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25 Totally Awesome & Awkward Yearbook Photos of the Rich & Famous

Yearbook Flashback Old yearbook photos are always entertaining, be it your own, your friend’s or your families. But the ones that really are fun to look at? The yearbook photos of the the rich & famous, the celebrities we know and sometimes love.

From the big hair to the awkward stares to the big glasses,  these 25 photos of celebrity parents can not hide from their past. In some of the photos you can see a hint of the star power they possess but others? They are almost unrecognizable.

Check them out here…which one do you think is the most awkward or the most awesome?


  • Kid Rock 1 of 25
    Kid Rock
    In high school Kid Rock — then known as Robert James "Bob" Ritchie — began his music career, he would DJ at parties for beer.
    Source: Unreality
  • Victoria Beckham 2 of 25
    Victoria Beckham
    Wow, VIctoria Beckham looks so incredibly different in this high school photo, that is not the Posh Spice we know today.
    Source: Ahlan Live
  • Sean Penn 3 of 25
    Sean Penn
    This is such a Spicoli shot, Sean Penn grew up in Santa Monica and looked every part the surfer dude, which helped his career, especially in his iconic role in Fast Times at Ridgemont High .
    Source: Izismile M
  • Mariah Carey 4 of 25
    Mariah Carey
    Mariah started her love of music early on and started taking the prospect of being a singer seriously while she was at Harborfields High School in Greenlawn, New York.
    Source: Amy Grindhouse
  • Gwen Stefani 5 of 25
    Gwen Stefani
    Gwen Stefani made her performing debut at Loara High School in Anaheim, California when she performed, "I Have Confidence", from The Sound of Music
    Source: Amy Grindhouse
  • Amy Adams 6 of 25
    Amy Adams
    Amy Adams looked very much fresh faced and sweet in her photo from her senior year, Douglas County High School, Castle Rock, CO.
    Source: Celebrity Year Book
  • Matt Damon 7 of 25
    Matt Damon
    Matt Damon began acting in high school, starring in several school production before graduating and going to Harvard.
    Source: Amy Grindhouse
  • Angelina Jolie 8 of 25
    Angelina Jolie
    Angelina Jolie went to the famous Beverly Hills High School (of 90210 fame) but felt like an outcast at the school.
    My 10 Online
    Read more about Angelina's high school years here.
  • Brad Pitt 9 of 25
    Brad Pitt
    Brad Pitt was very busy at Kickapoo High School in Springfield, Missouri partaking in basketball, golf, tennis, wrestling and swimming teams. As well as performing in school musicals.
    Source: Allie Is Wired
  • Tom Cruise 10 of 25
    Tom Cruise
    After graduating from Glen Ridge High School in New Jersey Tom Cruise moved to New York City to take on the acting world...and his plan worked!
    Read more about Tom Cruise's youth right here.
    Source: Unreality
  • Madonna 11 of 25
    Madonna
    Such a young image of the Material Girl, Madonna went to Rochester Adams High School in Michigan and was quite the student where she was a straight-A student and also a member of the cheerleading squad.
    Source: Izismile M
  • Katie Holmes 12 of 25
    Katie Holmes
    Katie Holmes went to the all-female Notre Dame Academy and would participate in school plays at the all-male school nearby.
    Source: Allie Is Wired
  • Jessica Simpson 13 of 25
    Jessica Simpson
    Jessica went to J. J. Pearce High School but dropped out to focus on her career, she later earned her GED.
    Source: Amy Grindhouse
  • Halle Berry 14 of 25
    Halle Berry
    Halle Berry was quite the overachiever at Bedford High School. She was a cheerleader, class president, and their prom queen.
    Oh Verly Critical
  • Milla Jovovich 15 of 25
    Milla Jovovich
    Born in the Ukraine, Milla moved to America when she was five and went to a public high school in Los Angeles.
    Source: Amy Grindhouse
  • Sharon Stone 16 of 25
    Sharon Stone
    Sharon graduated in 1975 from Saegertown High School in Saegertown, Pensylvannia. A classmate of Sharon's said that she was a "exhuberant, active and well-liked girl. She always appeared to me to be in an eternal good mood. She smiled all of the time I was around her. "
    Source: Sharon Stone.net

    Source: Amy Grindhouse
  • Jennifer Hudson 17 of 25
    Jennifer Hudson
    Jennifer Hudson grew up in Chicago and reportedly told her music teachers that she would famous some day.
    Source: JenniferHudson.Com
  • Demi Moore 18 of 25
    Demi Moore
    Demi Moore quit high school at the age of 16 to move to Europe to do modeling.
    Source: Amy Grindhouse
  • Beyonce 19 of 25
    Beyonce
    Beyonce honed her skills at the High School for the Performing and Visual Arts in Houston and then later went to Alief Elsik High School in the suburbs. She looks so young is this photo!
    Source: Celebrity Year Book
  • Paul Rudd 20 of 25
    Paul Rudd
    Paul went to Shawnee Mission West High School in Kansas, and looking at this photo, you'd never know he'd grow up to be a movie star.
    Source: My 10 Online
  • Uma Thurman 21 of 25
    Uma Thurman
    Uma started working as a model at the young age of 15, so she was a working high schooler.
    Source: Allie Is Wired
  • Julia Roberts 22 of 25
    Julia Roberts
    Julia went to Campbell High School in Georgia. And that smile is just so Julia!
    Source: My 10 Online
  • Eminem 23 of 25
    Eminem
    Eminem actually quit high school in 9th grade so this is his only high school photo!
    Source: Amy Grindhouse
  • Charlize Theron 24 of 25
    Charlize Theron
    Charlize once talked to People Magazine about how she didn't fit in in High School saying, "I wore really nerdy glasses because I was blind as could be and the boys didn't like [me]," the actress said. "I didn't have any boyfriends, but lots of crushes."
    Source: People
    Source: Blame it on the voices.com
  • Harrison Ford 25 of 25
    Harrison Ford
    Before he was Hans Solo and before he was Indiana Jones, he was just a boy in high school! He went to Maine East High School in Park Ridge, Illinois and was the school sportscaster in his senior year.
    Source: My 10 Online
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