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Ranking the hot hookups of Robert Downey, Jr.

By / 10.29.12
Robert Downey dating history girlfriends

<a href="" target="_blank">YouTube/Marvel</a>

With all the news coming out last week about Iron Man 3, I thought today would be a good day to take a look at the alleged dating history of the film’s superstar Robert Downey, Jr. Granted he’s happily married now, but that wasn’t always the case. Earlier in his career he was just your typical male Hollywood star and that means access to female Hollywood stars. So how does Tony Stark stack up against the other ladies men we’ve chronicled? Read on to find out.

Photo credit: YouTube/Marvel

Jennifer Jason Leigh (Date unclear)

jennifer jason leigh

<a href="" target="_blank">YouTube/Universal Pictures</a>

There’s no real information available on this relationship because it happened pre-Internet, but Wikipedia says that she was romantically linked to Downey, and that’s never wrong is it?

Hookup score: 8.5
She was a pretty big star after Fast Times at Ridgemont High. Score would have been higher had it been Phoebe Cates though.

Photo credit: YouTube/Universal Pictures

Sarah Jessica Parker (1984-1991)

Sarah Jessica Parker

<a href="" target="_blank">YouTube/New Line Cinema</a>

No disputing this one as Downey and Parker were together for about seven years after meeting on the set of the film Firstborn.

Hookup score: 8.5
This was obviously pre-Sex and the City so bonus points for that.

Photo credit: YouTube/New Line Cinema

Winona Ryder (1988)

Winona Ryder

<a href="" target="_blank">YouTube/Lionsgate</a>

There is practically nothing on the Internet about this one other than the year it supposedly took place so it may not have ever happened.

Hookup score: 8.0
So annoying that the Internet wasn’t around in 1988 to help confirm/deny this. I’m guessing it didn’t happen, so it gets a downgrade.

Photo credit: YouTube/Lionsgate

Deborah Falconer (1992-2001)

Downey and singer/actress/model Deborah Falconer got married after dating for just 42 days. Unfortunately, this was at the height of Downey’s personal issues pretty much dooming the relationship. They have one child together

Hookup score: 9.0
She was pretty good-looking, which explains why she was a model, so good for him.

Photo credit: Tumblr

Marisa Tomei (1992, 1994)

marisa tomei

<a href="" target="_blank">YouTube/Fox Searchlight</a>

Tomei and Downey were reported to be a couple while starring together in the movie Chaplin and were rumored to be more than friends once again after appearing together in the film Only You.

Hookup score: 9.5
What can we say. We loves us some Marisa Tomei and this was right around the time of her Oscar win.

Photo credit: YouTube/Fox Searchlight

Calista Flockhart (2000)

Calista Flockhart

<a href="" target="_blank">YouTube/MGM</a>

Flockhart and Downey allegedly spent a lot of time flirting as he made a guest appearance on Flockhart’s TV show Ally McBeal. He even reportedly brought her flowers and sweets on the set.

Hookup score: 8.0
Sounds like a lot of nothing, but we’ll count it.

Other less-substantiated alleged flings: Farrah Fawcett

Photo credit: YouTube/MGM

Final Tally

Robert Downey, Jr.’s Hookup Score: 51.5 points

Well, he only beats out Edward Norton on our list, but that’s to be expected since both of them have been married for quite some time. Looks like Iron Man is for the most part also a One-Woman Man. (And his resume is still better than yours or mine will ever be.)

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

12t. Jude Law – 71

15t. Colin Farrell – 70

15t. Adam Levine – 70

17. Sean Penn – 69

18. Johnny Depp – 67

19. Jake Gyllenhaal – 66

20. Mark Sanchez – 64

21t. Alexander Skarsgard – 62

21t. Wilmer Valderrama – 62

21t. Gerard Butler – 62

24. Criss Angel – 61

25. John Mayer – 60

26. Bradley Cooper – 57

27. Alex Rodriguez – 53

28. Robert Downey, Jr. – 51.5

29. Edward Norton – 51

TAGSAlleged Sexual HistoryCalista FlockhartComplete hookup historyDeborah FalconerJennifer Jason LeighMarisa TomeiRobert Downey JrRobert Downey Jr girlfriendsSarah Jessica Parkerserial daterswho has Robert Downey Jr datedwho is Robert Downey Jr datingWinona Ryder
Douglas Charles
About Douglas Charles... Douglas Charles is the managing editor of His experience includes operating an assortment sports and entertainment Web sites over the past decade, but his specialty is discovering sexy women from all over the world that he knows he will never have a chance with, let alone meet - a quality he shares with 99.99% of his readers.

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