The 6 Most Awkward Characters To Ever Make You Cringe

Millman, "Extras"

Ricky Gervais' sitcom "Extras" doesn't have the same reputation as his earlier hit "The Office," but the awkward moments are exponentially more potent. "Extras" features some of the most unwatchably hilarious awkward encounters in the history of comedy, most of which stem from Andy's desire to be seen as a serious artist and not the bumbling, arrogant boob he really is.

Rupert Pupkin, "The King of Comedy"

Martin Scorsese's 1983 film predicted the "awkward comedy" movement in many ways, even though taken by itself it's often more depressing than funny. Robert De Niro plays Rupert, an aspiring stand-up comedian who wants nothing more to be famous, and who stages pretend talk shows with himself and guests in his mother's basement. His plan for fame includes kidnapping late night TV host Jerry Langford at gunpoint and hijacking his show. The most awkward scene comes before that, though-when Pupkin obliviously invites himself and a date into Langford's home only to be humiliatingly rebuffed.

Napoleon Dynamite, "Napoleon Dynamite"

Harold Lloyd was a silent film comedian who was adept at playing socially awkward young men. And his most socially awkward young man is probably Meadows here, who's so deathly afraid of women that whenever he's forced to communicate with one he goes into an excruciating stutter that can only be eased by a loud noise or jolt. So he does what any person in his situation would do-write a book about how to pick up women.

Hrundi V. Bakshi, "The Party"

In Blake Edward's swinging '60s comedy "The Party," Peter Sellers plays a luckless actor from India who accidentally gets invited to a swanky Hollywood party.  From the moment he steps into the door, things start to go wrong, whether it be Hrundi bumblingly flirting with a girl or trying to get an autograph from a famous Hollywood star to accidentally activating the sprinklers outside.