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1975
The Rochester Adams High School cheerleader plucked her brows pencil-thin and played up her eyes with soft liner.
1978
For her acting headshot, the new New Yorker sported wild crimped hair and wispy bangs.
1979
Madonna goes punk: the Manhattan scenester rocked a gelled crop, heavy lipstick and artfully applied shadow.
1983
She released her self-titled debut album and brought downtown N.Y.C. club style to the masses.
1984
Her album Like a Virgin sold millions of copies, but her look was pure D.I.Y.
1985
"This was the Like a Virgin era," makeup artist Gina Brooke has said of Madonna's American Music Awards look. "She laughs about how she did her own makeup."
1987
"The red lips and beauty mark were her signature at the time," Brooke said of Madge's take on Marilyn. Messy platinum waves and unkempt brows completed the Who's That Girl look.
1991
She channeled a geisha for the Cannes Film Festival premiere of Madonna: Truth or Dare.
1995
For the MTV Video Music Awards, the Bedtime Stories singer got inspired by another beauty icon. "This is very Catherine Deneuve in Belle de Jour-big hair with lots of teasing," said hairstylist Garren.
1996
Madonna went au naturel for an Evita screening with soft wheat-blond curls and understated makeup.
1998
Dark, dramatic red lips and hair for the launch of Ray of Light.
2000
For the launch of Music, Madonna chose candy-colored purple shadow and patent fuchsia lips.
2003
She debuted her first children's book and took on a mature new look. "Her eyes are her best feature," says Brooke. "She has fun playing them up with liquid liner."
2005
Madonna went disco for Confessions on a Dance Floor with feathered locks and sparkling shadow.
2007
She hit the post-Oscars parties with Marilyn waves and pretty peach lips.
2008
Madonna celebrated a milestone birthday and released her 11th album, Hard Candy. "At 50, she's even more experimental," says Brooke.
2009
The icon inspired again with the dramatic looks for her "Sticky and Sweet" tour. "She doesn't take on trends, she creates them," says hairstylist Andy LeCompte. "That's why she likes taking risks."
2010
Madonna went soft for an N.Y.C. benefit with retro waves, mega lashes and barely-there makeup.
2012
"Madonna wanted easy natural texture hair," Wella Professionals hairstylist Andy LeCompte said of her Globes look.
2013
The icon goes for a faux bob, keeping her signature blonde hairdo.
2014
Madonna opts for a black hat and accompanying grill (not pictured).
2015
At the Grammys, Madonna channeled a matador for her red carpet and on-stage outfits.
2016
At the 2016 Met Gala, the 57-year-old star chose loose waves and a jeweled headpiece to accompany her racy cutout dress.
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