In this weekend’s That Awkward Moment, Zac Efron, Miles Teller and Michael B. Jordan play three twentysomething friends who find themselves in some hilariously awkward and embarrassing situations while navigating the tricky terrain of modern-day romance. In celebration of the film’s release, here’s a look back at some of our favorite, guy-centric “awkward movie moments.”
American Pie (1999) In a film loaded with amusingly awkward moments, none is quite as discomfiting for its lead character, Jim (Jason Biggs) – and audiences - as when his parents walk in on him, ahem, pleasuring himself. This hilarious opening scene set the perfect tone for the outrageously frank look at teen sexuality to follow.
There’s Something About Mary (1998) Speaking of frank, poor Ben Stiller gets both his frank and beans stuck in his zipper on prom night in this classic awkward movie moment. If it isn’t bad enough having his date’s (Cameron Diaz) parents try and help him out, pretty soon the whole neighborhood’s aware of his painful - and painfully funny - predicament.
Planes, Trains & Automobiles (1987) In this John Hughes holiday classic, Steve Martin and John Candy play a pair of unlikely companions who agree to travel together cross-country after their flights are canceled. Forced to share a motel bed one night, the two wake up the next morning sharing an awkward moment of unexpected intimacy.
Wedding Crashers (2005) In this smash hit wedding comedy for guys, Vince Vaughn’s character gets an unexpected helping hand from the daughter (Isla Fisher) of U.S. Treasury Secretary William Cleary (Christopher Walken) during a formal wedding weekend dinner. Thankfully, Vaughn’s got wingman Owen Wilson by his side to help turn any uncontrollable utterances into appropriate dinner-table conversation.
The 40-Year-Old Virgin (2005) Steve Carell made his name in comedy playing awkward bosses, awkward dinner-party guests and, most famously, an awkward, 40-year-old virgin named Andy in Judd Apatow’s hit movie of the same name. In this hilarious “awkward moment,” Carell tries to deny his virginity to his poker buddies but his lack of basic sex vocabulary (“I’ve borked a lot of women in my day”) kind of gives him away.
Dumb & Dumber (1994) In this Farrelly brothers’ classic, Harry (Jeff Daniels) gets an unfortunate case of the number two’s right at the start of his date with gorgeous and wealthy heiress Mary (Lauren Holly). Things get even more unfortunate when he learns her bathroom toilet doesn’t flush.
Swingers (1996) Sometimes it’s not what a guy does but what he says – or struggles to say – that creates memorable movie awkwardness. In this increasingly painful-to-watch sequence, Jon Favreau’s character tries and tries again – and again – to leave the perfect answering machine message for a girl he just met.
Annie Hall (1977) Woody Allen is famous for playing amusingly bumbling and anxious characters on-screen like Annie Hall’s Alvy Singer, who awkwardly attempts to play it cool in front of love interest Annie Hall (Diane Keaton) and her friends by trying cocaine for the first time. Let’s just say he blows the moment.
Old School (2003) In this guys-gone-wild comedy, three friends (Will Ferrell, Vince Vaughn and Luke Wilson) attempt to recapture their college glory days by opening up a frat house. In one of the film’s funniest scenes, Frank the Tank (Ferrell) drunkenly believes he’s leading a pack of streaking partygoers – until his humiliated wife drives by with her friends.
Superbad (2007) In this grade “A” high school comedy, Michael Cera, the one-time reigning prince of on-screen adolescent awkwardness, attempts to hit on classmate Becca (Martha MacIsaac). Unfortunately, hit become the operative word in our final awkward movie moment.
Tell us about your favorite “awkward” movie moments in the comments section below and don’t forget to check out That Awkward Moment in theaters everywhere today.
