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Sarah Paulson and Matthew Perry -

Sarah Paulson and Matthew Perry both manage to be awkward enough on their own, but also have a hilariously awkward tale together. 

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Sarah Paulson and Matthew Perry - The 'American Horror Story' actress recalled the story on 'Jimmy Kimmel Live!' in 2021, which started by meeting Carrie Fisher at a party at an executive's house, E! News reports. They hit it off, and Fisher invited Paulson to another party afterwards, which Fisher reportedly coined "Gore Vidal's make-out party," and was supposedly a star-studded affair.

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Sarah Paulson and Matthew Perry -

What is a make out party? "There was a hat with names in it and you were supposed to make out with whomever you pulled out of the hat," Paulson explained. She ended up being one of the names pulled, but the result was more awkward than kissing a stranger. "Matthew Perry pulled my name out of the hat," she said, "and then promptly left the room." To make matters worse, she said the 'Friends' alum actually told her he pulled out her name. "I was like, 'Uh, well let's kiss!'" Paulson recalled, "and he was like, 'No.'"

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Britney Spears - The Princess of Pop is also the Princess of Oops, constantly forgetting the names of people and places, putting on strange accents, and not realizing that her mic is on when she decides to go on a rant backstage. 

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Quentin Tarantino - The director is known for bluntly putting down journalists, like telling a female reporter who asked about Margot Robbie's lack of lines, "Well I just reject your hypothesis." He's also told Krishnan Guru-Murthy, when asked about the link between on-screen and real-life violence, "I'm shutting your butt down!" 

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Taylor Swift - You need only watch Swift dancing to feel the second-hand awkward, but add to that the endless drama with her exes and nemeses and it's like a car crash you can't look away from. 

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Robert Pattinson - Nothing is more awkward than watching Pattinson respond to questions about 'Twilight.' When he was asked which of his coworkers made his experience the most rewarding, he pondered it for an excruciatingly long time and then said, "SK-II Face Packs." Cream. His answer was cream.  

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Jennifer Lawrence - Tripping over her dress, spilling mints at a press junket, and describing her outfits on the red carpet with, "What do you mean? Like this is the top...and this is the bottom," J-law is an awkward icon.

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Michael Cera - Soft-spoken and hesitant, with a strange posture and sense of style, Michael Cera is the quintessential awkward celebrity.

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Katy Perry - After Neil deGrasse Tyson asked the pop singer about the role of math and science in her life, she asked, "Is math related to science?" At least she was honest.

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Katy Perry - There are too many moments to choose from! From belly-flopping onto a huge cake to her cringe-worthy dance moves with Migos on 'SNL', the singer makes a lot of bad decisions. 

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Miley Cyrus - Many people actually compared Katy Perry's awkward moment on 'SNL' to Miley Cyrus' cringe years of twerking, dreads, nudity, and feuding with Nicki Minaj.

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Bill Murray - Known for showing up when you least expect him and doing whatever weird thing he feels in the moment, Murray seeks out awkward moments, like stealing people's fries and telling them, "No one will ever believe you!" 

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Aubrey Plaza - That dead look in her eyes and her tendency to say very strange things are Plaza's trademark. Accepting an award on behalf of Amy Poehler, she said, "I'd like to thank the devil, and all the dark lords who gave her this award, allowed her to feast on the flesh of the innocent—" before being dragged off by Chris Pratt.

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Johnny Depp - The mumbling, slurred speech, the dry interview answers, and that time when he went up to accept his award for Favorite Movie Icon and started with, "It's blue! Did you guys notice that?" all elevate Depp's awkward vibe. 

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Tom Cruise - While he's been mega famous for three decades, Cruise has become something of an awkward character, from jumping on Oprah's couch to arguing with Matt Lauer about the evils of Ritalin. Many also scrutinize his dedication to Scientology.

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Cardi B - If she's not afraid to tweet about her farts, there is really no line for the rapper. On the Grammys red carpet, she was simply asked how she was feeling, and she responded candidly, "I'm feeling butterflies… in my stomach and vagina!"

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Christopher Mintz-Plasse - The actor behind some generation-defining nerds, most notably McLovin from 'Superbad,' is just as awkward off-screen. Who else would give a thumbs-up at a Playboy event?

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Samuel L. Jackson - It's not that he's awkward, but rather that he thrives in the awkward situations he's forced into. When a news anchor confused him with Laurence Fishburne, he responded, "We don't all look alike!" and appropriately ridiculed him, then later wore a t-shirt that said, "I'm not Laurence Fishburne."

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Kristen Stewart -

The unsmiling star looks uncomfortable everywhere, but especially when the cameras are on. Plus who could forget that time she dropped her MTV award on-air?

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Rachel Dratch - The famed 'Saturday Night Live' star is inseparable from her awkward characters like Debbie Downer and the deadpan teen boy from Wake up, Wakefield.

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Zooey Deschanel - The actress is responsible for popularizing the whole "adorkable" thing.

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Hugh Grant -

Hugh Grant, whom you might think would have a little more ease after being in Hollywood for years, made quite an awkward impression at the 2023 Oscars. It began with his red carpet interview with Ashley Graham in which he gave completely lackluster responses to her very standard questions. When she asked if he was looking forward to seeing anyone win, he replied, "No one in particular," and when she asked what he was wearing he said, "My suit," whom he clarified was by "my tailor." Graham asked about his appearance in 'Glass Onion' and he shut it down by saying, "Well, I'm barely in it. I’m in it for about three seconds," and after she politely thanked him for his time he awkwardly turned side to side and raised an eyebrow.

It only got harder to watch as he presented an award alongside his 'Four Weddings and a Funeral' co-star Andie MacDowell. Grant emphasized "the vital importance of using moisturizer," pointing out that McDowell has been using one "for the last 29 years, and I've never used one in my life." He gestured to her and said, "Still stunning," then gestured to himself and said, "Basically a scrotum." At least the audience erupted in laughter!

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Jim Carrey - At New York Fashion Week, a reporter noted that she'd never seen him at a fashion event like this, and he replied, "There's no meaning to any of this, so I wanted to find the most meaningless thing that I could come to and join and here I am." Smooth.

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Ben Stiller - Ben Stiller is a talented and hysterical actor who can speak eloquently in interviews, but he has played the "awkward guy" role so perfectly and repeatedly that it's almost weird to see him not tripping over his own feet.

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Joaquin Phoenix -

In the years leading up to the release of his documentary—later revealed to be a mockumentary—called 'I'm Still Here,' Phoenix completely fooled people with extremely awkward interviews and bad rap performances.

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Jay Baruchel - Baruchel is almost always cast as the "awkward guy," and it's because he's really good at both looking and sounding uncomfortable.

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Jesse Eisenberg - From 'The Social Network' to 'Zombieland' to 'Now You See Me,' the actor has perfected the role of an over-confident, socially awkward character, helped immensely from his fast-paced and monotone speech.

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Zach Galifianakis - His squirm-inducing characters are brilliant and perfectly awkward, as is the now-infamous 2010 interview during his press tour for 'It's Kind Of A Funny Story,' which keeps resurfacing every few years because of its cringe factor.

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Larry David - You have to have a close relationship with awkwardness if you're going to make a show like 'Curb Your Enthusiasm.' There's even an academic paper called "Awkwardness, or the Cultural Logic of Larry David."

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Donald Trump - His social and political gaffes are far too many to count, from spelling errors to smiling with orphaned babies, and the tweets keep on rolling.  

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David Blaine - The famous magician can make people gasp in shock just as much as he can make them completely uncomfortable with his monotone drawl and unwavering eye contact.

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Thomas Lennon -

The booty-short wearing Lieutenant Jim Dangle from 'Reno 911!' has perfected the art of making audiences uncomfortable with his long, awkward stares and offbeat sense of humor.

See also: The most awkward and hilarious royal moments.

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