Hot Mama… Alyssa Milano: From Tomboy Child Star to Maxim Cover Girl!

Alyssa Milano

Shining an adorable smile in a Peter Pan-collared dress (and check out that epic Sears portrait backdrop), Milano had star power even as a young girl.

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Alyssa Milano as Samantha Micelli on Who's the Boss?

In 1984, Milano started out playing the tough tomboy Sam, who always ran home with a scraped knee or black eye. As Sam grew, she tossed out the baseball caps and pigtails for scrunchies and leggings. Next stop, teen idol.

Alyssa Milano Junior Year, Buckley School, Sherman Oaks, CA, 1990

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Alyssa Milano at Buckley School (1990)

Alyssa Milano looks like she's either very studious or trying to blow up her computer telekinetically during her junior year at Buckley School in Sherman Oaks, CA. We'll let you be the judge.

Alyssa Milano as Jenny Matrix in Commando (1985)

Alyssa Milano as Jenny Matrix in Commando (1985)

Check out the awesome '80s hair and duds Milano sported in the Arnold Schwarzenegger action vehicle Commando. Milano (natch) played Arnold's kidnapped daughter Jenny.

Alyssa Milano as Teen Samantha Micelli on Who's the Boss

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Alyssa Milano as Teen Samantha Micelli on Who's the Boss?

As she grew, thousands of teenage boys realized that Milano was drop-dead gorgeous underneath the tomboy clothes and baseball caps. Their parents wondered why they had such a sudden interest in that quirky sitcom about the male housekeeper.

Alyssa Milano as Chelsea in Glory Daze (1995)

The question isn't who stars in this little-known indie movie about friends struggling with graduation from college... the question is who doesn't? Milano appears alongside pre-fame Ben Affleck, Matt Damon, Matthew McConaughey, and Sam Rockwell. We know what's going on your Netflix queue this weekend.

Alyssa Milano in Poison Ivy 2: Lily (1996)

Milano attempted to break out of her wholesome Who's the Boss? image by starring in a sequel to the Drew Barrymore shocker Poison Ivy. Mission accomplished.

Alyssa Milano as Margo Masse in Fear (1996)

Milano, in another grown-up role, starred alongside Reese Witherspoon and Mark Walhberg in the thriller Fear.

Alyssa Milano as Jennifer Mancini on Melrose Place

Alyssa Milano as Jennifer Mancini on Melrose Place

There are bad girls and then there are Melrose Place bad girls. Milano sunk her teeth into playing baddy Jennifer Mancini back in 1997.

Alyssa Milano as Phoebe Halliwell in Charmed

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Alyssa Milano as Phoebe Halliwell in Charmed

WB fans went nuts over a show about sisters Phoebe (Milano), Piper (Holly Marie Combs), Prue (Shannen Doherty), and later Paige (Rose McGowan), who led normal lives until they disocovered they were "good" witches. Charmed was a huge rating hit and continued on The WB from 1998 to 2006.

Alyssa Milano as Billie Cunningham in My Name Is Earl

Alyssa Milano as Billie Cunningham in My Name Is Earl

Milano got to go back to her comedy roots with a short run as Earl's wife in NBC's hit My Name Is Earl.

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Alyssa Milano Becomes a Mom

Milano, now 38, seems happily settled. She married CAA agent David Bugliari in August of 2009 and gave birth to a healthy son, Milo Thomas Bugliari, on August 31.

Alyssa Milano in New Year's Eve (2011)

Milano joined a cast of thousands (OK, it just seemed like thousands) of Hollywood A-Listers in Garry Marshall's holiday vehicle, New Year's Eve. She plays Mindy, a nurse caring for an elderly patient who has nobody to ring in the new year with—we bet she takes pity on the poor fella and gives him a smooch at midnight.

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Alyssa Milano in 2012

Milano shows off her post-baby glow at the premiere of her recent film, New Year's Eve.

Alyssa Milano on the July 2013 Cover of Maxim Magazine

Dang. 40 years old and making it look easy, Milano looks smokin' on the July cover of Maxim magazine. After growing up on TV and in front of our eyes, Milano is now married and the mother of one. She really is the boss!