Prom Night: Throwback Pictures Of Celebs Dressed To The Nines (And Some Lookin’ A Fool) At Prom

April 30, 2013  |  
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Within the next month or so (or maybe the prom race has already started for the teenagers in your neck of the woods), most high school juniors and seniors will trade in their uniforms and overpriced sneakers to play dress up for a night. That’s right, it’s prom season. We’ve all got our memories from trying to match our ensembles with our dates, kicking off heels we couldn’t walk in to jam on the dance floor, going to the most popular (but cheapest) restaurants in town to eat with friends, and sitting in nail salons and hair salons for hours trying to get our french rolls right and tight. Before they were famous, celebrities were out here doing the same exact thing for their big night. It’s just a bit more entertaining to look back at their prom night photos. So why don’t we do just that?

Questlove and Amel Larrieux

Before he was producing for big names like D’Angelo and Jay-Z, and way before that fro caught major air, Questlove was just Ahmir Thompson, and he was just another talented student at the talent-filled Philadelphia High School for the Creative and Performing Arts. His classmates included everybody from Boyz II Men, to Questlove’s bandmate, Black Thought, and of course, Amel Larrieux, whom he called “The finest girl in school.” He asked her way before school started for senior year to be his date, because he knew his classmates would be thirsty, and obviously, she said yes.

Kerry Washington

Way before she was Olivia Pope on Scandal, Kerry Washington went to prom rocking a dress of her own design. No scandalous cut-outs or exposed belly buttons for her though! Washington had a beaded red babydoll gown created and rocked it with pearls…and a jean jacket. In her When I Was 17 episode, she said that her attempt to be different and wear a jean jacket with her dress angered her mom, so much so that they got in a huge argument on her big night. Ah well…she still looked cute, right?

Keri Hilson

In her gold shimmery dress with her hair looking absolutely fabulous, singer Keri Hilson went to prom with her boyfriend at the time, and clearly the pair was a cute one. However, according to Keri and her good friend Charlett, this same boyfriend would go on and cheat on her because Hilson says she wouldn’t do things his other chick would (she was a virgin throughout high school). But I’m sure he’s somewhere salty now, wishing he could freeload off her success. Too late! She has a much finer man now in Oklahoma City Thunder baller, Serge Ibaka.

Trey Songz

He might be able to sing a few people’s panties off these days, but at first glance with his above prom photo, Trey Songz would have received a haughty laugh in the face if he stepped to a chick talking about “I Invented Sex.” Despite this very regrettable hairstyle, the singer was attending barber school and used his talents to not only cut the hair of his friends, but to do the eyebrows of his date for their big night. That’s all good and dandy, but I’m still very upset by this picture…


As we all know, by the time it was actually time for Aaliyah to go to prom, she had actually been in the industry and doing very well for a while, signing her first record deal at 12. But despite all that, she took some time out to go to prom with her friends at Detroit’s High School for the Fine and Performing Arts, where she picked up her high school diploma. Here’s what she told People about her prom experience, which took place back in ’97, a year after One in a Million dropped.

“I took four of my friends—two girls and two guys. I didn’t have a boyfriend, so I thought I’d enjoy myself more if I went with a group of people.”

But that wasn’t the only reason Aaliyah stood out at her prom.

“I didn’t want to wear a dress. I wanted to be different, so I wore pants. It was a white-lace outfit that I bought in August of ’96. I saved it for the prom… My girlfriends wore white pantsuits, and the guys wore black suits. I had it coordinated. It was kinda fly.”

Of course, the man in the photo above is clearly not her date, but this is what homegirl looked like in her white lace outfit on her big night. Always different, always fly!

Busta Rhymes

Clearly these two were having, or were going to have, a VERY good night. As Yvette would say in Baby Boy, “It’s all in ya grill…”

Bussa Buss and his date were very chic in their attire, which included a bold bow tie, a sheer and lace dress, a mean bang, and some growing locs. This was way before he was clowning in some of his iconic music videos. And despite him looking crazy as a fox in the picture above, these two were definitely a sharp duo.

Taye Diggs

There are many women out here who find Taye Diggs (far left) to be absolutely delicious. I was very much part of that group back when How Stella Got Her Groove Back was released (though that Jamaican accent was a bit tired), but this photo just rips all that sex appeal away, like a rug being pulled from under you. Of course he still looks good, but we’d like an explanation for these glasses. And no, “It’s the ’90s” will not suffice! Blame it on being a theater geek…

La La Anthony

Two proms are better than one! Former MTV VJ and current reality personality and real-life basketball wife La La Anthony had a thing for light beige-ish/champagne, because she opted for such light colors for her prom dresses for both years. She also clearly had an appreciation for pointed-toe heels. And if you didn’t believe her bond with her cousin Dice was oh so tight, you can see the two in the photo below heading out to prom with their girlfriends. Cute! And we see you looking fab with the flip Dice!

Pauly D and Snooki of Jersey Shore

Before he made the decision to have his hair standing up on his head and when she was just a tiny cheerleader and not a well-known party girl, they were both just regular high school students trying to be cute at prom. I think we can all agree that their looks were a whole lot more tame than they wound up being later in life…And yes, Pauly D was still looking good, even with those Michael Jordan hoop earrings in both ears.

Danielle Fishel and Lance Bass From ‘N Sync

If you missed the slideshow from last week about gay men and the women who date and marry them, this might be news to you. At the time these two went to prom together (her prom), Fishel was a big star from playing Topanga on Boy Meets World and Bass was a huge star thanks to his part as a lip-synching member of ‘N Sync. Back in ’99 she asked him to come to her prom when they were dating, and he said no. Only because he was scheduled to be in Japan. But luckily for her, his plans changed and she told US that he sent her three dozen roses and said, “‘Plans have changed, I’ll be in town. Can I take you to prom? Check yes or no.’ And there were two little boxes! So, of course, I checked the box yes.”

Brandy And Kobe Bryant

Who didn’t wish these two actually turned into a couple after their cute prom date? Looking absolutely adorable, Brandy to this day can still recount how Kobe asked her to be his date, and how the experience was one a famous pop star like herself needed to stay grounded:

“When I was 17, I didn’t get a chance to go to my own prom but that same year I was at an Essence event and this tall good looking guy comes up to me and goes “Oh my god, I’m a big fan of yours, you should go with me to prom.” ‘Dude, first of all like, who are you?’  We went through a whole resume. “I’m the number one high school basketball player in the world, my name is Kobe Bryant”. I still didn’t know who he was because [back] then I didn’t know much about basketball. I knew who Michael Jordan was but that was about it.”

“We were dancing; it just felt real. I needed that..I really needed to experience that and I wouldn’t if Kobe never asked me.”

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