How Red Lipstick Changed Lost Girls Into Leading Ladies

The first woman who ever wore red lipstick on-screen was actually a cartoon: Betty Boop, in 1930’s Dizzy Dishes. She had no real dialogue and merely sang a song in her now-iconic shrill pitch. But people don’t really remember specifics of that role. What they do remember is that she wore red lipstick, an indelible image that transcended the fact that she was originally drawn in black and white.

The character was initially illustrated in the likeness of a dog, with floppy ears and a black button nose; only later did Boop get a human upgrade that made her into a bonafide sex symbol. Four years after her debut, she was reintroduced to the world in Technicolor, thereby showing her seemingly black lipstick for what it actually was: bright red.

For centuries, red lipstick has been both a tool for creative expression as well as a weapon of feminine power. In Ancient Greece, it was illegal to wear red lipstick in public unless you were a sex worker. Sex workers made it their signature throughout history, but so did female conquerors and monarchs, like Cleopatra and Queen Elizabeth I. At one point it was outlawed altogether, believed to be the devil’s work and a sign of witchcraft. Still, red lipstick became a commodity, eventually moving from crushed toxic and sometimes lethal ingredients (think sheep sweat and lead) to regulated mass production at the turn of the 20th century. It became something women wanted to accessorize with, in spite of its contentious history.

The color still carries its own set of connotations, even in 2019. The trajectory of its popular perception can be found in Hollywood, on the lips of iconic characters who have graced big and small screens for nearly a hundred years. Boop was presented as a ditzy flapper, but underneath the two-dimensional cartoon lay something deeper. She had something most living, breathing Depression-era women couldn’t access: sexual freedom, or at least the space to flaunt it. She may have had one of the most ridiculous catchphrases (“boop-oop-a-doop”) in Hollywood history, and she spent most of her on-screen time being ogled by men, but her agency was unprecedented for a female character who wasn’t written into the script as a sex worker.

Despite the growing popularity of red lipstick during the 1920s, gaps in technology meant that it couldn’t quite pop on-screen. As with early Boop cartoons, audiences had to use their imagination to see Myrna Loy, Mary Pickford, or Louise Brooks’ black-tinted lips as red. That changed in 1939, with the release of Gone with the Wind. As one of the first movies ever filmed in Technicolor, the color palette of the film was almost as famous as the story itself. Scarlett O’Hara’s glossy red pout, accessorized with actress Vivien Leigh’s trademark scowl and a shockingly low-cut crimson velvet dress, makes its memorable appearance toward the end of the movie, signifying her total disregard for the conventions of Southern propriety that ruled her childhood. 

Women weren’t wearing red lipstick during the Civil War, but they were when Gone with the Wind premiered in 1939, just as the United States economy’s downward spiral was about to look up. Even during the Depression, when industrial production halved, cosmetics sales continued to rise. The goal may have been to stabilize the economy in a time of financial hardship and an impending war, but that didn’t stop women from buying makeup even beyond what their family bank accounts could allow. In 1933, Vogue declared lipstick “the most important cosmetic for women.” Economists eventually dubbed this the “lipstick effect,” noting that something as frivolous as paint for your lips could be both a luxury and necessity to boost spirits when times were tough.

It’s also no coincidence that women’s increased interest in makeup sprouted during the Golden Age of Hollywood, when makeup brands and professional artist unions were birthed behind the scenes. People like Max Factor and George Westmore were monopolizing the film industry (Westmore established the first film makeup department, while Factor’s formulas revolutionized how makeup was made), steering the general public’s interest directly to the beauty counter, where female founders like Elizabeth Arden and Helena Rubinstein were already household names.

A decade after Gone with the Wind, a woman named Norma Jeane Mortenson became Marilyn Monroe, a bombshell with excellent comedic timing — like Betty Boop made flesh. Monroe’s sex-symbol status didn’t come until she underwent a major physical overhaul and was cast in roles meant to weaponize her new look. One bleach job, a seemingly ever-present wash of glossy red lipstick, and a few surgical tweaks later, Monroe emerged fully formed as the biggest movie star of the 20th century.

Monroe’s story is a complicated one, but her on-screen presence often served one simple purpose: To entertain audiences while being the most beautiful thing to look at. As Lorelei Lee in the 1953 film Gentlemen Prefer Blondes, there was nothing she loved more than diamonds and luring rich husbands to buy them for her. Lee looked like a vapid gold digger, but men were only a means to an end for her: Underneath the very surface of the script lived a survivalist, a fact conveyed in the song “Diamonds Are A Girl’s Best Friend.” Her sexual prowess subverted the upper hand of her suitors with one breathy coo through red-painted lips. 

Monroe leaned into her persona as red-lipped seductress off-screen, attracting moneyed men in real life just as she did in her roles as a bombshell. Monroe’s life ended early and tragically, in a death that to this day is shrouded in conspiracy theories, some of which explicitly suggest the actress was murdered as a result of the classified information she kept buried in her affairs. A beautiful woman killed for her secrets? It’s a common trope now, but Monroe may have been its biggest inspiration. She certainly inspired Michelle Pfeiffer’s Batman Returns character, Selina Kyle — better known as Catwoman.

Kyle’s strength is born of trauma: After a violent “death,” she returns as the fierce, latex-wearing, eternally red-lipped anti-hero with a thirst for revenge. Ronnie Specter, personal makeup artist to Pfeiffer for the film, tells Refinery29 that the red lips were meant to look like blood, highlighting the antagonist’s defiance. She was enticing and threatening all at the same time — characteristics she couldn’t possibly evoke with a nude lipstick. Neuropsychologist Sanam Hafeez, MD, echoes what Specter states: If you want attention, you wear red lipstick. Anne Hathaway and Halle Berry also had striking red lips when they took up Catwoman’s mantle.

No iconic character proves that theory better than Jessica Rabbit in Who Framed Roger Rabbit. Rabbit was only a supporting character in the 1988 film, but her seductive performance stole the show — even if she was animated. Like Boop, Rabbit became an instant two-dimensional sex symbol. She was the ultimate fantasy, a mash-up of physical attributes only a male illustrator might conjure: bulging cleavage, cinched waistline, and satin red lips to match her fiery red hair. But like Rabbit says in the movie, she wasn’t bad — she was just drawn that way.

The same can’t be said for Angelina Jolie as Maleficent in the 2014 film of the same name. Jolie’s interpretation of Sleeping Beauty’s tormentor is a villain driven by a complicated and traumatic backstory of betrayal and violence. The film wasn’t exactly a critical darling, but the star’s performance and startling features drew a compelling picture nonetheless. In a 2014 review on Roger Ebert’s site, critic Matt Zoller Seitz called Jolie’s prosthetic-enhanced cheekbones lethal weapons. When combined with her piercing green eyes, wings, horns, talon-like nails, and ruby lips, Maleficent is a stark image of “female otherness,” Zoller Seitz wrote. Maleficent is a fictional creature, but her human experience becomes the beating heart of the film. Underneath the sharp exterior is a woman to be both feared and adored, worshipped and avoided. Other Disney villains who’ve donned red lipstick to let viewers know just how badddd they are include Ursula from The Little Mermaid, Cruella de Vil in 101 Dalmatians, and the Queen of Hearts from Alice’s Adventures in Wonderland.

Despite how attractive a glossy nude lipstick might look on the red carpet, it’s these red-lipped heroines that seem to offer something different, more vibrant, more alive, more daring. These days, the women in red are forces to be reckoned with. Fleabag’s Phoebe Waller-Bridge makes grimacing at the camera even cooler when her lips are painted in a matte shade of red. Likewise, Midge Maisel’s red lipstick serves as a loud, look-at-me contrast to her housewife hairdo on The Marvelous Ms. Maisel. And red lipstick is a powerful signal off-screen, too — even U.S. Representative Alexandria Ocasio-Cortez opts for a polished crimson cream when she needs an extra layer of armor at a congressional hearing. Maybe Monroe was wrong, and diamonds aren’t a girl’s best friend. A bullet of red lipstick is.

—In Partnership with Amazon Prime—