Rarely are photographs imprinted so heavily with the spirit of the times such as prom pictures. Perhaps the awkward hilarity of those photos decades later is proportional to the efforts graduating seniors invest in order to be as fashionable as possible for their big night. When the dates for the night have tried equally hard, the funny factor logically doubles. But such snaps are nevertheless a powerful monument to youth, a certain time, and to the speed with which it whizzes past.
Celebrities are, of course, not excluded. Especially as they were not celebrities, but only insecure kids at the time. Here are nineteen bittersweet photos of now-famous people and their dates snapped on prom night.
1. Brad Pitt
The Kickapoo High 1982 graduate from Missouri reportedly taught his sweetheart to dance to Michael Jackson’s Rock With You.
2. Matthew McConaughey
After the Texan won the Best Actor Oscar for Dallas Buyers Club in 2014, his prom date’s niece tweeted their portrait from the Longview High School bash in 1988 in Longview, Texas.
3. Kim Kardashian
It seems Kim Kardashian always knew how to get tongues rolling, as her prom date was none other than Michael Jackson’s nephew T.J. from the boy band 3T.
4. Jon Hamm
The Mad Men actor pulled off suits long before his days as Don Draper. He told Jimmy Kimmel that his hair at the John Burroughs School prom was “the beginnings of a mullet”.
5. Ashton Kutcher
The star of Two and a Half Men apparently was the life of the party at his 1996 senior prom at Clear Creek Amana High School in Iowa. Roughly at the same time, his future ex-wife was appearing alongside Burt Reynolds in Striptease.
6. Nicole ‘Snooki’ Polizzi
Long before she became a star of the Jersey Shore boardwalk, Snooki was letting loose at the Marlboro High School prom in 2006.
7. George Clooney
The 1978 graduate of Augusta High School in Kentucky was already bristling with charm at the time, but it took another couple of decades for the world to find out.
Even out of his world-famous drag, RuPaul still managed to stand out at his 1983 prom at Northside High in Atlanta, Georgia.
9. Julia Roberts
America’s Sweetheart was always a pretty woman, as seen in the prom picture she shared on Jimmy Kimmel Live. “There’s a hair shadow that’s making my hair appear much larger than it actually was!”, she said during the show.
10. Taylor Lautner
The Valencia, California cutie left school after his 2008 sophomore year, but returned for the prom. “It was really a lot of fun,” he said.
11. Elizabeth Banks
The star of Pitch Perfect and director of its sequel was voted the prom queen of her Pittsfield, Massachusetts school in 1992.
12. Michelle Obama
The former First Lady looks classy in this prom portrait with her first boyfriend David Upchurch at Chicago’s Whitney M. Young High School in 1981. “That split was a little high. I don’t know if I’d let my kids go out like that,” she admitted on the Ellen DeGeneres Show once.
13. Carrie Underwood
The country music superstar was still an All-American Girl in 2001 at the Checotah High School prom in Oklahoma.
14. Amy Poehler
Widely-known for her sense of humor, Amy Poehler appears indifferent in this photo snapped when she was pulling up to the 1989 Burlington High School prom in Massachussets.
15. Jimmy Fallon
The host of The Tonight Show found time to attend Saugerties High School’s prom in 1992 in New York between airings of his favorite program, Saturday Night Live.
16. Farrah Abraham
The former Teen Mom star confessed that she lost her virginity on prom night with her date Derek Underwood, which led to the birth of her daughter Sophia in February 2009. Tragedy struck shortly afterward when Underwood died in a car accident before the child was born.
17. Halle Berry
Halle Berry was voted cheer captain and prom queen in her senior year of high school in 1984, but her triumph was marred with controversy when she was accused of cheating to win the prom queen title.
18. Lauren Conrad
In 2003, Conrad, then still known as “LC”, made the Laguna High homecoming court while MTV chronicled her senior year on Laguna Beach. Coincidence?
Stacy Ann Furguson lived the glamorous life even before she became Fergie. In 1993, the singer was voted junior princess at the senior prom in Hacienda Heights, California.