24 Forgotten Celebrity Couples Of The 90s

The decade where Neil Patrick Harris dated a woman and Jodi Foster dated a man.

1. Madonna & Vanilla Ice

Apparently they split when Madonna published photos of them having sex in one of her books.

2. Johnny Depp & Kate Moss

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.

4. Drew Barrymore & Ed Norton

5. Sandra Bullock & Matthew McConaughey

6. Halle Berry and Danny Wood

In 1990, before she was an Oscar winner, Halle was “Hangin Tough” with the lead singer of NKOTB.

7. Matthew Perry & Julia Roberts


8. Neil Patrick Harris & Christine Taylor

Probably no chance they’ll be getting back together.

9. Nicholas Cage & Patricia Arquette

10. Conan O’Brien & Lisa Kudrow

11. Courtney Cox & Michael Keaton

Michael’s face says it all really.

12. Mila Kunis & Macaulay Culkin

13. Julia Roberts & Kiefer Sutherland

14. Brad Pitt & Christina Applegate

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.

17. Ryan Gosling & Sandra Bullock

18. Kathy Griffin & Jack Black

19. Gary Oldman & Uma Thurman

These two were actually married in the early 90s.

20. Meg Ryan & Russell Crowe

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.

23. Topher Grace & Anne Hathaway

24. Russell Crowe & Jodie Foster

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