1. Madonna & Vanilla Ice
Apparently they split when Madonna published photos of them having sex in one of her books.
3. Leonardo DiCaprio & Liv Tyler
Neither of them really age, so really this photo could have been taken yesterday. But no, the pair dated for a year in the late 90s.
6. Halle Berry and Danny Wood
In 1990, before she was an Oscar winner, Halle was “Hangin Tough” with the lead singer of NKOTB.
8. Neil Patrick Harris & Christine Taylor
Probably no chance they’ll be getting back together.
11. Courtney Cox & Michael Keaton
Michael’s face says it all really.
12. Mila Kunis & Macaulay Culkin
15. Sarah Jessica Parker & Robert Downey Jr.
That neck tie…
16. Sofia Coppola & Keanu Reeves
Apparently they met when her father directed Keanu in 1992’s Dracula . Creepy.
19. Gary Oldman & Uma Thurman
These two were actually married in the early 90s.
21. Whoopi Goldberg & Ted Danson
It all ended when he showed up in black face at a Friars Club Roast…
22. R. Kelly & Aaliyah
These two actually got married in the 90s… but because Aaliyah was 15, the marriage had to be annulled.
- Iran's parliament approved a deal on its nuclear program, which was agreed in July following lengthy talks between six world powers. ›