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  1. Entertainment
  2. Movies

50 Most Awkward Movie Moments

Features
By Simon Kinnear
Published 10 September 2012

Excruciating embarrassment alert

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Borat (2006)

The Movie: Sacha Baron Cohen arrives in America disguised as Kazakh journalist Borat Sagdiyev, determined to do mischief.

The Awkward Moment: Attempts to educate Borat in Southern civility flounder when he causes uproar at a posh dinner by bringing prostitute Luenell to the house.

Look Away When: Borat returns to the table from a loo break, still clutching his poo in a plastic bag.

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Pulp Fiction (1994)

The Movie: Quentin Tarantino's multi-strand epic features so many characters trapped in weird situations that the awkwardness factor is high throughout.

The Awkward Moment: Winston Wolf (Harvey Keitel) has turned up to deal with 'the Bonnie situation,' but Vincent Vega (John Travolta) risks everything by getting shirty because Wolf didn't say "please."

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Look Away When: Vincent and Jules (Samuel L. Jackson) end up on car-cleaning duty. As Jules says, "this is some fucked-up repugnant shit."

Planes, Trains and Automobiles (1987)

The Movie: John Hughes' mismatched-buddy comedy sees uptight Neal Page (Steve Martin) have to make his way home for Thanksgiving in the company of slobbish Del Griffith (John Candy).

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The Awkward Moment: The two men have to share a bed.

Look Away When: Realisation dawns as to where Del's hand is. "Those aren't pillows!" screams Neal.

Fast Times At Ridgemont High (1982)

The Movie: If Amy Heckerling's high school comedy rings painfully true, that's because Cameron Crowe's screenplay was based on his own undercover research.

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The Awkward Moment: Brad Hamilton (Judge Reinhold) knocks one out over his sister's best friend, Linda (Phoebe Cates).

Look Away When: Linda walks in on Brad and the best he can manage is outrage: "Jeez. Doesn't anyone fucking knock any more?"

Young Adult (2011)

The Movie: Jason Reitman and Diablo Cody turn the screws on an aging-but-still-immature generation that can't let go of the past, via the hideous presence of selfish kidult author Mavis Gary (Charlize Theron).

The Awkward Moment: Mavis has returned to win back high-school crush Buddy (Patrick Wilson), only to hear his current wife playing a cover version of Mavis and Buddy's old song, Teenage Fanclub's The Concept .

Look Away When: She reminds him it was the song playing the first time she went down on him.

Meet The Parents (2000)

The Movie: What could be more awkward than meeting your partner's parents? For Greg Focker (Ben Stiller), finding out his future father-in-law is creepy CIA vet Jack Byrnes (Robert De Niro), that’s what.

The Awkward Moment: Greg and Jack come to blows over the latter's milkable cat, Mr Jinx. "You can milk just about anything with nipples," reckons Greg. "I have nipples, could you milk me?" retorts Jack.

Look Away When: At the same meal, Greg accidentally demolishes the urn containing the ashes of Jack's mother.

Fargo (1996)

The Movie: Never mind the Coen brothers' tale of kidnap and murder in the Minnesota snow, Fargo is also the story of happily-married, about-to-drop police chief Marge Gunderson (Frances McDormand).

The Awkward Moment: Marge takes a break from the case to meet old school friend Mike Yanagita (Steve Park), only to discover he's hoping for more than a chat.

Look Away When: Mike starts sobbing. "You were such a super lady. And I'm, I'm so lonely."

Four Weddings And A Funeral (1994)

The Movie: The clue's in the title.

The Awkward Moment: A table plan snafu sees Charles (Hugh Grant) seated amongst a posse of ex-girlfriends who are only too happy to spill the communal beans.

Look Away When: The girls discuss a fellow ex they knew only as Miss Piggy. Turns out she's at the table, too, but has "lost a lot of weight since then."

The Graduate (1967)

The Movie: Mike Nicholls' era-defining comedy reminded that the Sixties didn't just swing for the kids.

The Awkward Moment: A nervous Benjamin Braddock (Dustin Hoffman) tries to book a room for his affair with Mrs Robinson (Anne Bancroft) from a suspicious clerk (Buck Henry).

Look Away When: Asked about luggage, Ben panics and says the porter shouldn't bring it in because "I only have a toothbrush."

Vertigo (1958)

The Movie: The new "greatest film ever made," according to the critics, sees Alfred Hitchcock making us uncomfortable over voyeurism and necrophilia.

The Awkward Moment: Scottie Ferguson (James Stewart) drags Judy Barton (Kim Novak) into a shop to give her an unusual makeover - he wants her to look just like Madeleine Elster, the woman he loved and lost [little realising that Judy is Madeleine].

Look Away When: Scottie starts on her hair - "Judy, please, it can't matter to you."

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