Top 10 Moments in Underwear History

by Danny Schmittler

Underwear hasn’t been in the spotlight for as long as, say, Justin Bieber’s haircut, but it sure has earned its place in history. From celebrities showing more than they should to brushes with the law, these moments no doubt changed the trajectory of human life as we know it. Bet you didn’t think of that when you put on your skivvies this morning. We’ve compiled the top 10 underwear moments in history for you to read, remember, and ultimately ask, “Where the heck was I when that happened?” Take a gander at these photos commemorating each moment, and then read about each of the Top 10 moments in underwear history after the jump!

1983: Tom Cruise Takes a Risk

Bob Seger’s “Old Time Rock and Roll” instantly stopped being about rock and roll and quickly became “that song that we listened to when we were looking at Tom Cruise’s junk” after Tom Cruise slid across the floor wearing an open button down shirt and white briefs in the 1983 movie Risky Business. Thank goodness he kept his clothes on when he rocked and rolled on Oprah’s couch over 20 years later.

1985: Joe Boxer Breaks the Law

When Canadian-born necktie designer Nick Graham ran out of fresh undies, he gave up the tie business altogether and started Joe Boxer, an underwear brand featuring fun designs that were meant to be seen. His first style, which was carried by Macy’s, featured a removable raccoon tail. Later that year, the company made headlines when boxers printed with $100 bills were found by the Secret Service to be in violation of federal forgery laws. Oops? Riding the wave of rebellion that defined the 80s, it’s no wonder that 25 years later, Joe Boxer is still around and that the signature yellow smiley face–aptly named Mr. Licky–is still sticking his tongue out at us.

1985: Marty McFly as Calvin Klein

In the first Back to the Future, Marty McFly (played by Michael J. Fox) finds himself  30 years in the past, in 1955, waking up in his mother’s bed. What really confuses him, though, is that everyone keeps calling him “Calvin.” The reason? His purple Calvin Klein Underwear, which hopped to the 50′s with him. After that scene, any teenage boy caught in anything other than Calvins just wasn’t really that cool.

1990: Madonna Gets Over Underwear

The Jean Paul Gaultier-designed wardrobe for Madonna’s “Blond Ambition” World Tour questioned the whole “under” part of underwear when the singer stepped onstage proudly flaunting heavily embellished versions of the undergarments most women strive to keep hidden. The show’s opening costume featured a suit with slits cut into the jacket, allowing the iconic cone bra beneath to poke out and be seen by all. Since then the cone bra has become synonymous with both Madonna and sexually liberated women everywhere.

1992: Marky Mark Drops Trou

During a performance of his dance hit and 90s cheerleading anthem “Good Vibrations,” Rapper Marky Mark (aka Mark Wahlberg) dropped his pants, revealing his Calvin Klein Underwear tighty whities. Many a rapper before and since have worn their pants low, but Marky Mark was the first to go all the way and the only to make pants-dropping his signature, a move that would prove smart as it later earned him the chance to model for the company.

1994: Bill Clinton Debriefs His Underwear Preference

“Cool” President Bill Clinton rewrote protocol when asked the question heard round the world–”Boxers or Briefs?”–by an audience member on MTV’s Enough is Enough and actually answered. Mind you, this was in the second year of Clinton’s presidency, which shows he was making the sexual rifts well ahead of the Monica Lewinsky scandal. In case you were wondering, his answer was “Usually briefs.”

1999: The Naked Cowboy

He may have started out as a small-time street performer, making the corner of 42nd Street and Broadway in Times Square his stage to a daily crowd of tourists, but on November 13, 1999 The Naked Cowboy, aka Robert John Burck, shot into C-list superstardom when he appeared on the Howard Stern show wearing his signature outfit which consisted of a pair of briefs and a guitar. Since then he’s played himself on over 20 television programs and movies, run for the Mayor of New York City, and bid his candidacy for the 2012 Presidential election representing the Tea Party Movement. He owns and operates the Naked Cowboy trademark, too. Not too bad for an entrepreneur who wears nothing but briefs to work every day.

2003: The World Learns About Never-Nudes

Of the many things we took from the short-lived cult comedy Arrested Development, the one thing that continues to be relevant even today is the concept of a “never-nude,” iconically portrayed by character Tobias Fünke. Just like it sounds, never-nude syndrome plays off of gymnophobia (fear of nudity), causing the afflicted to constantly wear an item of clothing to prevent others from seeing their bits. Tobias opted for a pair of too-short denim cutoffs, leading to a number of embarrassing run-ins and inspiring thousands of Halloween costumes that year.

2008: David Beckham Models for Emporio Armani

British Footballer David Beckham reignited the “inappropriately hot underwear model” craze when he signed on to be the face (and body) of Emporio Armani Underwear. Women wanted to get with him and men wanted to be him. From 100-foot-tall billboards to full-page spreads in magazines, Beckham’s perfectly chiseled, tattooed body clad in skimpy, low-rise briefs was everywhere. He was equal parts bad boy and admired athlete, causing a stir not seen since Marky Mark did the same for Calvin Klein almost 20 years earlier.

For more information about these brands: Calvin Klein Underwear, Emporio Armani, Joe Boxer

Photo Credits: Courtesy Photos, Cool Spotters, Fashionist, Emporio Armani, Madonna Fans’ World, Time Inc., The Naked Cowboy, Screened

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