One of the world’s most popular cosmetics, lipstick has historically been not only a tool for enhancing beauty, but also an inspiration for art and architecture, a point of political contention, a clue to crime, and an economic measuring stick. It has signified sexiness and sophistication, countercultural whimsy, female power, male power, safety and danger.

1. LIPSTICK HAD A LONG AND WINDING HISTORY BEFORE THE TUBE

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Before lipstick existed in the way we know it, the Mesopotamians applied colorful jewels to their lips. The ancient Egyptians were also in on the lip-adornment craze, applying a potted dye to their pouts that was comprised of iodine, fucus-algin, and bromine, a combination that was later discovered to be toxic. Cleopatra fortuitously avoided the deadly concoction by using crushed carmine beetles to stain her lips red. Scarlet was still the fashionable color in the 1600s when Queen Elizabeth I (above) offset her powdered face with a red shade made from beeswax, though only a couple centuries later, Queen Victoria would declare makeup to be “impolite.”

2. THE MODERN SWIVEL LIPSTICK BEGAN WITH THE TURN OF A SCREW

In 1923, James Bruce Mason, Jr., of Nashville, Tennessee, patented the first swivel lipstick (he called it a "toilet article," and wrote that it related to "devices for holding articles such as lip sticks which are worn away during the use thereof"). As the lipstick depleted, the user turned a decorative screw head at the base of the tube. Later in the decade, the original “It girl” Clara Bow would make the “Cupid’s bow” style of lipstick application a hit.

3. A KISSING MACHINE WAS INVENTED IN THE QUEST FOR INDELIBILITY

Photo courtesy of The Hollywood Museum

As lipstick became more and more of a commercial success, the mission to make it “kiss-proof” got serious. In 1939, Max Factor, Jr., invented a “kissing machine” comprised of rubber lip molds affixed to a pressure gauge. The machine was designed to give workers on the Max Factor assembly line, who had long tired of kissing tissues, a much-deserved break. The eerie-looking machine would later appear on the cover of the Red Hot Chili Peppers’ 2003 Greatest Hits album.

Despite Max Factor’s best efforts, however, chemist Hazel Bishop became best known for perfecting no-smear lipstick in 1949.

4. LIPSTICK WAS THE CALLING CARD OF A VERY FAMOUS MURDERER

Though lipstick became a way of brightening lips and possibly lives in the ‘40s, it also had a dark side. One of Chicago’s grisliest serial killers took his moniker from the cosmetic. After killing Frances Brown in 1945, someone scrawled in lipstick on her wall, “For heaven’s sake, catch me before I kill more. I cannot control myself.” William Heirens became known as the notorious “Lipstick Killer.” He died at 83 in prison last year.

5. IT WAS ALSO A CLUE TO A NO-GOOD, CHEATIN’ HEART

Rather unfortunately for philanderers, lipstick never truly became completely kiss-proof, as evidenced by Connie Francis’s 1959 chart-topper “Lipstick on Your Collar,” above. “You said it belonged to me, made me stop and think/ Then I noticed yours was red, mine was baby pink,” Francis sang with sorrow. “Who walked in but Mary Jane, lipstick all a mess/ Were you smoochin’ my best friend? ‘Yes,’ he answered, ‘yes.’”

6. LIPSTICK WAS A DEADLY WEAPON DURING THE COLD WAR

Photo courtesy of the International Spy Museum

Luckily for cads like Connie Francis’s man, the KGB never mass-marketed its single-shot pistol called “The Kiss of Death,” designed to look like a tube of lipstick; there would be no crimes of American passion by smoking lipstick gun. But during the Cold War, stealthy female KGB operatives could easily conceal the 4.5 mm weapon and use it to fire at a close, unsuspecting range, according to the International Spy Musuem in Washington D.C. The Kiss of Death pictured above is circa 1965 and is part of the museum’s permanent collection. Though the lipstick pistol is in a classic shade of red, ‘60s Mods were beginning to popularize unconventional lip colors like tangerine, pale pink, silver and even blinding white.

7. AND A TOOL OF PEACEFUL PROTEST DURING VIETNAM

Photo courtesy of Michael Marsland/Yale

In 1969, students at Yale asked Swedish-born conceptual artist and Yale alum Claes Oldenburg to create a sculpture with a revolutionary aesthetic that could also serve as a platform for public speakers during political rallies. The result was an enormous “lipstick” fashioned from red vinyl atop a “war tank” made of plywood, and it commanded a bold and looming presence in the university’s Beinecke Plaza. Oldenburg named the sculpture Lipstick (Ascending) on Caterpillar Tracks (above), and eventually the original materials were replaced with weatherproof steel, aluminum and fiberglass. Oldenburg’s work has been shown at the Guggenheim Museum, the Museum of Modern Art, the National Gallery of Art, and the Whitney Museum of American Art, among others.

Though heavy makeup had been popular during much of the 1960s, hippies had begun to reject makeup entirely in favor of a bare-faced, all-natural aesthetic.

8. SKYSCRAPERS HAVE BEEN BUILT IN THE NAME OF LIPSTICK

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In 1986, another massive “lipstick” was erected, this time between 53rd and 54th Streets at Third Avenue in New York City. Dubbed “The Lipstick Building,” the red granite-and-steel skyscraper was sleek, triple-tiered and tubular, just like a swivel lipstick. Ponzi schemer Bernie Madoff would do much of his scamming on the building’s 17th floor, which became the focus of a New York Times article titled “The 17th Floor, Where Wealth Went to Vanish.”

9. ECONOMISTS USE IT TO NAME “EFFECTS”

Economists use the term “The Lipstick Effect” to explain how, during times of financial hardship, consumers often refrain from buying large-ticket items and instead purchase small goods like lipstick to lift their spirits. (Still, lipstick is one of the most commonly shoplifted products in America, possibly because it can easily fit into a pocket.) But the Lipstick Effect didn’t exactly work to French cosmetics house Guerlain’s advantage in 2007, right before the Great Recession.

In November of that year, Guerlain rolled out a $62,000 lipstick called “Kiss Kiss Gold and Diamonds” that featured an 18-karat gold tube embellished with 199 diamonds. To even think about purchasing Kiss Kiss, one had to make an appointment for a consultation at the upscale Bergdorf Goodman department store in New York City. Reporting on the outrageousness of it all, The New York Post served up its usual headline snark: “Kiss $62K Goodbye."

10. LIPSTICK HAS INCITED POLITICAL MUDSLINGING

Much like “lipstick on your collar” has come to mean “you’ve been runnin’ around on your woman,” the expression “putting lipstick on a pig” has also become part of the popular lexicon. But it wasn’t until the 2008 presidential campaign that we all collectively realized that no one really knows what it means. Serious publications like Slate and TIME devoted articles to tracing the expression’s origins and meaning. Why all the hullabaloo over a silly-sounding expression?

It all started when Obama criticized John McCain and Sarah Palin’s repeated promise of change. “You can put lipstick on a pig, but it’s still a pig,” Obama said. The comment would probably have passed unnoticed had Palin not made a lipstick reference herself the week prior. “You know the difference between a hockey mom and a pitbull? Lipstick,” the proud hockey mom said. The McCain-Palin camp accused Obama of making a not-so-subtle jab at Palin and demanded an apology.

Obama dismissed the accusations, and told David Letterman that the lipstick-pig expression is a common one in Illinois. “Had I meant it that way [as an insult], she would be the lipstick,” Obama said.

11. AND KEPT THE PEACE AT HOME

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Just when it was beginning to seem like Obama had finally lived down that last lipstick-related rigmarole, the president appeared just this last May at a White House-hosted event for Asian American and Pacific Island Heritage Month with … lipstick on his collar.

“A sign of the warmth here is the lipstick on my collar,” he said, pointing to the bright pink stain on his white shirt. “I think I know the culprit. Where is Jessica Sanchez? It wasn’t Jessica, it was her aunt—where is she?” The crowd laughed. “I just want everybody to witness. I do not want to be in trouble with Michelle.”