Say Cheese!

Awkward Celebrity Prom Pics: Michelle Obama, Brad Pitt, More (PHOTOS)

From Michelle Obama showing some skin to Will Ferrell in a bejeweled crown, see stars on their prom night.

Splash News (2); Newscom

Splash News (2); Newscom

Prom season is in full swing, and you know what that means—box tuxedos, up-dos, corsages, and inevitably cringe-inducing prom date photos. From Michelle Obama showing some skin to Brad Pitt’s one-finger grip on his date’s arm, see stars on their prom night.

Splash News

Michelle Obama

Before she became the stylish first lady of the United States, an 18-year-old Michelle Robinson made a bold fashion statement as prom queen in an exotic gold dress with a sexy, skin-revealing slit. And we have to admit, she looks quite regal on her wicker chair.

Seth Poppel / Yearbook Library

Will Ferrell

Apparently, funnyman Will Ferrell was peeved he didn’t get a crown as prom king. Naturally, he stole his date’s bejeweled headpiece for this epic photo.

Splash News

Brad Pitt

Brad Pitt’s date looks pretty elated on her prom night, despite Pitt’s awkward one-finger grip on her arm. At least she was tan for the photo (no, those aren’t straps on her cupcake dress).

Seth Poppel / Yearbook Library

George Clooney

Did George Clooney get into the spiked punch, or were his bedroom eyes just more pronounced when he still had that baby face? Either way, he looks every bit the suave ladies’ man.

Gary Miller / Splash News

Sarah and Todd Palin

Considering this photo of Sarah and Todd Palin was taken in the ’80s, the most awkward thing about it is how they both look pretty normal. Oh, and that demonic-looking chair that’s creeping up behind them.


Natalie Portman

She’s got the shawl, the corsage, the sparkly dress and purse to match, but where’s her date? Natalie Portman looks like she just wants to get out on the dance floor. Good thing she got her chance in Black Swan.

Seth Poppel / Yearbook Library

Courteney Cox

In Birmingham, Ala., in 1980, apparently the farm girl look was in, judging from the apron-style dress Courteney Cox wore to her prom.

Seth Poppel / Yearbook Library

Dick Cheney and Lynne Cheney

It’s not every day you go out with a future U.S. vice president. Let’s hope Lynne Cheney was focused on that and ignored her dream of holding hands with her prom date.

Seth Poppel / Yearbook Library

Mitt Romney

Something funny just happened at Mitt Romney’s table, but it does not appear as if he gets it.

Seth Poppel / Yearbook Library

Meg Ryan

Actress Meg Ryan looks like she was having a great time in her 1979 prom photo. It’s just too bad the same can’t be said of her date.

Courtesy Bedford High School / Zuma Press

Halle Berry

Not surprisingly, Halle Berry was the prom queen at Bedford High School, near Cleveland, in 1983. The race was so close that a coin-toss declared Berry the winner. It’s mostly awkward because it looks like her competition may have been a 5-year-old girl.

Seth Poppel / Yearbook Library

George H. W. Bush

Who’s leading whom? George H.W. Bush looks kind of cute in this dance-floor photo-op at Phillips Academy’s prom in 1942.