Madonna's Changing Looks

The Rochester Adams High School cheerleader plucked her brows pencil-thin and played up her eyes with soft liner.

For her acting headshot, the new New Yorker sported wild crimped hair and wispy bangs.

Madonna goes punk: the Manhattan scenester rocked a gelled crop, heavy lipstick and artfully applied shadow.

She released her self-titled debut album and brought downtown N.Y.C. club style to the masses.

Her album Like a Virgin sold millions of copies, but her look was pure D.I.Y.

"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."

"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.

She channeled a geisha for the Cannes Film Festival premiere of Madonna: Truth or Dare.

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.

Madonna went au naturel for an Evita screening with soft wheat-blond curls and understated makeup.

Dark, dramatic red lips and hair for the launch of Ray of Light.

For the launch of Music, Madonna chose candy-colored purple shadow and patent fuchsia lips.

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."

Madonna went disco for Confessions on a Dance Floor with feathered locks and sparkling shadow.

She hit the post-Oscars parties with Marilyn waves and pretty peach lips.

Madonna celebrated a milestone birthday and released her 11th album, Hard Candy. "At 50, she's even more experimental," says Brooke.

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."

Madonna went soft for an N.Y.C. benefit with retro waves, mega lashes and barely-there makeup.

"Madonna wanted easy natural texture hair," Wella Professionals hairstylist Andy LeCompte said of her Globes look.

The icon goes for a faux bob, keeping her signature blonde hairdo.

Madonna opts for a black hat and accompanying grill (not pictured).

At the Grammys, Madonna channeled a matador for her red carpet and on-stage outfits.

At the 2016 Met Gala, the 57-year-old star chose loose waves and a jeweled headpiece to accompany her racy cutout dress.