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Celebrity Breakups Archive - 2000

It's hard to keep a relationship going when you are in the public eye 24/7. The pressures of stardom took their toll on a number of couples in 2000.
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  1. Jennifer Syme and Keanu Reeves

    Jennifer Syme and Keanu Reeves

    32,321 views
    Date Separated: 2000
    Keanu and Jennifer had a daughter together who was stillborn. The pair splits a few weeks after her death, but remained good friends afterwards. Jennifer died in a car accident in 2001.

  2. Eve and Stevie J

    Eve and Stevie J

    29,951 views
    Date Separated: August 2000

  3. Jay-Z and Aaliyah

    Jay-Z and Aaliyah

    22,626 views
    Date Separated: 2000
    Jay-Z once dated Aaliyah, back in 1999. The relationship didn't last. Unfortunately Aaliyah died only 2 years later, at the far-too-young age of 22.

  4. Angelina Jolie and Jenny Shimizu

    Angelina Jolie and Jenny Shimizu

    18,263 views
    Date Separated: 2000
    Jolie and Shimizu dated on and off for many years and Jolie stated on many occasions that she was bi-sexual. "I would probably have married Jenny if I hadn't married my husband. I fell in love with her the first second I saw her," Jolie said.

  5. Shiri Appleby and Jason Behr

    Shiri Appleby and Jason Behr

    15,771 views
    Date Separated: September 2000
    From on screen to off screen during the first season of their show Roswell. To the dismay of many fans he eventually started dating Katherine Heigl during the second season of the show.

  6. Beyoncé Knowles and Lyndell Locke

    Beyoncé Knowles and Lyndell Locke

    14,046 views
    Date Separated: 2000

  7. John Frusciante and Milla Jovovich

    John Frusciante and Milla Jovovich

    11,535 views
    Date Separated: October 2000
    Milla simply adored John, she couldn`t stop telling about how his records profoundly changed her life. John also admired her work as an actress, when they went to see her movie "Joan of Arc" he cried several times. Some say that Milla`s admiration put too much pressure on John, and that he just ...

  8. Macaulay Culkin and Rachel Miner

    Macaulay Culkin and Rachel Miner

    11,212 views
    Date Separated: 2000
    Macaulay Culkin started dating actress Rachel Miner in 1996. The two announced plans to marry, causing a stir over their young ages. They wed in 1998. They separated in 2000 and divorced in 2002.

  9. Bai Ling and Chris Isaak

    Bai Ling and Chris Isaak

    8,680 views
    Date Separated: 2000
    http://www.wireimage.com/search/#events?q=Chris%20Isaak/|Bai%20Ling:201459:SpecificPeople|/[75154324]&ep=1/60/1&s=3

  10. Ben Affleck and Gwyneth Paltrow

    Ben Affleck and Gwyneth Paltrow

    8,515 views
    Date Separated: October 2000
    Gwyneth Paltrow, ex-girlfriend (1998 to 1999) Affleck had a high-profile romance with actress Gwyneth Paltrow in 1998, following her breakup with actor Brad Pitt. ------------------ Paltrow told E! in a special that her relationships with Brad Pitt and Ben Affleck were a bit surreal. "It was strange ...

  11. Jay-Z and Lil' Kim

    Jay-Z and Lil' Kim

    8,272 views
    Date Separated: 2000

  12. Kevin Spacey and Dianne Dreyer

    Kevin Spacey and Dianne Dreyer

    8,100 views
    Date Separated: 2000
    Between 1992 and 2000, Spacey discreetly dated Dianne Dreyer, script supervisor to Anthony Minghella, M. Night Shyamalan and Sydney Pollack.

  13. George Clooney and Lucy Liu

    George Clooney and Lucy Liu

    7,337 views
    Date Separated: 2000
    The two were rumored to date for most of 2000, but no official confirmation was ever issued by either party. The two were caught by paparazzi sharing a steamy New Year`s Eve kiss in 2006.

  14. Winona Ryder and Jimmy Fallon

    Winona Ryder and Jimmy Fallon

    6,994 views
    Date Separated: 2000
    Who: Jimmy Fallon What: Funny valentines from 2000-01 Winona tried a new type of man -- the comedian -- when she hooked up with Jimmy Fallon, who was only a few seasons into his run on "Saturday Night Live" at the time. We guess things didn't end too badly, because they looked like they ...

  15. Anne Heche and Ellen DeGeneres

    Anne Heche and Ellen DeGeneres

    6,855 views
    Date Separated: August 2000
    Anne and Ellen were together for three years. Heche's same-sex relationship with comedienne Ellen DeGeneres and the events following their breakup became subjects of widespread media interest. The couple started dating in 1997, and at one point, said they would get a civil union if such became legal ...

  16. Nina Hartley and Bobby Lilly

    Nina Hartley and Bobby Lilly

    6,324 views
    Date Separated: 2000

  17. Beck Hansen and Leigh Limon

    Beck Hansen and Leigh Limon

    6,295 views
    Date Separated: 2000

  18. Rebecca Budig and Daniel Geller

    Rebecca Budig and Daniel Geller

    6,275 views
    Date Separated: 2000
    (1 June 2000 - October 2000) (divorced)

  19. Matt Damon and Winona Ryder

    Matt Damon and Winona Ryder

    5,471 views
    Date Separated: August 2000
    The two were a high-profile couple while together -- 'People' magazine declared them "Hollywood's It Couple" -- despite both their efforts to keep it from the public eye. "There's no advantage to putting it into public consciousness," Damon told GQ in 1999. "It's ...

  20. Oscar De La Hoya and Shanna Moakler

    Oscar De La Hoya and Shanna Moakler

    5,365 views
    Date Separated: September 2000
    Moakler started dating boxer Oscar de la Hoya in October 1997 and they moved in together in early 1998. Moakler and de la Hoya became engaged prior to the 1999 birth of their daughter, Atiana Cecilia de la Hoya (born March 29, 1999). Moakler has said "it wasn’t a planned pregnancy, but it was ...

  21. Yasmine Bleeth and Richard Grieco

    Yasmine Bleeth and Richard Grieco

    5,299 views
    Date Separated: February 2000
    Yasmine and Richard met on the set while filming "Heaven or Vegas". Before the end of their first week together, they were inseperable. They dated between 1996-1997, then got back together again between 1998-2000. They had an on-again, off-again relationship that was hindered by her involvement ...

  22. Nick Carter and Willa Ford

    Nick Carter and Willa Ford

    5,266 views
    Date Separated: 2000

  23. Houston and Brad Parascandolo

    Houston and Brad Parascandolo

    4,984 views
    Date Separated: 2000
    Prom boy & porn star still a duo Their sensational high school swan song has evolved into an enduring relationship of 14 months that saw Brad Parascandolo bolt to his prom queen`s home in LA. In fact, it`s been rumored that wedding bells may ring for the notorious "odd couple."

  24. Ryan Reynolds and Kristen Johnston

    Ryan Reynolds and Kristen Johnston

    4,596 views
    Date Separated: January 2000

  25. Robin Givens and Howard Stern

    Robin Givens and Howard Stern

    4,514 views
    Date Separated: April 2000

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