50 Most Awkward Movie Moments

L.A. Confidential (1997)

The Movie: In Curtis Hanson’s retro-noir thriller, L.A. is home to Hollywood stars…and prostitutes cut to look like Hollywood stars. But who can spot the difference?

The Awkward Moment: Ed Exley (Guy Pearce) angrily interrogates gangster Johnny Stompanato (Paolo Seganti) and his girlfriend (Brenda Bakke), who Exley assumes is a Lana Turner-lookalike whore.

Look Away When: “She is Lana Turner” – and the actress throws her drink in Exley’s face.

Ted (2012)

The Movie: Thirtysomething slacker John Bennett (Mark Wahlberg) needs to grow up fast to keep girlfriend Lori (Mila Kunis). Not easy when John’s best friend is a sentient, slobbish teddy bear (Seth MacFarlane).

The Awkward Moment: Ted pulls strings so that John can serenade Lori from the stage of a Norah Jones gig.

Look Away When: John starts singing Octopussy theme tune All Time High in totally the wrong key.

Lolita (1962)

The Movie: Stanley Kubrick makes the unmakeable, adapting Nabokov’s infamous satire about paedophile Humbert Humbert (James Mason) and his desire for step-daughter Lolita (Sue Lyons).

The Awkward Moment: Humbert, hoping to find a quiet hotel with Lolita, discovers it is full of police officers… and one of them, in fact fellow paedophile Clare Quilty (Peter Sellers) going incognito, won’t leave Humbert alone.

Look Away When: Quilty sleazily notes, ” I wish I had a lovely daughter like that.”

No Strings Attached (2011)

The Movie: Beating the similarly themed Friends With Benefits into cinemas, this is the one where Natalie Portman and Ashton Kutcher make a pact to become fuck-buddies.

The Awkward Moment: When Emma (Portman) invites Adam (Kutcher) to meet the family, he shows up in a bright yellow sweatshirt, not realising the event is a funeral.

Look Away When: Emma compounds his embarrassment by denying that she’s dating Adam – “I’m not. I just had a one night stand with him when I was fourteen.”

Bridesmaids (2011)

The Movie: Paul Feig’s hit comedy sees trouble-magnet Annie (Kristen Wiig) trying – and failing – to step up to the duties of chief bridesmaid for best pal Lillian (Maya Rudolph).

The Awkward Moment: Scared of flying, Annie wrecks the trip to the hen party after taking a dangerous mix of alcohol and sedatives.

Look Away When: Annie remonstrates with steward Steve (aka “Stove”) by doing Hitler impersonations.

Chungking Express (1994)

The Movie: Wong Kar-Wai’s zippy Hong Kong drama sees two would-be romances floundering, the second one largely because infatuated Faye (Faye Wong) is pretty much stalking Cop 663 (Tony Leung).

The Awkward Moment: Faye has been breaking into 663’s apartment for a while, but has to think fast when he comes home while she’s still there.

Look Away When: Faye gives a terrible response to what she’s doing there – “you asked me to visit you.”

Monster (2003)

The Movie: This biopic of serial killer Aileen Wuornos – played by an unrecognisable, Oscar-winning Charlize Theron – lifts the lid on the American dream.

The Awkward Moment: Aileen goes for a job interview and is heckled by her would-be employer – “when the beach party is over, you don’t get to say: You know what? Now I think I’d like to have what everybody else has worked their entire life for.”

Look Away When: Aileen’s placid facade crumbles and she spits back, “Fuck you!” with unexpected venom.

Wedding Crashers (2005)

The Movie: Along with pal John Beckwith (Owen Wilson), Jeremy Grey (Vince Vaughn) has a great plan – crash weddings to get laid. Until he meets crazy Gloria Cleary (Isla Fisher).

The Awkward Moment: Invited to a posh dinner at the Clearys’ house, Jeremy certainly isn’t expecting Gloria to give him an impromptu hand job under the table.

Look Away When: The camera cuts to a close-up of Gloria’s hand rubbing Jeremy’s crotch.

The Empire Strikes Back (1980)

The Movie: Blockbuster sci-fi sequel – or screwball comedy about the growing romance between Han Solo (Harrison Ford) and Princess Leia (Carrie Fisher)?

The Awkward Moment: Leia tries to rebuff Han’s help aboard the Millennium Falcon. “My hands are dirty.” “My hands are dirty too. What are you afraid of?”

Look Away When: C-3PO interrupts a near-kiss. If looks could kill droids, Han’s withering glare would do the job.

Y Tu Mama Tambien (2001)

The Movie: Alfonso Cuaron’s movie is – depending on your viewpoint – a subtle satire about the Mexican class system, or a brainy sex comedy about two teenagers with the horn for an older woman.

The Awkward Moment: Tenoch (Diego Luna) finds Luisa (Maribel Verdú) crying; his stilted attempts to console her turn into an unexpected clinch.

Look Away When: They have sex, but a carried-away Tenoch climaxes almost immediately.

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