Restart slideshow

The Most Daring Dresses Ever Worn At The Grammy Awards

1. Jennifer Lopez In Versace, 2000
In 2000, Jennifer Lopez made history when she appeared at the Grammys wearing her now-iconic Versace dress. The dress was so popular that it literally invented Google Images — people couldn't stop looking up the dress, so Google decided to make a page that aggregated all of the photos together. 
In the debut episode of Lopez's new YouTube series, “Moments of Fashion," the artist recalled the experience of picking out the sheer gown and how unprepared she was for the media's reaction. Lopez remembered that she was nominated for a Grammy that night, but all month long she was tied up with shooting scenes for her upcoming movie, The Wedding Planner, so she didn't have time to try on dresses.

Since Lopez waited until the last possible minute to choose her dress (the day before!) her stylist, Andrea Lieberman, had only three to four gowns to choose from.

"Usually if you come to a fitting of mine, there are tons of dresses and tons of shoes. There's always so many choices. But this day we only really had a choice between two dresses," Lopez shared in the video. “One was kind of like a white dress and the other was the Versace jungle-print dress.”

Her stylist urged Lopez to choose the white one because the Versace piece had already been worn by three other people — including Donatella Versace herself. She decided to go with her gut, though, and chose the sheer number. 

When Lopez arrived at the Grammys, there was a group of people blocking the entrance to the red carpet. But when she stepped out in her Versace, she recalled that there was a kind of sweeping murmur through the area and the crowd began to part for her. She had no idea it was because of her gown.

“It was a frenzy," she said in the video. "The flashes started going in a way that it’s not usually. There was an extra kinetic energy there. I was like what the hell is going on? I had no idea it was about this dress.” It finally clicked for her when she went on stage to present an award, and her gown got a standing ovation. From that moment on, history was made.