30 Of The Most Awkward Celebrity Prom Photos Of All Time

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Credit: Instagram @bradpittofficial[/caption] Somewhere there's a grainy picture of me in a dinner jacket and bow-tie holding a glass of prosecco ready to go to my sixth-form ball (that's what we call "prom" here in England), stood on my own because I didn't have a date and barely concealing a deep sadness behind my eyes. These days, I'm pretty happy with how my life has turned out, but every time I stumble across that picture I feel a hot shame and embarrassment at the memory of how awkward my teenage self was. These 30 celebs have more reason than most to feel pretty good about how their lives turned out, but I bet more than a few of them still look at these old prom photos and find that they have to hide behind their hands for a little while until the embarrassment has passed. Let's dive in and see who put in the best efforts when it came to making themselves look glamourous for prom, and who's aged the best since then. [post_page_title]Jeremy Renner[/post_page_title] Ten out of ten for little teenage Jeremy. He's scrubbed up very well in a natty, shiny white suit and has gone to town with the accessories, adding a fancy floral buttonhole and a matching pink bow-tie and hankie. I won't even start talking about how spectacular his mullet is, because once I start I'll never stop. [caption id="attachment_3955" align="aligncenter" width="800"]

Credit: Twitter @Renner4Real[/caption] Now - Jeremy's ditched the mullet and is bit more rugged and manly now, and he's traded in his fancy white suit for a bow-and-arrow as everybody's least favorite Avenger. He was also maybe in one of the Jason Bourne movies (the one that didn't have Jason Bourne in it, I think?) and owns an app where people pay him money to receive compliments from him. Overall, I can't deny that I prefer awkward teenage Jeremy over his adult self, so Prom Renner wins this one.

[post_page_title]RuPaul[/post_page_title] Gotta say, teenage RuPaul seems to have none of the cringe-worthy awkwardness of most prom-bound teenagers and looks pretty formidable and self-assured. Not sure if that's a giant safety pin he's adorned his jacket with, but he's also incorporated leather fingerless gloves and shiny stripy trousers, so his tendency for looking fantastic has settled in early. [caption id="attachment_3956" align="aligncenter" width="800"]

Credit: Twitter @RuPaul[/caption] Now, as wonderful as teenage RuPaul looks, there's a formidable steely glare there that would've made me quake in my prom shoes when I was a teenager. These days RuPaul's a much warmer and more fun presence on

Drag Race

and has only taken his fashion choices to even greater heights, so adult RuPaul wins this on.

[post_page_title]Barack Obama[/post_page_title] I reckon Adult Obama can look back on this one and be pretty happy. He's already got his megawatt smile and has an impressive head of hair that's sadly deserted him over the years. He's also showing some creativity in his prom outfit by accessorising an ordinary white suit with a fetching necklace of leaves, as you do. [caption id="attachment_3957" align="aligncenter" width="800"]

Credit: Instagram @barackobama[/caption] Now, hair aside, Obama honestly looks more or less exactly the same as he did back then and has aged ridiculously well. He seems to have abandoned his fondness for dressing up in foliage but he also became the leader of the free world and inspired a few million people, so we've got to call it a draw on this one.

[post_page_title]Will Ferrell[/post_page_title] Teen Will Ferrell's prom pic is so ridiculously awkward it almost looks deliberate. He's stolen his date's tiara and put it on his own head, which only serves to highlight how massive his head is. He's also got a look in his eyes which half looks like nervous embarrassment and half like he's going to murder someone. Really astonishing stuff. [caption id="attachment_3958" align="aligncenter" width="800"]

Credit: Instagram @celeb.prom.pics[/caption] Over the years, Will Ferrell's doubled down on the goofy instincts that led him to steal some poor woman's tiara and built a whole career out of being an absolute idiot. It's also very rare that he stares into a camera in a way that makes you fear for your life, so I reckon adult Will has made improvements over his teenage self.

[post_page_title]Angelina Jolie[/post_page_title] I think teen Angelina's done very well here, actually. She's accessorized with some sort of necklace which looks like a piece of treasure from a Tomb Raider game, so she's cleverly anticipated her own career in her outfit choices. She looks a tiny bit like she can't be bothered to be there, but overall I think she can look back on this without too much embarrassment. [caption id="attachment_3960" align="aligncenter" width="800"]

Credit: Reddit @lovinglogs[/caption] Now, Angelina's ability to predict her own future seems to have fallen by the wayside in recent years, as I can't remember the last time I saw her wearing anything that predicted a future role in such a way as she achieved at prom. For losing her magical powers of foresight, I've got to hand this one to teen Angelina.

[post_page_title]Terry Crews[/post_page_title] Either Terry Crews' teenage home actually resembled a studio for a catalog photo shoot, complete with candlesticks that complimented the color scheme of his and his date's outfits, or he put so much effort into his prom that it overcomes how scared he seems to be of the camera and how little he wants to be there. [caption id="attachment_3961" align="aligncenter" width="800"]

Credit: Twitter @terrycrews[/caption] Now, I'll be honest, I can't imagine legendary tough-guy adult Terry finding the time to go to the shops and buy some nice pink candles and a silver candlestick to act as set-dressing for his prom photoshoot. He may have become more comfortable in front of the camera, but for the sheer sweetness of the photo, I'm going to let teenage Terry win this one.

[post_page_title]Ellen DeGeneres[/post_page_title] Now look, I know that before the rise of digital photography you couldn't have endless attempts at the same photo, but surely Ellen could've got a prom photo where she's not actively grimacing at the camera? Also, why she decided to take the picture in front of what looks like an enormous cartoon duck is another mystifying choice. [caption id="attachment_3963" align="aligncenter" width="800"]

Credit: Instagram @edbyellen[/caption] Now, I must confess to largely being aware of Ellen DeGeneres thanks to her wonderful performances as Dory in

Finding Nemo

and its sequel, Finding Dory. As such, I've no idea if she's still in the habit of being photographed in front of cartoon ducks with guys who can't be bothered to take their hands out of their pockets, but her performance is so full of joy that I can't imagine her being caught scowling like this again. I'm handing this one to adult Ellen.

[post_page_title]Lady Gaga[/post_page_title] Is she the one in the middle? In light blue? I THINK she is. It's hard to tell because Lady Gaga has significantly dialed up the wow factor of her outfits since then. But she's done pretty well in her prom photo, I think. She's got the biggest corsage (the girl on her left hasn't even got one!) and the biggest earrings. A solid effort. [caption id="attachment_3964" align="aligncenter" width="800"]

lovely

Credit: Instagram @ladygaga[/caption] Now, at some point since this photo was taken, Lady Gaga must have thought, "It's not enough for me to be able to stand in a row with my friends and look nice alongside them, I must make sure that nobody looks at anybody other than me EVER again!" hence her tendency to wear dresses made of meat and so on. It certainly worked when it came to winning her lots of attention, so good on her. Adult Gaga wins this one.

[post_page_title]Sandra Bullock[/post_page_title] Oh now, this is just a

lovely

photo. If I had a photo of me at my prom that was as lovely as this, I'd never feel embarrassed about my teenage self at all, I'd just think, "Wow, look how happy and in love I was at my prom!" I think there's a slightly dubious weird pigtail thing at the back there which maybe she'd do differently these days, but it barely matters with a photo this lovely. [caption id="attachment_3965" align="aligncenter" width="800"]

Credit: Instagram @celeb.prom.pics[/caption] Now, I don't think she's bundled her hair up into a weird pigtail for a while, and she's also won an Oscar, so I doubt she looks back on this photo and thinks, "Wow, my life peaked there." But I stand by it - this photo is adorable, and if it was a photo of me I'd struggle to ever get over it. I'm giving this one to teenage Sandra.

[post_page_title]Jimmy Fallon[/post_page_title] I don't know if Jimmy Fallon and his date was deliberately going for an Addams Family/Tim Burton vibe here, or if it happened by accident, but certainly somewhere between the pale face, the crooked bow-tie, his date's crazy hair, and the decidedly odd positioning, there's a real "They're creepy and they're kooky, mysterious and spooky" vibe to this one. [caption id="attachment_3978" align="aligncenter" width="800"]

Credit: Twitter @jimmyfallon[/caption] Well, I've got to be very honest and say that Jimmy Fallon has certainly aged into his features quite well and looks decidedly less awkward than he does in this photo. But, quite honestly, I kind of like the Addams Family and Tim Burton, and I think the awkward kookiness of this photo is funnier than a lot of Fallon's skits these days, so I think teenage Jimmy wins this one.

[post_page_title]Jennifer Aniston[/post_page_title] I think Jen's managed to emerge from prom with a lot of class intact, actually. The big 80s hair is very much a product of its time, but for someone who created one of the defining haircuts of the 90s we should expect nothing less. I think this is a solid entry. [caption id="attachment_3981" align="aligncenter" width="800"]

Credit: Reddit @I_dont_like_pie[/caption] Besides that hair, it's difficult to identify that many ways in which Jennifer Aniston has changed significantly from her teenage self - she already looks pretty confident and collected and can look back on this one with pride. Still, the fact that in this photo she's yet to have had 90% of the population trying to copy her hairstyle means adult Jen probably wins out overall.

[post_page_title]Jessica Alba[/post_page_title] I've got to be honest, teenage Jessica's choice of outfit is a bit weird. She looks lovely and happy and smiley and seems to be having a great time, but her dress has little balls of wool dotted all over the front of it that reminds me of a blanket my mum once knitted that was supposed to represent a field and had little balls of wool as the sheep, and I think that's a weird thing to wear to prom. [caption id="attachment_3983" align="aligncenter" width="800"]

Credit: Instagram @jessicaalba[/caption] Again, all the confidence and class of adult Jessica seems to already be in place in her prom photo, but she's stopped wearing things that are likely to make people say, "Why are there little balls of wool all down your tummy, are they supposed to be sheep or something?" so let's chalk this up as a win for Adult Jessica.

[post_page_title]Matthew McConaughey[/post_page_title] I refuse to believe that Matthew McConaughey is old enough to go to prom in this photo. This seems to be a photo of an eight-year-old boy standing on his friend's shoulders and hiding inside a tux and barely believing his luck that nobody seems to have called him out on it yet. [caption id="attachment_3986" align="aligncenter" width="800"]

was

Credit: Twitter @leahkpickett[/caption] Whether or not Teenage Matthew really

was

an eight-year-old boy getting away with pretending to be older than he was, or if he just aged into his face a solid decade later than you'd imagine, I don't think any of us can deny that Adult Matthew looks less ridiculously out-of-place when trying to pass himself off as a grown-up these days, so teenage/little boy Matthew loses this one.

[post_page_title]Bruce Willis[/post_page_title] I was under the impression that Bruce Willis was in his 60s, but I guess I was wrong because here we have a photo of him going to prom which seems to have been taken in the late 1800s, which would make him about 150 years old. This would explain why he's seemed so tired in a lot of his recent movies. [caption id="attachment_3987" align="aligncenter" width="800"]

Credit - Instagram @celeb.prom.pics[/caption] Look, I'm not going to deny that teenage Bruce, with his fancy suit and a full head of hair, scrubs up a bit better than adult Bruce. But that's only to be expected for a guy over who's over 150 years old, so let's give him a break and pretend that adult Bruce wins it.

[post_page_title]Brad Pitt[/post_page_title] Now look, Brad's tried very hard and brushed his hair neatly and is doing his best to flash a nice smile even though his eyes look like the tired eyes of a man who's been in prison for a decade, but his tie's wonky and his jacket's a different color to his trousers. A middling effort from teenage Brad. [caption id="attachment_3988" align="aligncenter" width="800"]

Credit: Instagram @bradpittofficial[/caption] Now, I've seen Adult Brad wear a proper dinner jacket in multiple

Ocean's

movies, so the fact that he couldn't scrub one together for prom is a bit disappointing. For having consistently put in more effort since this photo was taken, adult Brad wins this one easily.

[post_page_title]Robin Wright[/post_page_title] I'm not going to deny that teenage Robin doesn't look incredible here, but she does seem to have hired a professional studio for her prom shoot and even worn a crown for it to make it so obvious how great she looks. So I've got to deduct some points for her extreme overconfidence here. [caption id="attachment_3989" align="aligncenter" width="800"]

Credit: Instagram @robingwright[/caption] I think adult Robin has aged very well since this photo and still looks just as great, but what makes her performances in films like

Forrest Gump

and

The Princess Bride

so brilliant is her down-to-earth warmth and humanity, so I'm going to let adult Robin take the crown from her teenage self here.

[post_page_title]Taylor Swift[/post_page_title] Look, no offense to Taylor Swift's date, but I would say the main thing that adult Taylor might look back on and cringe at is how embarrassed she seems to look at having to stand next to this guy with the backward cap doing gangster hand gestures. Taylor herself looks great, but she seems aware that the company she's keeping here maybe isn't the best. [caption id="attachment_3990" align="aligncenter" width="800"]

Credit: Instagram @taylorswift[/caption] Adult Taylor has obviously gone from strength to strength and keeps better company now in partner Joe Alwyn, but the real question is: what happened to her date? Did he stop wearing such dated headgear? Did he start doing less embarrassing things with his hands? I bet he did, and I hope he's happy and successful and I wish him the best. Adult Taylor wins this.

[post_page_title]Reese Witherspoon[/post_page_title] This is really weird. Teenage Reese looks a LOT like my sister in this one, so I'm finding it hard to look at this picture and find anything other than a sort of familial, brotherly fondness for her. Like Bruce Willis, it's a little odd that it seems this picture was taken a good thirty years earlier than you'd expect, but I think she looks great. [caption id="attachment_3991" align="aligncenter" width="800"]

Credit: Instagram @reesewitherspoon[/caption] Now, I think this one's too close to call. I think teenage Reese looks classy and confident, and I think adult Reese also looks great and has had an impressive career, so it's hard to say which one is the real winner. I suppose it has to be adult Reese, because when this photo was taken the

Legally Blonde

movies didn't exist yet, and we've got to hand it to her for making those.

[post_page_title]George Clooney[/post_page_title] Don't wanna be too mean to teenage George, but I've got to say that he comes across as a bit of a sleazeball here. Those heavy-lidded eyes look a bit leery, like a lizard, and those shiny reflective lapels would make me think he was up to no good. A good head of hair, though. [caption id="attachment_3992" align="aligncenter" width="800"]

Credit: Instagram @celeb.prom.pics[/caption] Now, adult George strikes me as an absolute gentleman. No longer prone to being photographed with an expression that makes you think he's imagining what you look like naked, and less given to wearing metallic suits. Adult George wins by a mile for being less creepy than his teenage self.

[post_page_title]Rihanna[/post_page_title] A mostly impressive showing from teenage Rihanna and her date here. She seems to be having a good time; he seems a bit bored but basically fine, and they've both dressed up nicely. The only thing dating this photo to any extent is that both their haircuts are so ridiculously defined that you can imagine somebody drew them onto their heads with felt tip pen. [caption id="attachment_3993" align="aligncenter" width="800"]

Credit: Instagram @badgalriri[/caption] Now, Rihanna's hair these days looks less like it was frozen onto her head, so I'm giving this to adult Rihanna.

[post_page_title]Michelle Obama[/post_page_title] This is spectacular. It's like an album cover. It's so well co-ordinated. Her outfit matches the chair AND the decorations on the table! That's some Terry Crews-level set dressing right there. I imagine this would be an album of classic love duets, and I'd buy it. [caption id="attachment_3994" align="aligncenter" width="800"]

Credit: Instagram @michelleobama[/caption] I love this photo so much that I really want to just hand this one to teenage Michelle without any contest whatsoever, except the one thing that makes me think adult Michelle might have the edge is the idea of her doing a follow-up album of more love duets but with Barack as her partner in place of her prom date. That'd be an absolute chart-topper. Let's call it a draw.

[post_page_title]Beyoncé[/post_page_title] A mostly stunning prom entry from teenage

Beyoncé here. Although I have to deduct some points for those weird holes in her dress around her waist, which look a bit like someone's attacked her with a giant hole-punch. An odd decision. [caption id="attachment_3995" align="aligncenter" width="800"]

Credit: Instagram @beyonce[/caption] Now, I wouldn't care if Beyoncé's prom photo was the most incredible, stunning, brilliant photo ever taken, adult

Beyoncé is a legend and for all her great work easily triumphs over her teenage self, no questions asked.

[post_page_title]Scarlett Johansson[/post_page_title] Look, I love Scarlett Johansson as much as the next guy, but she seems to have gone to prom wearing a shirt. This is madness. She seems pretty confident about it though. Her look seems to be saying, "Yeah I'm just wearing a shirt. Wanna fight about it?" so extra points for sass. [caption id="attachment_3996" align="aligncenter" width="800"]

Credit: Twitter @PageSix[/caption] Teenage Scarlett's confidence and sass are still intact, and do you know what? Her filmography's impressive enough that she can go to prom in whatever she wants. All kudos to teenage Scarlett for living her truth and wearing whatever the hell she wanted. She can win this one.

[post_page_title]Ashton Kutcher[/post_page_title] I take no issue with teenage Ashton's wardrobe choices. He looks good. The scraped-back hair is a bold choice, but hey, your teenage years are all about bold choices. I've no idea what dance moves he's demonstrating here, but the slightly strained smiles of the women behind him suggest they are perhaps acceptable at best. [caption id="attachment_3997" align="aligncenter" width="800"]

Credit: Instagram @aplusk[/caption] Now, adult Ashton seems a little more relaxed and comfortable in his skin than teenage Ashton, and less prone to launching into an impromptu dance routine with so much enthusiasm that it makes the people around him slightly uncomfortable, so adult Ashton takes this one.

[post_page_title]Natalie Portman[/post_page_title] Teenage Natalie's outfit is great, but the slightly flyaway hairdo and nervous, rabbit-in-headlights stare makes her look a tiny bit like a frightened young chicken, which diminishes the overall impact of her prom look. [caption id="attachment_3998" align="aligncenter" width="800"]

Credit: Instagram @natalieportman[/caption] Other than the Star Wars prequels, it's rare these days that we ever see adult Natalie seeming as uncomfortable in her surroundings as she seems in her prom photo, so adult Natalie is the victor here.

[post_page_title]Blake Lively[/post_page_title] Teenage Blake herself looks confident and great, so you'd think she'd look back on this photo without too much embarrassment. But why is her date so frightened to actually make physical contact with her shoulders? Does he know something about her we don't? Does she have corrosive skin? Why don't we know this about Blake Lively?

[caption id="attachment_4000" align="aligncenter" width="800"]

Credit: Instagram @blakelively[/caption] Whatever the explanation for this photo is, adult Blake seems to have the edge over teenage Blake. Either she's now able to hang out with people confident enough to actually make physical contact with her, or she's got the strange medical condition that caused her corrosive skin sorted out, so she's definitely the winner.

[post_page_title]Courteney Cox[/post_page_title] Teenage Courteney seems to have brought the biggest bouquet of flowers possible to prom. She's going to regret that later. She's going to be trying to dance and constantly being irritated by this massive great bouquet she has to wave around. Or she'll have to ask someone else to hold it while she dances. Poor planning. [caption id="attachment_4001" align="aligncenter" width="800"]

Credit: Instagram @courteneycoxofficial[/caption] Now, we can't imagine the woman who brought Monica Geller to life to go into an event as poorly-prepared as teenage Courteney seems to be here, swinging around a bouquet the size of her leg and generally making things difficult for herself. For her improved planning skills, adult Courteney wins.

[post_page_title]Shane Dawson[/post_page_title] I'm going to be completely honest, I've no idea who Shane Dawson is. He seems to be wearing a suit about ten times too big for him, and his hair is ridiculous. But you know what? He's owning it. Good on him. [caption id="attachment_4002" align="aligncenter" width="800"]

Credit: Instagram @shanedawson[/caption] As I said, I couldn't begin to tell you who Shane Dawson is, so who am I to judge on how his life has unfolded since his prom photo? But teenage Shane strikes me as a guy who makes bold choices and sticks to them, so I'm letting him have this one.

[post_page_title]Amy Poehler[/post_page_title] The fact that teenage Amy seems to have been caught, paparazzi-style, emerging from a car when she didn't know she was being photographed for her prom, suggests that she was already enough of a big deal in high school for desperate journalists to lie in wait trying to get candid snaps of her. So kudos to her for being a big deal at a young age. It's just a shame they seemed to catch her in the middle of chewing on some Haribo or something. [caption id="attachment_3999" align="aligncenter" width="800"]

Credit: Seth Poppel/Yearbook LibraryNow[/caption] Amy Poehler is another actor who I'm largely only familiar with thanks to her voice work in a Pixar film.

Inside Out

is one of the most incredible films of all time and I cry my eyes out every time I see it, so I'm going to let adult Amy win this one because that dream role is still in teenage Amy's future when this picture was taken.