Sometimes in life, all you need is a best friend to introduce you to their partner’s best friend, and there you go. You get yourself a boyfriend. In the late 1990s’, Gwyneth Paltrow was Winona Ryder’s best friend. Paltrow was also dating Ben Affleck. Matt Damon was Affleck’s best friend and you can see where this is going.
The two hit it off and a match was made. Damon and Ryder dated for over three years and were known as Hollywood’s hottest couple back then. Matt Damon quickly moved on to his next story in life, and Winona Ryder wasn’t left far behind.
Robert Downey Jr. and Sarah Jessica Parker
Way back in the 1980s, Robert Downay Jr. was still unknown for his roles as "Iron man" in the MCU. In fact, he was so out of it with his substance dependency that it seems that Sara Jessica Parker came just in time to put him back on his feet.
The two were filming a movie together, ending in a seven-year relationship. Downey found it hard to let go of his former lifestyle, which was difficult for Parker to handle. Since then, he has left his mark in "Chaplin" and "Sherlock Holmes," and Parker has left us wondering whatever happened to Mr. Big and the City.
Lisa Marie Presley and Michael Jackson
This is about as good as it gets. The King of Pop dated the King of Rock n Roll's daughter. AKA the Rock n Roll princess. The early 1990s were the days when everything was about Michael Jackson's legal accusations, and Lisa Marie managed to make the wind blow in a different way.
Lisa Marie even famously starred in Jackson's music video for his ballad "You Are Not Alone". They were married for under two years and had no children together, yet they managed to preserve their titles, which they both left as their legacy following each of their deaths.
Elle Macpherson and Billy Joel
Apparently, you don't have to be the best-looking guy in the class to date the most beautiful girl around. Well, that's how it was back in the 1980s'. Back then, the known and loved "Piano Man" was (and still is) a successful musician and one of the best-selling artists of all time.
During those days, Joel started to date Elle Macpherson, who back then was (and still is) a beautiful model making her way through law school (though that law part was only true for about a year). The two dated for a short time and then decided to go their own way.
Courtney Love and Edward Norton
Courtney Love's most famous relationship was and will always be the one she had with the late Kurt Cobain but this entry is about a different relationship. The movie "The People vs. Larry Flynt" is where it all began. Norton and Love co-starred and started to date shortly after. They dated for over four years, which turned them into a well-known couple in the Hollywood scene.
Like all couples, they had their ups and downs. However, their downs seemed to make the headlines way too often. In 1999, Courtney Love practically ditched Edward in the middle of a fight and never returned.