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.
Christina Applegate and Brad Pitt
In the '80s, Brad Pitt and Christina Applegate were (like many well-known stars at the time) in the spring of their careers. Pitt just started to walk through the path of fame, and Applegate was breaking through with her role in "Married With Children." These two were friends as teenagers.
Pitt (together with other future stars such as Jason Priestly) would come to her parent's house for Sunday lunches. Pitt was even her date to the 1989 MTV Movie Awards, though she left with someone else… awkward! They both went on to other partners eventually, though. Applegate is now married to musician Martyn LeNoble, and Pitt, well... we all know what happened with him.
Christine Taylor and Neil Patrick Harris
Dr. Doogie Howser is not all a goody two shoes. Way before he came out and revealed to the world his orientation, he dated actress Christine Taylor. She is best known and loved for her role in "The Brady Bunch" and in "The Wedding Singer." They dated from 1997 until 1998. A relationship that lasted just over a year.
They were a relatively private and quiet couple, with not too many horror stories to make the paparazzi's day. These days, Doogie is happily married to David Burtka, and Christine is married to Ben Stiller, also in a very happy way.
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.
Winona Ryder and Matt Damon
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.