Sure, these famous couples are impossible. But let’s imagine they could be.

Anna Nicole Smith and John F. Kennedy

1

Brad Pitt and Veronica Lake

2

Catherine Zeta Jones and Robert Vaughn

3

Demi Moore and Paul Newman

4

Marlon Brando and Penelope Cruz

5

Kirk Douglas and Halle Berry

6

Gary Cooper and Scarlett Johansson

7

George Clooney and Grace Kelly

8

Elvis and Angelina Jolie

9

Ann Margret and Tom Cruise

10

Bernie Mac and Billie Holiday

11

Vanilla Ice and Veronica Lake

12

Gary Busey and Sally Eilers

13

Paul Newman and Scarlett Johansson

14

Gregory Peck and Jessica Simpson

15

Gwen Stefani and Charlie Chaplin

16

Elizabeth Hurley and Clark Gable

17

Marilyn Manson and Audrey Hepburn

18

Clark Gable and Kelly Clarkson

19

Buster Keaton and Tara Reid

20

Humphrey Bogart and Drew Barrymore

21