1 / 12

Bando Tamasaburo V, 1996

These 12 Men Made Makeup Look Good

Vogue

By Mackenzie Wagoner. Photos: Getty; Everette.

Yesterday, after 58 years in the business, CoverGirl introduced its first CoverBoy, James Charles, a 17-year-old makeup artist from New York. The social media sensation has accrued over half a million Instagram followers with his dramatic how-to transformations and lawless approach to makeup. For Charles, no color is off limits, no highlight too daring. And while he may be the first man to earn a starring spot in a CoverGirl commercial, he joins an impressive history of men who have dipped into makeup bags with abandon, to great success.

After all, it was the moment David Bowie ditched his image as just another long-haired crooner from Brixton for the otherworldly and heavily made-up Ziggy Stardust that he experienced a meteoric rise to fame.While some critics found Bowie’s chromatic, gender-bending looks a distracting display of smoke and mirrors, the Pierre La Roche–designed celestial makeup had a resounding influence. Contemporaries and collaborators Mick Jagger and Marc Bolan also exhibited a flair for cosmetics, using daubed-on eyeliner and splashes of glitter to set themselves apart from the average frontman, finding that femming up their looks only heightened their masculine edge onstage.

Not long after the glam rock ’70s came the culture club ’80s, where the likes of Leigh Bowery and Boy George made a habit of dressing as though their lives depended on it, down to the angular flush of their cheeks. Across town, while Bryan Ferry waxed poetic on redecorating Roxy Music’s hotel rooms, bandmate Brian Eno could be found in front of their best-lit mirrors, strategizing oblique slashes of blue eyeshadow and multi-tonal hair chalk. Robert Smith and, later, Marilyn Manson enjoyed the unease their powdered porcelain skin, dark black eyeshadow, and blood-stained lips caused on the streets. It’s an effect Manson enhanced with a milky white eye contact—perhaps a wink at Bowie’s arresting, permanently dilated pupil?

Of course, glam rock was not the first case of men wearing makeup, either. Before Bowie sang “I’m an alligator,” he learned the art of kabuki makeup from Japan’s most famous onnagata, Band? Tamasabur? V, and he also spent considerable time among mimes, training with Lindsay Kemp in the 1960s. And where would dancer Vaslav Nijinsky or actor Rudolph Valentino have been without the transformative power of makeup? In honor of James Charles’s groundbreaking new role, a look back at 17 men who made wearing makeup look like the most masculine thing a person could do.

This story originally appeared on Vogue.

More from Vogue:

The Best Celebrity Engagement Rings

The Best Hourglass Bodies of All Time: From Raquel Welch to Beyoncé

22 Secret Celebrity Weddings We Still Know Little About

See All The Stunning Looks From The 2016 Emmy Awards

The 27 Best Celebrity Beach Bodies of All Time

Check Out The Best Dressed Celebrities From The 2016 MTV VMAs