Oh sure, now he’s all tied down with Angelina Jolie and her brood, but it wasn’t always that way for former Sexiest Man in the World, Brad Pitt. At several points along the way he was the most eligible bachelor in the world, and he took advantage. But where does his alleged dating history rank him amongst the greats? Read on to find out.
Photo: YouTube
Robin Givens (1986-1987)
Seeing Givens with Pitt turned Mike Tyson from a hardcore tough guy to a fly on the wall. “It just totally overwhelmed me,” said Tyson, “I had no energy to fight.”
Hookup score: 8.5
An extra half a point for being so cool that even Mike Tyson had to stand down.
Photo: YouTube
Christina Applegate (1989)
Dated briefly during her early run on Married With Children. Just two kids having a good time.
Hookup score: 10.0
Wouldn’t be a 10 now, but during year two of MWC? Brad was The Man.
Photo: YouTube
Juliette Lewis (1991-1993)
Pitt and Lewis worked together on Too Young to Die? and Kalifornia. She was 10 years younger than him. He was 26. She later claimed he has a tiny penis.
Hookup score: 6.5
She was pretty famous and all, but damn, the tiny penis thing….that’s not good.
Photo: YouTube
Thandie Newton (1994)
Newton and Pitt met on the set of Interview with a Vampire. (Beginning to see a trend developing?) Not much fun happened here. Moving on.
Hookup score: 8.5
Strong rebound effort.
Photo: YouTube
Gwyneth Paltrow (1994-1997)
Paltrow was his co-star in the movie Seven. (Did I mention a trend?) They even went so far as to get engaged, but as we all know it didn’t last. Perhaps one of the seven deadly sins reared it’s ugly head and caused the break-up.
Hookup score: 8.5
Almost three years with Gwyneth Paltrow. That’s gotta earn him half a bonus point.
Photo: YouTube
Demi Moore (1998)
Reportedly spent time together in the waning days of Demi and Bruce Willis’ marriage.
Hookup score: 9.0
This would have been easily as fun to watch as Demi and Ashton if only it had lasted.
Photo: YouTube
Jennifer Aniston (1998-2005)
We’re all very well-versed in this one, right? They dated for two years, got married, were the ideal Hollywood couple. Five years later she filed for divorce. That’s right. She filed.
Hookup score: 10.0
They did look really pretty together.
Photo: YouTube
Angelina Jolie (2005-Present)
Surely you know how these two met, right? Why, she was his co-star in the film Mr. & Mrs. Smith! Of course she was. Three months after Pitt and Aniston’s divorce was finalized Jolie announced she was pregnant. Perhaps now we know why Jennifer filed those papers.
Hookup score: 10.0
Brad went from being a part of the perfect Hollywood couple with one woman directly to the same title with another one. Well done, sir.
Other less-substantiated alleged flings: Elizabeth Daily, Geena Davis, Claire Forlani
Photo: YouTube
Final Tally
Brad Pitt’s Hookup Score: 71 points
That puts Brad in a tie for the 12th spot. And we had such high hopes for him during the early years. Too many engagements and marriages weighed the score down though.
1. Leonardo DiCaprio – 187 points
2. Jack Nicholson – 163
3. Charlie Sheen – 136
4. George Clooney – 93
5. Josh Hartnett – 91
6. Justin Timberlake – 82
7. Orlando Bloom – 81
8. Derek Jeter – 80
9. Joe Jonas – 77
10. Ryan Reynolds – 75
11. Ryan Gosling – 72
12t. Kanye West – 71
12t. Brad Pitt – 71
14t. Colin Farrell – 70
14t. Adam Levine – 70
16. Sean Penn – 69
17. Johnny Depp – 67
18. Jake Gyllenhaal – 66
19t. Alexander Skarsgard – 62
19t. Wilmer Valderrama – 62
19t. Gerard Butler – 62
22. John Mayer – 60
23. Bradley Cooper – 57
24. Edward Norton – 51
(Photos: Aniston, Applegate, Givens, Jolie, Lewis, Moore, Newton, Paltrow, Pitt)