Ranking the hot hookups of Usher

Usher dating history girlfriends

Usher image by Helga Esteb/Shutterstock


Usher, full name Usher Raymond IV, is another one of those singers out there whose alleged dating history we’re curious about. Let’s see who he’s supposedly hooked up with over the years, shall we? Surely ladies the world over would like to get their hands on a handsome, wealthy singer, right? Of course, but how many of them have been sexy famous celebrities? Read on to find out.

Photo credit: Usher image by Helga Esteb/Shutterstock

Monica Arnold (1995)

Monica Arnold

Monica Arnold image by Jaguar PS/Shutterstock


Usher and Monica dated when they were teens.

Hookup score: 8.0
Isn’t that sweet? Young love.

Photo credit: Monica Arnold image by Jaguar PS/Shutterstock

Brandy Norwood (1998-1999)

Brandy Norwood Usher

Brandy Norwood image by s_bukley/Shutterstock


While nothing was ever officially announced, there appears to be a pretty good chance these two dated at some point.

Hookup score: 8.5
Good enough to count.

Photo credit: Brandy Norwood image by s_bukley/Shutterstock

Karrine Steffans (2000)

Karine Steffans Usher

Karrine Steffans image by Featureflash/Shutterstock


We only know that Karrine Steffans and Usher allegedly hooked up (at least according to her), but we’re not sure about whether they actually dated.

Hookup score: 8.0
Hooked up, dated, whatever, it counts.

Photo credit: Karrine Steffans image by Featureflash/Shutterstock

Rozonda ‘Chilli’ Thomas (2001-2004)

Rozonda Chilli Thomas

Rozonda Thomas image by Featureflash/Shutterstock


Usher and “Chilli” were quite the musical couple for three years until they broke up right before he released his album Confessions.

Hookup score: 8.5
Confessions, huh? Something you’re not telling us, Usher?

Photo credit: Rozonda Thomas image by Featureflash/Shutterstock

Naomi Campbell (2004)

Naomi Campbell Usher

Naomi Campbell image by Featureflash/Shutterstock


Usher and supermodel Naomi Campbell dated for a few months until things went awry either because “he was bored” or because “his entourage was too controlling.”

Hookup score: 10.0
Seems like kind of an odd pairing anyway.

Photo credit: Naomi Campbell image by Featureflash/Shutterstock

Joy Bryant (2005)

Joy Bryant Usher

Joy Bryant image by Joe Seer/Shutterstock


Not a lot of great evidence here to support the fact that actress Joy Bryant and Usher ever were a thing other than a couple of spotty reports.

Hookup score: 8.5
Half a point downgrade for lack of clarity.

Photo credit: Joy Bryant image by Joe Seer/Shutterstock

Pamela Anderson (2006-2007)

Pam Anderson Usher

Pamela Anderson image by s_bukley/Shutterstock


Pamela Anderson basically admitted crushing on Usher and rumors persisted that they were dating. Alas, she denied them. (As these celebs seem to always do.)

Hookup score: 8.5
Lot of smoke here, and when there’s smoke…there are unsubstantiated rumors! Half a point downgrade.

Photo credit: Pamela Anderson image by s_bukley/Shutterstock

Kim Kardashian (2009)

Kim Kardashian Usher

Kim Kardashian image by Helga Esteb/Shutterstock


According to Usher’s former bodyguard he and KimKSuperstar hooked up on a few occasions in the past.

Hookup score: 9.0
If you can’t believe a former bodyguard who can you believe?

Other less-substantiated alleged flings: Jessica White

Photo credit: Kim Kardashian image by Helga Esteb/Shutterstock

Final Tally

Usher’s Hookup Score: 69 points

Kind of disappointing. Usher’s 35 years-old and has been at it since 1987. Of course he was married for several years in there which brought his score down a little.

1. Leonardo DiCaprio – 187 points
2. Jack Nicholson – 163
3. Charlie Sheen – 136
4. Bruce Willis – 120
5. Tommy Lee – 111
6. Sean ‘Diddy’ Combs – 110
7. Stephen Dorff – 109.5
8. Jamie Foxx – 108.5
9. Jared Leto – 108
10. Vin Diesel – 100.5
11. Cristiano Ronaldo – 99.5
12. Russell Brand – 99
13. Seth MacFarlane – 98
14. Tiger Woods – 93.5
15. George Clooney – 93
16. Tom Cruise – 92.5
17t. Benicio Del Toro – 91
17t. Josh Hartnett – 91
19. Drake – 88
20. Chris Evans – 83.5
21t. Justin Timberlake – 82
21t. Ryan Phillippe – 82
21t. Tyson Beckford – 82
24t. Ben Affleck – 81
24t. Orlando Bloom – 81
26t. Josh Hutcherson – 80
26t. Tyrese Gibson – 80
26t. Derek Jeter – 80
29t. David Duchovny – 78.5
29t. Marilyn Manson – 78.5
31t. Jim Carrey – 77.5
31t. Owen Wilson – 77.5
33. Joe Jonas – 77
34. Ryan Reynolds – 75
35. Ashton Kutcher – 73
36t. Harry Styles – 72.5
36t. Jeremy Piven – 72.5
38. Ryan Gosling – 72
39t. Kanye West – 71
39t. Brad Pitt – 71
39t. Jude Law – 71
42t. Colin Farrell – 70
42t. Adam Levine – 70
44t. Usher – 69

44t. Sean Penn – 69
46t. Taylor Lautner – 67
46t. Johnny Depp – 67
48t. Ian Somerhalder – 66.0
48t. Jake Gyllenhaal – 66
50. Andy Roddick – 64.5
51t. Tom Brady – 64

51t. Mark Sanchez – 64
51t. Joseph Gordon-Levitt – 63
54t. Zac Efron – 63
54t. Adrien Brody – 63
54t. Adam Brody – 63
54t. Kevin Connolly – 63
58. Chris Pine – 62.5
59t. Michael Phelps – 62
59t. Adam Duritz – 62
59t. Alexander Skarsgard – 62
59t. Wilmer Valderrama – 62
59t. Gerard Butler – 62
64. Liam Neeson – 61.5
65. Criss Angel – 61
66. John Mayer – 60
67. Bradley Cooper – 57
68. Shia LaBeouf – 56.5
69t. James Franco – 53
69t. Alex Rodriguez – 53
71. Will Smith – 52
72. Robert Downey, Jr. – 51.5
73. Edward Norton – 51
74. Paul Walker – 48.5
75. Matthew Morrison – 47