1999 was a much simpler time. Brad and Jen. Julia and Ben(jamin Bratt). Teenage films starring actual teenagers topping the box office. Without the addition of reality television and internet celebrities, movie stars were the biggest names covering the pages of tabloids and MTV’s TRL was a must-hit stop for anyone wanting to make an impact on an audience under 30. Before the onslaught of reality star sex tapes and power couple portmanteau, Julia Roberts was just a girl, dating a Law and Order hunk and Nicole Kidman was still married to Tom Cruise. (Pause for laughs.)
Before the year 2000 high school flicks like American Pie proved just as valuable at the box office as boy bands and a new Latin wave were to album sales. Brad Pitt had split from Gwyneth Paltrow, who rebounded with Ben Affleck. And because this was prior to GOOP or conscious uncoupling, we all teared up a little bit when that big slab of pink fabric accepted her Oscar for Shakespeare in Love. Drew Barrymore was a Hollywood success story, overcoming a tumultuous childhood career and reaching the height of her adorable flower child phase with hit after hit. Bouncing from romances with Serious Actor Edward Norton to professional goofball Tom Green was considered endearing, not flaky. Britney Spears made school uniforms naughty, opening the floodgates for a year of teen pop that even your mother would admit to finding hummable. And no one had Snapchat.
Because we love celebrities so much the thought of a lasting relationship between Carson Daly and Jennifer Love Hewitt keeps us up at night, check out the 20 biggest stars from the year 1999. Sure, the fashion was ridiculous, but that’s because we all thought we were going to die on January 1, 2000.
How well do you know some of the biggest hits of 1999? Take TLC’s quiz and find out.
[Photo Credit: Getty Images]