• 2. AMERICA'S SWEETHEART WILL BREAK YOUR HEART photo | Britney Spears, Harry Styles, Justin Timberlake, Taylor Swift

Credit: Lisa Rose/JPI, Tom Meinelt/Splash News Online

Published: Wednesday August 21, 2013 17:00 PM EDT

2013

2. AMERICA'S SWEETHEART WILL BREAK YOUR HEART

When JT, then the face of our collective '90s teenage dream, romanced Britney Spears in 2000, it was a match made in pop music heaven. Until it wasn't, when they split two years later. Here's hoping Styles already got the memo after his swift relationship with the sugarcoated Taylor Swift went sour earlier this year after just a month together.