August 21, 2006 12:00 PM


Charlize Theron, ca.1994

Before she won an Oscar, Theron modeled lingerie and worked the catwalk in Milan.

Tom Cruise, 1984

Right after strutting his stuff in tighty whities in Risky Business, a young Tom Cruise flashed his guns—and an early prototype of his patented grin—for the camera.

Ashton Kutcher, 1995

Demi Moore, 1981

Pulling a Marky Mark in Calvin Klein underwear, he found steady work as a model. A few years earlier, his future wife did what she could with that ’80s curse: the superfluous ruffle.

Keanu Reeves, 1988

Dude, where’s my scrunchy? Once called “a beautiful man in an androgynous way” by a photographer, Reeves hit the big time in 1989’s Bill & Ted’s Excellent Adventure.

Brad Pitt, 1988

Someday, people would actually want to see this man with his shirt off. But doing this hokey-pokey pose was a good gig for struggling model-actor Pitt. Another job? Chauffering a limo for a strip-o-gram service.

Gwyneth Paltrow, 1989

Back when she was just Blythe Danner’s kid, Paltrow appeared in an ad campaign to promote safer sex for high school students.

Before They Were Feuding

Heather Locklear, 1979, vs. Denise Richards, 1989

With nary a rock star in sight, Locklear happily reigned as senior princess at Newbury Park (Calif.) High School, while Richards spent her teen years as a model down the coast in Oceanside.

Nicole Richie vs. Paris Hilton, ca. 1991

Back when life was simple, Hollywood curiosities Hilton and Richie were, in their words, “best pals since we were babies” at the Buckley School in Sherman Oaks. What did the divas-in-training do for fun? Play soccer.

Star Jones, 1995, vs. Barbara Walters, 1967

Once known for battling lawyers, not cohosts, as a full-figured Brooklyn assistant D.A., Jones still regards her former boss, ’60s and ’70s Today show anchor Walters, as “everything I want to be in a broadcaster.”


Nick Lachey 1991

Easing on down the road as the Lion in Cincinnati’s School for Creative and Performing Arts’ production of The Wiz. Other credits? Peter Pan with classmate Carmen Electra.

Matt Damon, 1986

Sure, he has an Oscar, but who could forget Damon’s portrayal of Humpty Dumpty in Bravo Cappuccio! in the New England Drama Festival? Especially after seeing that costume.

Kenny Chesney 1986

Nowadays he’s famous for his 29″ jeans, but for spirit day in high school, Chesney tried a miniskirt on for size (he stuck with hats).

Angelina Jolie 1988

Somewhere, Boy George is missing his hat. But proto-Goth Angelina Jolie would soon grow into her looks and appear in the Rolling Stones video “Anybody Seen My Baby?”


Matthew McConaughey 1988

Hey, anybody know a dork these guys can give a wedgie to? Even when he was back at Longview High in Texas, future Sexiest Man Alive McConaughey was a popular golf and tennis player with no shortage of female admirers. “I’m telling you, those girls liked his butt,” his mom told PEOPLE.

Jessica Simpson, 1995

The future pop queen was so loved at Richardson High in Texas she was named sophomore homecoming princess. Years later she’d replace all those ribbons with killer hair extensions.

Matthew Fox, 1984

Raised on a ranch, he played football at Wyoming’s Wind River High. But he still couldn’t pull off a white tuxedo at his senior prom.

Sean Combs 1987

At Mount St. Michael Academy in the Bronx, Pre-Diddy was already dressed for success.


Katie Couric, 1975

While the Captain & Tenille hit No. 1 with “Love Will Keep Us Together,” this short and sassy cheerleader wowed ’em with no-hands cartwheels at Yorktown High in Arlington, Va.

Sandra Bullock, 1982

Seven years after Couric pepped up Arlington, fellow resident Bullock put junior high geekiness behind her by making the squad at Washington-Lee High. Go, Generals!

Cameron Diaz, 1988

The 5′9″ “Polyette” at Long Beach Polytechnic was only 16 when a modeling scout spotted her on a night out in Hollywood.

Halle Berry 1980

Gimme a V! Berry led the cheers at her junior and senior high schools in Bedford, Ohio, before splitting to pursue a modeling career in Chicago.

Before They Got Dates

George Clooney
A living testament to the power of contact lenses, this goofy guy would later be sexy enough to own his own Italian villa!

Jamie Foxx

Back in 1986, when he was Eric Bishop, Foxx, 38, battled a serious Jheri curl dependency as a trumpet player at Terrell High in Terrell, Texas.

David Spade

Nobody could be looking forward to the class of 1982 reunion more than this man, who grew up to hang with that cute girl from T.J. Hooker.


Britney Spears, 1997, and Kevin Federline, 1988

Post-Mouse Club Britney played basketball for Mississippi’s Park Lane Academy. The future K-Fed had already been voted Most Likely to Be on America’s Most Wanted at Fresno’s Tenaya Middle School.

Nicole Kidman, 1971, and Keith Urban, 1972

Proving that America has no corner on ambitious child performers, these two talented tots came of age in ’70s Australia. By age 4, Kidman had mastered her Serious Actress Look. Meanwhile, little Keith had mastered … the ukulele? Says neighbor Anna Miletic: “He always had a guitar in his hand.”

Vince Vaughn, 1988, and Jennifer Aniston, 1987

As the host of his Lake Forest (Ill.) High School talent show, Vaughn “was hysterical,” says his volleyball coach Chris Eiserman. Aniston, meanwhile, channeled her inner Joan Jett while at New York’s Fiorello H. LaGuardia High School for the performing arts, admitting she “did liquid eyeliner better than anyone in history.”

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