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Ranking the hot hookups of Stephen Dorff

By / 03.11.13

I chose actor Stephen Dorff this week because last week we looked at the alleged dating history of Ryan Phillippe who was married to Reese Witherspoon, who also happened to date Stephen Dorff. Make sense? I also chose to look at the alleged hookup history of Stephen Dorff because, well, it’s a pretty damn impressive list. How impressive? And can he crack the top 10? Maybe, but you’ll have to read on to find out.

Milla Jovovich (1993)


This was so far before the Internet was our source for everything celebrity that there isn’t much/any details here.

Hookup score: 9.0
Once you see the rest of this list, you’ll have no doubt that this actually occurred.

Reese Witherspoon (1994)

Reese Witherspoon

Jenn Deering Davis, Wikimedia Commons


This was pre-Ryan Phillippe, which also means that she was even hotter than when Phillippe locked her down in marriage.

Hookup score: 9.0
Another excellent girl for a guy barely hitting his 20s.

Bridget Hall (1994)


Again we lack Internet access from this time period to get many details, but we have no doubt it happened.

Hookup score: 10.0
As I said before Sports Illustrated swimsuit models are an automatic 10, especially when they’re also former Victoria’s Secret models.

Alicia Silverstone (1994-1995)

Alicia Silverstone

RavenU, Flickr


Alicia and Stephen met while filming Aerosmith’s “Cryin'” music video and was apparently quite the relationship as one outlet said it was filled with “tattoo-getting, cheating, face-punching, suicide-faking, bungee-jumping, and bird-flipping!”

Hookup score: 9.5
This was The Crush – Clueless Alicia Silverstone – big time score.

Georgina Grenville (1995-1996)


Yeah, I’ve never heard of her either but she’s a South African fashion model who once appeared in the always sexy as hell Pirelli calendar.

Hookup score: 9.5
If I had ever heard of her before this might have gotten a 10.

Jessica Alba (1998-1999)


Again really no details, but looking at this list so far, giving him the benefit of the doubt is very easy.

Hookup score: 10.0
It’s Jessica fucking Alba just before Sin City.

Jennifer Love Hewitt (2003)


Not much reported here (but I did find a photo!). Luckily he escaped before J-Love could get him to put one of the three engagement rings she has picked out on her.

Hookup score: 10.0
2003 Jennifer Love Hewitt – it doesn’t get much better.

May Andersen (2003-2004)

May Andersen

david_shankbone, Flickr


New York magazine says that they dated and there are pictures of them together. Best evidence we’ve had so far.

Hookup score: 10.0
Sports Illustrated swimsuit model + party girl = 10.

Shannan Click (2004)


Click and Dorff definitely dated as there are photos to prove it. Dude is on quite a roll here.

Hookup score: 10.0
Sports Illustrated swimsuit model = 10.

Pamela Anderson (2004-2005)


Pam was spotted leaving Dorff’s apartment and they were also seen kissing a few times.

Hookup score: 9.0
The matchup of these two in absolutely no way surprises me.

Sarah Harding (2006)

Sarah Harding

Dell’s Official Flickr Page, Flickr


A couple of reports said that the Girls Aloud singer and Dorff were dating in secret for months.

Hookup score: 9.0
Not a very good secret.

Rachel Stevens (2006)


Well he already dated a British singer from a girl group so why not another?

Hookup score: 8.5
Not as famous, or as sexy.

Tami Donaldson (2007-2008)


She was Miss Maxim 2006. That’s about all I got, but several outlets had them dating for a few months.

Hookup score: 9.0
Miss Maxim is good.

Leilani Dowding (2012)


Page 3 Girl Leilani Dowding and Dorff definitely dated because they broke up in epic fashion with him allegedly sending her threatening text messages.

Hookup score: 8.5
Stephen, please say this was not true. We were really starting to admire you.

Katharina Damm (2012)


Another model I have never heard of before today, Damm and Dorff dated very publicly in 2012. Not sure if this is still a thing or not.

Hookup score: 8.5
Would have been higher if I knew just who the hell she was.

Other less-substantiated alleged flings: Rhea Durham, Kaya Jones, Stacy Sanches, Kristina Shannon, Lela Star

Final Tally

Stephen Dorff’s Hookup Score: 109.5 points

And we have a new entrant in our top five! And being only 39, and slightly saner than Charlie Sheen, I like his chances of moving up at least one more spot before he’s done.

1. Leonardo DiCaprio – 187 points
2. Jack Nicholson – 163
3. Charlie Sheen – 136
4. Stephen Dorff – 109.5
5. Jamie Foxx – 108.5
6. Jared Leto – 108
7. George Clooney – 93
8. Josh Hartnett – 91
9. Chris Evans – 83.5
10t. Justin Timberlake – 82
10t. Ryan Phillippe – 82
12. Orlando Bloom – 81
13. Derek Jeter – 80
14. David Duchovny – 78.5
15. Joe Jonas – 77
16. Ryan Reynolds – 75
17. Ashton Kutcher – 73
18. Jeremy Piven – 72.5
19. Ryan Gosling – 72
20t. Kanye West – 71
20t. Brad Pitt – 71
20t. Jude Law – 71
23t. Colin Farrell – 70
23t. Adam Levine – 70
25. Sean Penn – 69
26. Johnny Depp – 67
27. Jake Gyllenhaal – 66
28t. Tom Brady – 64
28t. Mark Sanchez – 64
30t. Adrien Brody – 63
30t. Adam Brody – 63
30t. Kevin Connolly – 63
33t. Michael Phelps – 62
33t. Adam Duritz – 62
33t. Alexander Skarsgard – 62
33t. Wilmer Valderrama – 62
33t. Gerard Butler – 62
38. Criss Angel – 61
39. John Mayer – 60
40. Bradley Cooper – 57
41. Shia LaBeouf – 56.5
42. Alex Rodriguez – 53
43. Robert Downey, Jr. – 51.5
44. Edward Norton – 51
45. Matthew Morrison – 47


Douglas Charles
About Douglas Charles... Douglas Charles is the co-founder of Guyism.com, now a part of BroBible. 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.
TAGSAlicia SilverstoneAlleged Sexual HistoryBridget Hallcelebrity dating historiesComplete hookup historyGeorgina Grenvillehollywood ladies menJennifer Love HewittJessica AlbaKatharina DammLeilani DowdingMay AndersenMilla JovovichPam AndersonPamela AndersonRachel StevensReese WitherspoonSarah Hardingserial datersShannan ClickStephen DorffStephen Dorff dating historyStephen Dorff girlfriendsTami Donaldsonwho has Stephen Dorff datedwho is Stephen Dorff dating

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