual day devoted to the celebration of
awkward moments?

Well, now you know that day is – wait for it – today. Yes, today. National Awkward Moments Day happens to coincide with the beginning of National Introverts Week, meaning this week – and this day in particular – is custom-made for me and those like me, God have mercy on their souls.

Bringing this around to the topic of movies (that is the point of this site, after all), I admittedly had a difficult time thinking of my favorite awkward moments in movies, which is not to be confused with my favorite awkward moments in a movie theater. But that’s for a different post, and I digress. At any rate, these days it feels like TV is more fertile ground for cringe-worthy moments, what with folks like Larry David, Nathan Fielder and Eric Andre still cranking out high-quality awkwardness.

Still, these are my personal five favorite of filmdom’s awkward moments…

5. Annie Hall

Long before Christopher Walken became the Christopher Walken we know and love, Woody Allen saw something strangely wonderful in the then-33-year-old actor. Although Walken is in only one scene in 1977’s Oscar-winning Annie Hall, he is memorable as the younger brother of the titular character. Moreover, the scene is a sort of harbinger for a career specializing in awkward moments.

4. Meet the Parents

Ben Stiller has two chief comedic shticks. Either he plays a goofy buffoon (think Zoolander or Dodgeball: A True Underdog Story) or he’s a beleaguered loser under siege by an unforgiving universe (think his romcoms). While a strong argument can be made for Stiller’s cringiest moment being the penis-in-zipper scene that opens There’s Something About Mary, my personal preference arrives in 2000’s Meet the Parents. In the initial dinner with his girlfriend’s parents, Stiller’s Greg Focker comes off as a jackass and weirdo. Robert De Niro is the perfect straight man/foil as Jack, the no-nonsense father who forces Greg to dig himself a deeper hole.

3. Back to the Future

Robert Zemeckis’ monster hit of 1985 was the rare animal that struck all the right blockbuster notes – high concept! cool action! popular theme song! – while not being afraid to get freaky. Few mainstream movies are so delightfully twisted as to get Oedipal, but Back to the Future goes there when Marty McFly (Michael J. Fox) travels in time to 1955 and meets his parents when they are high school students. When his future mom, played by Lea Thompson, makes it clear she has the hots for this stranger she thinks is named Calvin (after all, it’s embroidered on his underwear), Fox’s guarded reaction is straight-up hilarious.

2. Borat

Sacha Baron Cohen has made a nice living testing the limits of appropriate human interaction. When he parlayed his successful TV series, Da Ali G Show, to the big screen in 2006, Baron Cohen turned to one of his stock characters, Borat, a dense, antisemitic and altogether creepy correspondent from the fictitious country of Kazakhstan. Baron Cohen and director Larry Charles then scoured the nation looking for stomach-churning comic gold. Essentially an extended Baron Cohen improv, Borat has a lot of cringey to choose from, but my personal fave is Borat’s participation in a formal dinner party in the supposedly well-mannered South.

1. Happiness

Like Borat, this is a movie bursting at the seams with cringe. Writer-director Todd Solondz is to awkward moments what Kanye West is to batshit crazy: They are both dubious masters in a particularly dubious field. While this blacker-than-black 1998 comedy is rife with awkwardness — a central storyline involves a pedophile therapist, if that gives you any indication — I opt for Philip Seymour Hoffman as an obscene phone caller who somehow lands an ill-fated date with Lara Flynn Boyle as the object of his dark obsessions. Sadly, I can’t find a clip of that scene online, so you’ll either have to be content with the still pic below or hunt down the movie. But be cautioned: Happiness is not easy to find (the film, that is, although the state of mind is no pushover, either) and it is definitely not for the faint of heart.