20 Horribly Awkward Prom Photos

Highschool is a very awkward time to be alive.  We are growing into out bodies, and learning how to be a social human.  Have you ever gone back and looked at your cringeworthy prom photo from many years ago?  Well, these are the worst of the worst!  Enjoy!


Class Act Michelle Obama Caught in Wicked Chair


Whoever thought that wicker would be great for a formal prom photo that would stick around for decades did not have two cents to rub together in the common sense category. Does Michelle look angry in this pic to you? Who can blame her?

Who Spiked the Wolf?


Taylor Lautner may still look sexy in this prom pic, but we have to wonder what’s up with those spikes. For his date’s sake, Taylor should have put safety tips on those bad boys. Hopefully, he didn’t get too close to the celebratory balloons.

Is Brad Pitt Acosting His Date?


Brad Pitt appears to be holding his date in place in this incredibly overstaged promshell pic. The lighting is so bright that the main features are his date’s dark roots and Brad’s conspicuously not-blonde bowl cut. Let her go, Brad, you have a bright future with lots of lovely ladies.

Courteney Cox was No Fox


This beautiful star could not look more dowdy in this course photo. Although she is smiling, the stiff backbone of Cox and her date give away their discomfort. This is one of those photos you hide away in a drawer and prayer no one ever sees again. But we have brought it out into the light. No, no…put it back.

Not-yet Fergalicious


Fergie might be the queen of self-taught sexy, but she didn’t start out that way. While the star emits a certain country buxomness, her eraser head date ruins the affect.

Bad Hair (Can You Believe It?) Prom Night for Jennifer Aniston


Jennifer Aniston stands proud in a lovely sweetheart black velvet dress and bright smile. Too bad her hair looks like she forgot to brush it. Even for ’80s bad hair wear, this stands out as further proof that beauty is not born, but cultivated. It’s okay, Jen, we still respect you.

Snooki Attacked By Date’s Boutineer


Tanned seems to have come unnaturally to Snooki at a young age. The reality star looks happy and toned down in this photo, even though she looks like she is being attacked by her date’s boutineer.

Christine Aguilar Before Her Chest Got Its Own Zip Code


Christine Aguilar sports her signature platinum locks in this prom pic. However, her profile exhibits a far more natural silhouette without the hooters she bought later. Maybe it’s time to downsize the silicone, Christine. Just saying.

Will Ferrell is Queen of the Ball


Will Ferrell looks lovely in a tiara in this high school formal portrait. In other versions, his date sports a markered in beard and glasses. ‘Nuff said. We bow to the king of comedy.

Barack Obama Looks Like the Creature from the Black Lagoon


It’s hard to believe this silly youngster later nabbed a hottie like Michelle and became the leader of the free world. Wonder what the prom theme was – Under the Swamp? Good thing you’re cute, Barack.

Jessica Alba Goes to Prom as French Waitress


Jessica Alba was trying way too hard in this get up that is NOT age appropriate. I want to reach back in time and tell her get paid before dressing up as a sex fantasy. Although, this is admittedly great prep for her later Sin City performance. OK, Jessica, you make that outfit work – but I am jealous so poo on you!

Lady Gaga Stag at Prom


It appears Gaga had no monster following at the time this pic was taken. She is posed with similarly dressed teens in a group photo. Did she go to her prom stag? Rumor has it, well, we couldn’t figure it out. However, she reputedly arrived in a real pumpkin.

Natalie Portman Looking Like an Old Lady at her High School Formal


Lovely Natalie Portman undoubtedly has stylists to help her further her posh image as an extraordinarily intelligence and talented star. However, in this particular case, Natalie either went way-wrong vintage or let her not-hip grandmother dress her. Just, yuck to the dress, Nat. The skirt doesn’t match, and, girlfriend, can we talk about those tan lines?

Lance Bass (and Topanga)


Lance Bass is a producer and actor in his own right. However, all we see here is Bass trying to grab some (Topanga) – well, you know what we mean.

Ru Paul Spikes are Bigger than Taylor Lautner’s


Ru Paul is characteristically androgenous in her/his prom photo. Looking tall and dashing enough to get a dreamy-eyed gaze from his date, this trendsetter exhibits the raw flair that made him/her famous.

Why Does Tupac Look Like He Knows Something We Don’t


Tupac Shakur had a brief life, dying violently at 25, but he spread around enough swagger to turn heads even today. Perhaps he is already plotting his wildly successful wrap career in this staged pic that he completely owns.

Who Dat Dog?


Dred Dogg meet prom dog. Yep, this is none other than Snoop Doggy posing as a prom prince. Wow, wonder how long it took his hair to grow in.

Oh Myyy, Miley!


This post-Hannah Montana pic shows a softer side of the star, but I don’t think we’ll find it in her portfolio.

Jaden Smith


This photo of Will and Jada’s mini is too adorable to poke fun at. Is that a storm trooper outfit? (Said lovingly.)