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.
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.
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. Hours before her arrest, a few shots were snapped of Young with some of the biggest stars in Hollywood, including Angelina Jolie, Brad Pitt, and Sandra Bullock. It was reported that while Sean was leaving the LAPD Hollywood Substation, she had blamed the arrest on the Academy's lawyer. She also claimed that while she was waiting with friends to enter the Governors Ball, an Oscar official suggested security make a citizen's arrest. She never explained why the official made that suggestion, and she didn't mention any physical encounter with the security guard.
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?
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.
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.
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.
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.
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.
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.
When Eddie Redmayne Got Turned Away By Ri Ri
When RiRi decided to throw the after-party for the Met Gala in 2017, there were many elite guests of Hollywood on her list of invitees. Unfortunately for Eddi Redmayne and his wife, Hannah Bagshawe, when they tried to get in, they were denied at the door.
Apparently, the wife had reached full capacity....but does that excuse actually work for superstars? Many security guards would allow at least two people inside if the club is full.....and especially if they're celebrities. It looks like Redmayne was not the right kind of celebrity for Rihanna. Maybe next time Eddie!
Christina Ricci At Jean-Charles De Castelbahac's After Party
After Jean-Charles de Castelbajac's Ready to Wear show, Christina Ricci, who just so happened to be in Paris at the time filming, decided to head over to the party to get down. Well...it looks like she ended up having just that. A lot of fun.
Out of all of the photos taken of her that night, it looks like almost all of them are with her eyes closed. We guess that's what happens when Lohan takes you under your wing. Both Ricci and Lohan went into the club looking like dimes, but left looking almost barely alive.
Bianca Jagger's Horse
This is probably a strange photo many people have seen floating around the internet. It features Biana Jagger riding a beautiful white horse inside Studio 54. You're probably wondering, honestly, how did that photo even happen? Well, it was Jagger's birthday that night. (So obviously things are bound to get strange). Her husband at the time, THE Mick Jagger, along with the club owner, decided to surprise Bianca with a horse that resembled the one she had. So, naturally, Bianca jumps on and starts walking around the club while people snap photos of her.
The Financial Times, claims that she didn't enter the club on horseback, something that animal rights activists were making a point of. All she did was get on a horse that was provided to her in that moment. (As if that matters). One of the weirdest things about this photo is what is going on in front of the horse. We see an unclothed man covered in gold glitter leading the horse in question. We don't know the backstory behind that but seeing as it's the Jaggers, are we really that surprised?
Sinatra and Farrow Escaping Capote's Ball
The party of the century? Oh, you mean Truman Capote's Black & White Ball in 1966? This party had the nation's biggest stars in attendance in almost every field. It seems that there are a lot of awkward stories about this party that could be told through photographs, but this seems like one of the most important ones.
It's said that Mia Farrow and Frank Sinatra weren't having the best time at the party. Frank Sinatra claimed that he felt silly in his mask, and Farrow said she wanted to leave early. When they tried to leave the party, Capote insisted that they stay. He was so insistent in fact, that he stood in front of the doors so they couldn't leave. This photo captures the moment the couple tried slipping away hoping not to be noticed.
Elton John's 50th Birthday Party
If someone else tried to wear this outfit in public they would be roasted until they were nothing but burnt crisps. But obviously, Elton John isn't someone else. The party was to celebrate his 50th birthday, so obviously Elton John can do whatever he wants.
It was reported by The Telegraph that these costumes worn by John and David Furnish, came with servant man who were dressed in almost basically nothing who carried John's train all night. Honestly, Elton John looks like he knows how to throw a party!
Brooke Shields At Studio 54
These photos of Brook Shields getting down at Studio 54 are ICONIC. This is pop culture history in the making, and although these photos have been referenced for decades, they were also incredibly controversial. Brooke Shields was only 13-years old at this time... Which is obviously a quite young (and including illegal) age to be getting down and dirty at a club that was famous for it's insane parties.
The way Shields tells the story is that she were invited to these parties, but she would never actually get crazy. She said, "I would get invited to Studio 54, but I'd leave before all the craziness happened. I never saw the bag passed around." While it seems Shields was well-behaved at these parties, there were some younger ladies who definitely did NOT behave.
Drew Barrymore at Studio 54
If you're a big fan of pop culture and Hollywood itself, then you probably already know that Drew Barrymore was extremely wild. She became involved in celebrity culture at a very young age, and she got involved with the wrong people and the wrong substances early on. Regardless, through all her struggles, she emerged an incredible person an actress. Nonetheless, this picture of Barrymore at Studio 54 is still incredibly questionable.
When she speaks about how her children will be brought up she says, "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." If you're a big fan of pop culture and Hollywood itself, then you probably already know that Drew Barrymore was extremely wild.
Katy Perry With This Elephant
Perez Hilton, the famous gossiper had a birthday party back in 2010 that was certainly one for it's time. The guest list was made up of many different stars from many different eras, and many of the activities that occurred this night are still discussed, (especially by PETA).
It was on this night that Katy Perry made her entrance on the back of an elephant. The funny part was, Perry wasn't an actual guest...She was performing. Yes, she showed up in costume, on an elephant, and came in singing a song. If you were there it was probably incredible, but looking back on it now, it's all incredibly awkward. Even circuses have banned the use of elephants.
When Ryan Kwanten Got Denied By Clooney
The after-party after the Oscars is a pretty big deal. Many stars line up their event extremely to avoid any embarrassing encounters, (cough, cough, Eddie Redmayne). However, some stars just leave their planning until the last minute, or see if they can just make make a last minute party. It was reported that True Blood star, Ryan Kwanten, decided to leave his plans for last minute which led to an award encounter.
When Kwanten and his handler attempted get into George Clooney's party at Craig restaurant in West Hollywood, they told the bouncers to get on the phone with someone who could mediate the situation. Security still would not let them in, and so Kwanten left irritated. Earlier that night, Kwanten was seen at Elton John's party.....Looks like he probably shouldn't have left.
When Chris Brown Had To Be Carried Out
Judging by the photos above, BET parties can get pretty wild. After Chris Brown got his drank on at one of these said parties, TMZ captured him leaving the club on what seems to be baby deer legs.
He had both hands on his security guards since it seems he couldn't stand on his own. When he awoke to all the fans and flashing cameras, he tried to walk on his own. His security then helped him over to his car, and slumped him down in the passenger seat while his driver drove away.
Milo Ventimiglia Goes Swimming
