Ranking the hot hookups of Ryan Phillippe

david_shankbone, Flickr

I thought that since we saw Reese Witherspoon at the Oscars last weekend looking as sexy as ever that this week we’d take a look at the alleged dating history of her ex-husband Ryan Phillippe. Yep, that’s all it takes to pique my interest. Now we know that Ryan Phillippe had enough game to lock up Reese at least for a little while, but how has he fared pre- and post-Reese when it comes to scoring with the pretty and famous? Read on to find out.

Photo credit: david_shankbone, Flickr

Reese Witherspoon (1997-2006)

Jenn Deering Davis, Wikimedia Commons

They met at Reese’s 21st birthday party, got engaged, starred in Cruel Intentions together, had two kids – a boy and a girl – and got divorced. End of story.

Hookup score: 9.0
She’s still a little hottie now, but this was back in her prime.

Photo credit: Jenn Deering Davis, Wikimedia Commons

Nikki Reed (2007)

david_shankbone, Flickr

Reed and Phillippe were spotted on a date when he was 32 and she was 18. Playa.

Hookup score: 9.0
Perhaps the sexiest actress from the Twilight films.

Photo credit: david_shankbone, Flickr

Abbie Cornish (2007-2010)

Eva Rinaldi, Wikimedia Commons

Cornish met Phillippe on the set of the film Stop-Loss. Yeah I never heard of it either, but it produced an almost three-year relationship so it’s got that going for it.

Hookup score: 8.5
Highly underrated.

Photo credit: Eva Rinaldi, Wikimedia Commons

Lindsay Lohan (2010)


A “pal” of Lohan’s said that they “definitely hooked up.” A second “friend” of LiLo says they hooked up again later that same week.

Hookup score: 8.5
Of course she’s on this list.

Photo credit: YouTube/Harper’s Bazaar

Jessica White (2010)

david_shankbone, Flickr

White and Phillippe were spotted leaving a Saturday Night Live afterparty together. Good enough!

Hookup score:10.0
Sports Illustrated swimsuit models (current and former) are an automatic 10.

Photo credit: david_shankbone, Flickr

Alexis Knapp (2010)

Tom Sorensen, Wikimedia Commons

Alexis and Ryan dated throughout the summer of 2010, then it was reported that she was pregnant and she had his baby well after they had broken up.

Hookup score: 9.0
I had to look her up. She’s quite sexy.

Photo credit: Tom Sorensen, Wikimedia Commons

Amanda Seyfried (2010-2011)


Phillippe and Seyfried met at Kate Hudson’s Halloween party (don’t we all) and dated for about six months before calling it quits.

Hookup score: 9.5
Also highly underrated.

Photo credit: YouTube/Glamour

Rihanna (2010)


“Sources” said that Rihanna and Phillippe were hooking up for a few months, being “very casual” and “discreet.”

Hookup score: 9.5
The only way to go. At least he didn’t knock her up.

Photo credit: YouTube/Rihanna

Ashley Greene (2011)


Reports said that Greene and Phillippe hooked up, but they denied it – standard procedure. After seeing the rest of the names on this list we’re going to give him the benefit of the doubt here.

Hookup score: 9.0
Perhaps the sexiest actress from the Twilight films.

Other less-substantiated alleged flings: Ashlee Simpson, Demi Lovato.

Photo credit: YouTube/Esquire

Final Tally

Ryan Phillippe’s Hookup Score: 82 points

Well there weren’t any famous women pre-Reese, but post-Reese dude has been on a roll, tied for 9th place. Impressive since I can’t remember the last time he was in a movie I watched.

1. Leonardo DiCaprio – 187 points
2. Jack Nicholson – 163
3. Charlie Sheen – 136
4. Jamie Foxx – 108.5
5. Jared Leto – 108
6. George Clooney – 93
7. Josh Hartnett – 91
8. Chris Evans – 83.5
9t. Justin Timberlake – 82
9t. Ryan Phillippe – 82
11. Orlando Bloom – 81
12. Derek Jeter – 80
13. David Duchovny – 78.5
14. Joe Jonas – 77
15. Ryan Reynolds – 75
16. Ashton Kutcher – 73
17. Jeremy Piven – 72.5
18. Ryan Gosling – 72
19t. Kanye West – 71
19t. Brad Pitt – 71
19t. Jude Law – 71
22t. Colin Farrell – 70
22t. Adam Levine – 70
24. Sean Penn – 69
25. Johnny Depp – 67
26. Jake Gyllenhaal – 66
27t. Tom Brady – 64
27t. Mark Sanchez – 64
29t. Adrien Brody – 63
29t. Adam Brody – 63
29t. Kevin Connolly – 63
32t. Michael Phelps – 62
32t. Adam Duritz – 62
32t. Alexander Skarsgard – 62
32t. Wilmer Valderrama – 62
32t. Gerard Butler – 62
37. Criss Angel – 61
38. John Mayer – 60
39. Bradley Cooper – 57
40. Shia LaBeouf – 56.5
41. Alex Rodriguez – 53
42. Robert Downey, Jr. – 51.5
43. Edward Norton – 51
44. Matthew Morrison – 47