Oscars Makeup Artist Picks His Top 10 Oscars Beauty Looks of the Decade

11:49 AM 2/6/2020

by Ingrid Schmidt

"I feel like I’m the Boy Scout of makeup artists," says Bruce Grayson, Oscars head of makeup, who reveals what's in his beauty kit and his favorite red carpet looks since 2010. "I always come prepared!"

From left: Jennifer Lawrence in 2011, Emma Stone in 2015, Zendaya in 2018
From left: Jennifer Lawrence in 2011, Emma Stone in 2015, Zendaya in 2018
Jeff Vespa/WireImage; Steve Granitz/WireImage; Frazer Harrison/Getty Images

Having served as the head of makeup of the Oscars telecast for 19 years, Emmy-nominated makeup artist Bruce Grayson has seen his share of cosmetic meltdowns on Hollywood’s biggest night.

For the 92nd Academy Awards on Sunday, Grayson will oversee a team of 20 makeup artists, whose main mission is to touch up the presenters before they appear onstage, as well as the winners that need a fast fix before heading to the press room.

“It’s the Super Bowl of awards shows,” Grayson tells The Hollywood Reporter. “I feel like I’m the Boy Scout of makeup artists; I always come prepared! We deal with a lot of tears. There are tears of joy and tears of sadness. The repairing of eye makeup is what we do the most of."

On show night, he “can’t live without” blotting papers, a Beautyblender makeup sponge, top-notch translucent powder by Chanel or Giorgio Armani, Laura Mercier Secret Camouflage concealer, Giorgio Armani Luminous Silk Foundation and four eyeliner pens by MAC, Stila and Armani.

More unexpected items in his kit include styptic powder and liquid bandages to treat shaving nicks and cuts; at least six types of eyedrops to lubricate, treat redness and accommodate various contact lenses; and a vast collection of breath mints, sprays and strips.

A memorable moment last year occurred when Grayson lost a bet with 2018 Oscar-winning director Guillermo del Toro over who would take home the best director prize in 2019, and del Toro (who accurately predicted Alfonso Cuarón) came back to collect his $5. “And there have been many years when Meryl Streep came in to watch the whole show in the privacy of our little makeup room with us, rather than with everybody in the green room, because it can get so noisy in there,” he says.

As for trends to expect at the 2020 Oscars, Grayson says, “It wouldn’t be the Oscars unless we saw a red lip. Right now, matte lipstick is very popular on the carpet, so I’m curious to see who wears a great matte reddish-brown lipstick to contrast with a gown. That’s a look I love.”

Here are Grayson’s favorite beauty looks at the Oscars during the past decade.

  • Jennifer Lopez in 2010

    "Jennifer Lopez wearing the Giorgio Armani Prive Gown, smoky eyes with a pale pink lip, and loosely pulled back hair. It’s the perfect balance of glamour."

  • Jennifer Lawrence in 2011

    "Jennifer Lawrence wearing the scarlet Calvin Klein Collection dress, casual loosely waved hair, dark smoked eyes and nude lip — a winning red carpet moment."

  • Rooney Mara in 2012

    "Rooney Mara in a white plunging Givenchy Couture dress paired with the strong bang, glossy chignon hair, and strong eyebrow and red lip. It’s a strong and beautiful look."

  • Jessica Chastain in 2013

    "Jessica Chastain in the nude Armani Prive gown, soft waved hair, simple black eyeliner, and a classic red lip screams ‘movie star.'"

  • Lupita Nyong’o in 2014

    "Lupita Nyong’o wearing the sky blue V-neck Prada gown. I love the orange lipstick [and] strong eyebrow: a stunning combination."

  • Emma Stone in 2015

    "Emma Stone in the green beaded Elle Saab gown. [It’s about] contrast: Her beautiful red hair, part-up-part-down, the perfect eyebrow and that strong orange red lip is an overall slam-dunk beauty moment."

  • Olivia Wilde in 2016

    "Olivia Wilde in the Valentino haute couture dress with the braided up 'do, strong eyeliner and soft lip is an ultra elegant Oscar look."

  • Olivia Culpo in 2017

    "Olivia Culpo dressed in a Marchesa detailed gown, sleek ponytail with bangs, stunning lavender eyeshadow and pale lip. I love everything about this look."

  • Zendaya in 2018

    "Zendaya wears a brown one-shouldered Giambattista Valli gown with sleek top bun hairstyle, bronzed face, dark sweeping eyes and soft nude lip. The look screams Grecian goddess."

  • Kacey Musgraves in 2019

    "Kacey Musgraves in the pale pink tulle Giambattista Valli couture gown, hair parted in the middle and pulled back, and gorgeously executed makeup with strong brows and pale lip. It’s a fairy tale beauty moment."