Hot Gallery: From Ingénue to Centerfold, Snakkle Looks Back at Playboy Cover Girls Before They Were Famous

jaime pressly yearbook high school 1993 photo

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Jaime Pressly, High School Yearbook, 1993

This Costa Mesa High School sophomore turned model turned actress might tell you her name isn’t Earl (or Joy, for that matter), it’s Jaime. If you have trouble remembering now, we bet you won’t once you see her Playboy cover.

jaime pressly yearbook high school 1993 photo playboy cover 2004

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Jaime Pressly, Playboy Cover, 2004

She might not have been the star of the film I Love You, Man, but we’re guessing even Hef thought that when he saw this picture of Jaime.

lindsay lohan young red carpet 2002 photo

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Lindsay Lohan, Treasure Planet Premiere, 2002

Before Lindsay was a mean girl or had freaky Fridays (or, let’s face it, legal problems), this freckle-faced starlet might have told herself to beware of the real-life parent trap ahead.

lindsay lohan young red carpet 2002 photo playboy cover 2012

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Lindsay Lohan, Playboy Cover, 2012

Happy holidays to Lilo, indeed, and the reported million dollars she received for this spread. Hopefully that covered her legal fees for the month.

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Charlize Theron, 1992

This South African dancer turned model might tell herself she is wise to remain natural and hang on to these girl-next-door days.

charlize theron young 1992 photo playboy cover 1999

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Charlize Theron, Playboy Cover, 1999

Hard to believe this hands-on beauty would one day grow up to play a Monster so convincingly that she would win the Oscar for Best Actress in 2004.

marilyn monroe yearbook high school 1953 photo

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Marilyn Monroe, High School Yearbook, 1942

Still Norma Jeane Baker, this 10th grader at SoCal’s own University High might have told herself blondes have more fun!

marilyn monroe yearbook high school 1953 photo playboy cover first issue 1953

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Marilyn Monroe, First Issue Playboy Cover, 1953

Marilyn has something to celebrate, all right: She graced the cover of the very first issue of Playboy!

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Madonna, 1979

When this material girl was just learning how to give good face, she might have told herself last names are overrated. That, and rosary beads are the new black.

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Madonna, Playboy Cover, 1985

Jim might have been desperately seeking Susan, but Hef was definitely seeking Madge. Like a virgin, posing for Hugh for the very first time…like a viiiir-gin… (C’mon, sing it with me!)

drew barrymore young red carpet 1991 photo

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Drew Barrymore on the Red Carpet, 1991

Drew and her Calvins must have told herself that she could be like Marky Mark and bare some skin. It seems not everyone needs a funky bunch to give good vibrations.

drew barrymore young red carpet 1991 photo playboy cover 1995

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Drew Barrymore, Playboy Cover, 1995

With a butterfly on her belly, sin in her eye, and a then recent string of titles under her belt like Bad Girls, Boys on the Side, and Mad Love, Drew had her coming-out party Barrymore style, flaunting it all in this pictorial.

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Sharon Stone, High School Yearbook, 1970

When this Saegertown, Pennsylvania, seventh grader debated growing out her bangs, she might have told herself to go with her basic instinct.

sharon stone yearbook young 1970 photo playboy cover 1990

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Sharon Stone, Playboy Cover, 1990

Sharon proves that 32 is not too old to bare it all. But then, we can’t all look like Sharon Stone at 32.

brooke burke yearbook high school young 1986 photo

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Brooke Burke, Yearbook Photo, 1986

This freshman at Sahuara High School in Tucson, Arizona, might go back and tell herself to trade her curling iron for a pair of Skechers. Normally Brooke Burke’s toned bod is what catches your eye, but we can’t keep our eyes off that hair. Glad you figured it out and shaped up, Brooke!

brooke burke yearbook high school young 1986 photo playboy cover 2004

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Brooke Burke, Playboy Cover, 2004

She may have been a Valerie Bertinelli look-alike back in the day, but this Dancing with the Stars alum and cohost is proof that you can still be a mom and be sexy even without Jenny Craig. Va-va-voom, Brooke!

carmen electra yearbook young 1985 photo

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Carmen Electra, Yearbook Photo, 1985

Though only in seventh grade, Carmen was already showing the confidence of a performer back at Cincinnati's School for Creative and Performing Arts. Maybe she told herself, “Don’t worry about the snaggle tooth, girl. When you grow up, you are going to be on magazine covers and marry rock stars and NBA players.”