See what the children of famous couples from the ’90s and early ’00s would have looked like…

Even if a celebrity couple does not remain together indefinitely, their relationships can have a lasting influence on their admirers. However, many renowned couples who were supposed to be inseparable split up and never had children together in the last few decades.

1. Jennifer Lopez and Ben Affleck

2. Johnny Depp and Kate Moss

3. Cameron Diaz and Matt Dillon

4. Jake Gyllenhaal and Kirsten Dunst

5. Winona Ryder and Matt Damon

6. Drew Barrymore and Luke Wilson

7. Leonardo DiCaprio and Gisele Bündchen

8. Brad Pitt and Gwyneth Paltrow

9. Cindy Crawford and Richard Gere

10. Matthew McConaughey and Sandra Bullock

11. Justin Timberlake and Britney Spears

12. Jessica Biel and Chris Evans

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