Before NSYNC became NSYNC, the pop girl group Wild Orchid was a big thing, and Justin Timberlake and Fergie had it going. They were both in the entertainment industry from a young age, which is probably what drew them to one another. Timberlake was just 16 years old, and Fergie was seven years his senior.
Age was never a barrier until Britney came along. They have since both had high-profile relationships. Fergie married actor Josh Duhamel, had a son with him, and then the two got divorced. Timberlake is currently married to actress Jessica Biel, and they now share two kids.
John Cusack and Lili Taylor
John Cusack and Lili Taylor starred together on "Say Anything." As it turns out, Taylor wasn't satisfied with only dating Cusack, as it was reported that she had a bit on the side with D.V. DeVincentis, one of Cusack's best friends at the time. Though they probably didn't stay friends after that.
In 2000 Taylor and Cusack starred together again, this time in the movie "High Fidelity." How ironic, considering how their previous relationship ended. The affair between the two never skyrocket, and maybe that's a good thing when you think about the uncomfortable events that made them go their separate ways in the first place.
Liam Neeson and Helen Mirren
This might come as a shock to you, but during the 1980s, the queen of the Oscars dated the king of the screen for almost five long years. Neeson and Mirren met playing the roles of Gawain and Morgana on the set of "Excalibur" when they were still both unknown.
They lived together, loved one another deeply, and admitted that, at the time, they were considered a serious item. Mirren confessed that the two broke up because Liam had difficulty being under Helen's shadow. If only he would have realized that such a great actor could never be under anyone's shadow.
Charlie Sheen and Robin Wright
Notoriously a bad boy, every single relationship that Charlie Sheen has been involved in reached the tabloids and the headlines. Except for one. Not much is known about his short affair with Robin Wright, and we are here to tell you all about it.
Sheen and Write had a sweet teenage romance that went on from 1981 until 1982. Sheen was 16, Write was 15, and they two were both in high school. This obviously explains why the press wasn't in on it when the two were an item. Since then, the two have dated many other Hollywood stars, enough to fill up another list.
Juliette Lewis and Brad Pitt
Before he became an A-lister, before his Hollywood royalty days, and before "Thelma and Louise," Pitt dated his co-star at the time, Juliette Lewis. She starred alongside him in "Too Young to Die?" and they were together for just over four years, despite a significant age difference between them.
In 1993 the couple decided to go their separate ways. They had an innocent love affair that would probably never survived if they would have met at an older age. Lewis married (and divorced) professional skateboarder Steve Berra, and Brad became Brad Pitt and had a lot of women to date.