20 Most Awkward Celeb Photos Taken At Exclusive Hollywood Parties

When the cameras are on, celebrities are at work. They understand how important image is to their celebrity status, and they know the scrutiny that comes with slipups. For the most part, the stars maintain their composure. Some make mistakes and look foolish in public, but, most of the time, they stay perfectly grounded. But what happens when celebs think that they’re in a safe zone? What happens when they let their guards down? It’s often in these places that celebs are caught in the most awkward and compromising positions. It becomes dangerous when they feel comfortable because, for a celebrity, comfort is the devil’s pitchfork. It’s possible that the more exclusive the party the more comfortable a celebrity gets, but we know that’s not always true. After all, there’s a social hierarchy in Hollywood as well.

Humans are awkward creatures. We don’t necessarily need comfort or parties to allow us to make a fool of ourselves. We can do that without any help. Celebrities are the same. That’s why we have many examples of these stars embarrassing themselves. In many of these situations, the awkward celeb just happened to be at an exclusive party at the time. So, today, we take a look at all the different types of celebrity awkwardness at some of Hollywood’s most exclusive parties. For those photos that aren’t obvious, we will explore why the moment captured in the photo is so awkward. Here are the 20 most awkward celeb photos taken at exclusive Hollywood parties.

20 Paul McCartney Post-Grammy Party

As Paul McCartney watched The Dark Knight, it’s unlikely that he thought Harvey Dent was speaking about him when he said, “You either die a hero, or you live long enough to see yourself become the villain.” Now, we want McCartney to live forever, but it is sad to see a music legend, part of one of the greatest bands in history, get turned down from a Grammy’s after party. It’s even worse, salt in the wound, if you will, that the party was apparently hosted by Tyga.

Now, according to Vanity Fair, Tyga didn’t actually host the party. He simply performed, which means that McCartney probably wouldn’t have enjoyed the party much anyway.

That’s maybe why Woody Harrelson looks so embarrassed. He just found out that what they thought was a live tiger inside the club was actually just a rapper known for dating Kylie Jenner.

19 Sean Young Taken Away From The Governor’s Ball

Technically, a photographer snapped this photo of Sean Young after an exclusive party, the post-Oscar Governor’s Ball in 2012. Still, the party helps provide the photo with context. That’s important. Allegedly, a security guard outside the Governor’s Ball asked Young to leave after she didn’t produce a ticket to get in. She refused. The security then asked again, which got the same answer.

According to The Hollywood Reporter, it’s then that the security guard is said to have tried to escort Young away.

For this, Young apparently slapped him. The police came and arrested her. After Young posted the $20,000 bail, she exited the police station and met the cameraman who took this photo. This isn’t the only time Young’s found herself in trouble during an award show, but it is the best picture.

18 Sophia Loren And Jayne Mansfield

This 1957 photo of Sophia Loren and Jayne Mansfield is one of the most famous Hollywood photos in history. Not only does it include two icons in the waning Golden Age of Hollywood, but there is a great story to the picture as well. Obviously, Loren’s side glance tells us almost all we need to know.

There is no confusion or no misunderstanding here either. Loren is looking exactly for the reasons we think she’s looking.

Paramount threw this party of the Hollywood elite for Loren as an introduction of sorts. In an interview with Vanity Fair, Loren explains that Mansfield came late and sat down next to her at the table. While this photo captures the thought in process, Loren suggests that she was thinking the same thought the entire night: Is she going to fall out of that dress?

17 Selena Gomez At Vanity Fair Party

Watching Selena Gomez try to manage to carry on with her life after the Vanity Fair Oscar after-party in 2015 should be an Olympic sport. Seen here in three shots, we seem to have Gomez either sleeping on her feet or realizing that she is not able to stand up any longer. The next shot appears to capture Gomez distraught, either about her condition, her choice of seat, or both.

Here we have Gomez finding her zen. While the seat choice on the dirty ground may not have been optimal, it seems to have done the trick.

While there are reports, such as those from The Daily Mail, that Gomez’s condition may be influenced by the fact that she ran into her ex-Orlando Bloom and his ex-Miranda Kerr, but that’s not been confirmed. It’s more than likely that Gomez just had a lot of fun and, sometimes, a lot of fun ends with agony sooner than anticipated.

16 Joan Crawford’s Last Party 

In 1974, Joan Crawford retreated from public life to tend to her health. She wasn’t acting and required a few dental surgeries, so the time away from cameras was appreciated for the screen legend. Later in the year, however, she decided to come out for a friend’s party at the Rainbow Room in New York. Photographers and videographers took to the exclusive party to capture Crawford and many of the other stars and artists in attendance.

According to CBS, this would be Crawford’s final public appearance.

The morning after the party, Crawford picked up the paper to see what the press captured and saw her photos. Reportedly appalled, Crawford said, “If that’s the way I look, they’ve seen the last of me.” After that, Crawford canceled her remaining public commitments and lived as a recluse.

15 Kate Winslet Kisses Leo’s Chin

Leonardo DiCaprio brings out the awkward in almost everyone. It doesn’t matter if you’re a superstar on your own and a long-time friend of the star like Kate Winslet, they all geek out a little. That’s what this exclusive Golden Globe after party brought us, an event photographed by The Daily Mail. It appears to be January Jones with Winslet, but we can’t be sure. That doesn’t matter anyway. Look at Winslet’s greeting for Leo.

As the actress goes in for the kiss, which we presume was meant for Leo’s lips or cheeks, she kisses him square on the chin.

Now, Leo’s taking the chin kiss as if he asked for it to happen, but we imagine it didn’t exactly play out that way. And look at Elton John in the background. He’s thinking, Is she-Oh, she’s done it. Kissed him on the bloody chin.

14 Michael B Jordan Rejected By P Diddy

When Michael B. Jordan and his posse approached the doors to P. Diddy’s BET after party, the star had to think that he would be ushered in without objections. But that wasn’t the case. In fact, Jordan was turned down at the door. According to TMZ, the club was at capacity. Humbly, Jordan walked back to his vehicle accepting that these things happen.

Then, from the club, a representative for Diddy came out and asked Jordan and friends to come back. They did. Amazingly, they got turned down at the door again. Now, Jordan is visibly annoyed, citing, “drama in L.A.” This time, after retreating back to the car once again, Jordan and friends drive off. Shortly afterward, another representative comes out trying to hail them down. This is when we see Diddy approach the doorman and club owner to see why Jordan was rejected. We assume Diddy reached out to Jordan to apologize for the awkward mix-up.

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13 Christoph Waltz And His Burger

There’s a chance that at this afterparty that Christoph Waltz is attending, burgers in fast food wrappers were being served. However unlikely it may seem, it’s possible. The real interesting part about this awkward photo is the anger beaming from Waltz’s eyes. It seems that he’s not fond of being snapped by US Magazine eating his burger at a glitzy event, but maybe he’s just playing a character.

If you got through the 2015 photos of the Golden Globe after party, Waltz and his cheeseburger show up numerous times in different places.

Either he ate several burgers, he eats very slowly, or he took the burger around to be photographed with different stars. Either way, the burger met more famous people that evening than most people will in a lifetime.

12 Awkward Musicians At Vanity Fair Oscar Party

Stevie Nicks, Lady Gaga, and Steven Tyler all sharing one single cushion at Vanity Fair’s West Hollywood Oscar Party 2014 is quite the sight. Thankfully, this photo captures an amazing moment. Nicks looks fantastic—her glasses allow her to emit the confidence we expect from her. Gaga and Tyler, however, are forced to fight their eyelids. Tyler’s an old vet. He’s allowed his eyelids to win the fight and embraces the moment, half alive but happy.

Gaga is using all her strength to keep those eyes open and straight. The result makes it appear that she’s hexing the photographer.

In the second photo, Tyler has given up the fight and just gone to sleep. Gaga, thinking that he’s doing a dramatic pose, takes the moment to look ferocious. She’ll have to settle for looking foolish.

11 Eddie Redmayne Turned Away By Rihanna

After the Met Gala in 2017, Rihanna threw an exclusive bash at the club, 1OAK. The party featured many of Hollywood’s elite as well as a number of incredibly famous musicians and stars of all sorts. Sadly, when Eddie Redmayne and his wife, Hannah Bagshawe, tried to get in, they were denied.

According to the The Daily Mail, the club was at capacity, which is why the stars were turned down, but that excuse rarely works for superstars.

Most security guards will not stop short of carrying out a few normal people with their bare hands to make room for a celebrity, but, apparently, Redmayne is not the right kind of superstar for Rihanna. After this denial, we highly doubt that Redmayne will be appearing in Battleship 2 or whatever awful movie Rihanna is in next.

10 Christina Ricci at Jean-Charles de Castelbajac’s After Party

After Jean-Charles de Castelbajac’s Ready to Wear show, Christina Ricci, who was in Paris filming Bel Ami, visited the exclusive after party to have some fun. Well, it appears she had a whole lot of fun. The actress was snapped many times throughout the night, few captured her with her eyes open.

Listen, we’re not here to judge. But, when you go out with Lindsay Lohan to a club and you come out of the night looking like the one who is worse for wear, questions will be asked. Ricci and Lohan went into the club looking incredible, but Ricci came out barely conscious. What’s important is that they had fun, and, judging by the photos of the dancing and the spilling, fun was certainly one of the party guests.

9 Bianca Jagger’s Horse

Bianca Jagger riding a beautiful white horse inside Studio 54 is one of those strange and magnificent photos that many people have seen, but not everyone is aware of the context. Well, it was Jagger’s birthday that night. Her then-husband, Mick Jagger, and the club owner decided to surprise Bianca with a horse much like the one she had. So, Bianca jumped on and walked around the club as people snapped photos.

According to the Financial Times, Jagger didn’t enter the club on horseback, a distinction the animal rights activist felt important to make. She simply got on a horse that was already there. Perhaps the strangest thing about the photo is what is going on in front of the horse. Off camera, is an unclothed man covered in gold glitter leading the horse. We don’t know why.

8 Sinatra And Farrow Escaping Capote’s Ball

Truman Capote’s Black & White Ball in 1966 is sometimes called the party of the century. It was a collection of the nation’s biggest stars in almost every field. While certain stories of awkwardness are told, such as Tallulah Bankhead insulting Norman Mailer, only one, it seems, is captured in a photograph.

According to the LA Times, Mia Farrow and Frank Sinatra weren’t having a great time at the masked ball. Sinatra is said to have felt silly in his mask and Farrow wanted to leave early. When they tried to escape the party, however, Capote wouldn’t let them. In fact, he stood in front of the doors not allowing them to exit. This photo appears to catch the moment that the couple slipped away, hoping not to be noticed.

7 Elton John’s 50th Birthday

If any other celebrity tried to wear this outfit, they would be exiled to an island for the rest of their lives. Elton John, somehow, gets away with it. Now, this was his 50th birthday, so we will forgive him his trespasses, but sweet lord, that’s a lot of material. Though technically a costume (Louis XVI), John’s outfit is much more likely to a fashion statement.

According to The Telegraph, the elaborate and extravagant costumes worn by John and his partner, David Furnish, also came with scantily clad servant men who carried John’s train all evening. Upon arrival, John and his posse exited the back of an enormous moving truck. It seemed that, while looking fabulous, John struggled to move under the sheer weight of the material.

6 Brooke Shields at Studio 54

Seeing pictures of Brooke Shields dancing up a storm at Studio 54 is amazing. It’s strange, to be sure, but it’s a great piece of pop culture history. Now, aside from the questionable dance moves, the big question here is: how old is Shields in these photos? Well, she’s only about 13. That’s right, times have changed. What was a 13-year old doing in a club that was so famous for its crazy parties?

To hear Shields tell it, she was invited often to these types of things, but she never got crazy. According to the Daily Mail, Shield said, “I would get invited to Studio 54, but I’d leave before all the craziness and […] happened. I never saw the bag passed around.” While Shields may have stayed out of trouble, many other young people at this club did not.

5 Drew Barrymore At Studio 54

By now, most pop culture fans know that Drew Barrymore was a bit of a wild child. She had a very unorthodox upbringing and became a celebrity very early in life. She got involved with the wrong people and the wrong substances far too early, and it led her down a difficult path. Still, she came out of it as an incredible person by all accounts.

That doesn’t make this photo of Barrymore at eight any less strange. This is Studio 54 and this is a child. In an interview with Today, Barrymore spoke about her own children and how their lives will differ from their mom’s. “And in the younger years, like, they’re not gonna have my life, you know,” she said. “Not going to Studio 54 at 7 years old will probably make them a lot more normal than I was.”

4 Katy Perry With Elephant

The gossiper, Perez Hilton’s, birthday party in 2010 was one for the ages. Many stars from many different eras made the guest list and some of the theatrics of the night are still discussed, if only by PETA and other animal rights activists. During that night, Perry made her entrance on the back of an elephant.

It sounds far-fetched and a bit over-the-top for a birthday party, doesn’t it? Well, it’s true. Looking back, the whole thing is awkward.

You see, Perry didn’t just come to the party as a guest. According to Sify, she was a performer. She came in costume, on an elephant, and came singing a song. Sure, if you were there, it was probably a real treat seeing a circus-like performance from one of the biggest musicians at the time. In 2018, it’s a bit cringe-worthy. Even circuses banned the use of elephants.

3 Ryan Kwanten Denied By Clooney

After the Oscars, picking the right after party is essential. Stars line up their plans for the evening early to avoid any embarrassing encounters. Sometimes, however, stars leave their planning to the last minute or they just fly by the seat of their pants. According to The Daily Mail, this strategy led to a bit of awkwardness for True Blood star, Ryan Kwanten.

When Kwanten and his handler tried to get into George Clooney’s exclusive party at Craig’s restaurant in West Hollywood, they tried to get the bouncers on the phone with someone who could mediate the situation. The security wasn’t having it, though, and Kwanten left visibly aggravated. Earlier that night, Kwanten attended Elton John’s party, which he clearly never should have left.

2 Chris Brown Carried Out

Going only by the pictures of the aftermath, BET afterparties get pretty crazy. We shouldn’t be shocked to see stars leaving these events a bit wobbly after an evening of partying, but, sometimes, we are. We are especially surprised to see grown men being carried out of parties because they seem incapable of walking on their own feet and legs.

This is Chris Brown, best known for things other than his music. Captured by TMZ, Brown was spotted being leaving a club on rubber legs, arms draped over his security. When he awoke to fans and cameras flashing, Brown decided to try and walk on his own. Still, his security helped him over to his car, in which he slumped drunkenly in the passenger seat. Thankfully, Brown had a driver waiting for him.

1 Milo Ventimiglia Goes Swimming

When Milo Ventimiglia went to the HBO Golden Globes after party, he didn’t plan on swimming. When he got there, swimming still didn’t make his to-do list, but that doesn’t mean he didn’t partake. After the Golden Globes, Ventimiglia posted a video to Instagram later in the evening congratulating the evening’s winners, some of who were his friends and co-stars.

Before signing off, the wet-headed Ventimiglia then admitted, “And yes, I fell in the pool.” For many, this was the final piece to the puzzle. According to E! Online, there was a buzz circulating that some silly goose fell into the Beverly Hilton pool during the after party. Ventimiglia felt no shame (ok, a little shame) in admitting that it was him. His sharing of the story turned an embarrassing moment into a hilarious one.

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