Bras are at once a girl's best friend and her worst enemy. Empowering and sexy but sometimes cumbersome and awkward, the bra has long been linked to women's rights, feminine identity, and, yes, boobs of all kinds. History's also heaving with events where the brassiere has taken center-stage, but since the birth of the bra goes back to BC, we've compiled a list of modern moments—like Jane Curtin's infamous on-air (and apparently, imageless otherwise we'd have featured it—rats!) statement of her own sexiness for boob-tube favorite, Saturday Night Live. Sexy, epochal, and, oh yeah, silly, these intimates did way more than just keep the girls in place!
1) Madonna's Gaultier Cones
With two extremely perky Bugles covering her already perfectly formed ladies, the now-infamous Gaultier number was—if you can believe it—inspired by Gaultier's grandmother. Like the seriously hardcore Victorian corsets of Nanna Gaultier's past, the centerpiece of the Blonde Ambition tour pays homage to ladythings of lore, but warned showgoers to not look too close lest they poke an eye out.
2) Princess Leia's Captive Bra
The holy grail of nerdy sexpots, Princess Leia (and more specifically, the captive Princes Leia) steamed up the already muggy cave of Jabba the Hut with a metallic bra and matching loincloth.
3) The Push-Up Wonderbra
Advertised to "lift and separate" (do we really want the latter?), the first Wonderbra was born in the '30s, but it wasn't until the '60s that the push-up model was introduced.
4) Mrs. Robinson in The Graduate
We've never attempted bribing anyone by flashing our brassiere (at least to our very sober recollections), but if we ever did, we'd re-watch the famous Anne Bancroft scene where the seductive Mrs. Robinson gets naughty in her Playtex.
6) Lil' Kim's Parading Pasty
As an exercise on liberal definitions, Lil' Kim's "bra" bounced and jiggled onto screen during the 1999 MTV Music Video Awards causing Diana Ross to give her squeeze of approval and a nation of television viewers' jaws to drop straight to the ground.
5) Susan Sarandon in The Rocky Horror Picture Show
We've been to countless Rocky Horror Picture Show sing-a-longs, but no two-bit Susan Sarandon can mimic the subtle sexiness of Janet's simple, white bra. Pure genius!
7) Britney's Rolling Stone Cover
The then 17-year-old Britney had a lot to show for herself on her first magazine cover where, in pigtails and her iconic schoolgirl garb, she finally let the buttons—and her innocence—go. The rest, as they say, is history.
8) Victoria's Secret 10-Million-Dollar Bra
Every year, Victoria's Secret releases a Fantasy bra that looks like it dropped out of Elizabeth Taylor's jewelry box; Covered entirely with diamonds, rubies, and other precious stones, each version is custom-designed by some of the best known jewelers in the business.
9) Brandi Chastain's Sports Bra
Soccer-star Brandi Chastain's game-winning kick in the 1999 Women's World Cup gave the sports bra back its moment in the sun (literally). Why should guys hog all the whipping-my-victory-shirt-off fun?
10) Janet Jackson's Nipple Snafu
We can't be sure if Janet's starburst nipple ring was a bra or not, but her inadvertent flashing at the hands of grab-happy Justin Timberlake might have been the best story of the bra that never was.
11) The Seinfeld Bro
Sometimes, the guys need a little support, too. An invention for Seinfeld's Frank Costanza, The Bro (or Manssiere, if you will) provided that extra bit of male security for Frank's extra bits of man.
