6. Whitney Houston and Bobby Brown

This love story lasted 14 years but ended up tragic, with both substance abuse and domestic abuse. At first, Houston turned down Brown’s marriage proposal because she didn’t want to get married at the time. But in 1992, the two wed, and the following relationship ended a decade later. 

7. Drew Barrymore and Luke Wilson

Quirky redhead Drew Barrymore has been Hollywood’s sweetheart for decades, and the handsome Luke Wilson began a romantic relationship with her after they filmed the 1997 movie “Home Fries.” After dating for a couple of years, they broke up before “Charlie’s Angels” was filmed, but they still had to work together — awkward!

8. Kurt Cobain and Courtney Love

This rocker couple had a controversial relationship in the eyes of the media and the public, especially since Love still used illegal substances when she was pregnant. In 1994, the romance abruptly ended when Kurt took his own life, but they’re still known as the ultimate grunge romance. 

9. Bruce Willis and Demi Moore

Once a power couple of the 90s, Bruce Willis and Demi Moore remained married until 2000. At that point, they had three kids but remained on good terms post-divorce. Willis even attended Demi and Ashton’s wedding in 2005.

10. Winona Ryder and Matt Damon

After spending two years in a relationship, Ryder and Damon experienced a public breakup. Apparently, the two were introduced by Gwyneth Paltrow, who was dating Damon’s BFF, Ben Affleck, at the time.