Top 10 Hottest Women Chris Brown Has Hooked Up With

Chris Brown stays busy.  Though his career seems to go through highs and lows of attention and anonymity, his fame has afforded him the ability to woo a lot of amazing and impressive women.

Everyone knows about Chris Brown's big relationships.  His relationship with Rihanna has been on-again, off-again for over a decade now, and it seems he's officially ended his chances with his latest partner, Karrueche Tran, after public fights and alleged infidelity.  Given his dating track record, including a long list of infidelities, public scenes, verbal abuse, and even physical assault, no one would be surprised if Karrueche were escaping another poor relationship.

Brown is, unsurprisingly, not so much the relationship type.  He reports more hookups and "casual relationships" than he does serious relationships or committed partnerships.  Maybe this is due to personal preference, a psychological qualm, or maybe he just hasn't found "the one" yet.  In any case, he certainly has managed to find a plethora of other women willing to be with him that are impressive in their physique, careers, and backgrounds.

So here they are!  The 10 hottest women Chris Brown has hooked up with.

10 Draya Michele


Seriously, Draya Michele is killing it. She's a star on the reality television show Basketball Wives LA. She's been on previous seasons because of her engagement to Orlando Scandrick, a cornerback for the Dallas Cowboys (why is the fiancee of a football player on a basketball wives show? Who knows, no one can make sense of it).

9 Nia Gonzalez

[caption id="" align="alignnone" width="634"] via[/caption]

You might also know her by her preferred name, Nia Amey. Amey is the name she goes under when working professionally in her modelling career, most of which are nudes or minimal coverage shots.

She might have just began as a hookup for Chris Brown. It seems that the two never really tried to make a go at a relationship. However, it would seem that they weren't very careful either. Nia is now Chris Brown's "baby mama," for lack of a better term. Nia seems to be working her way through college. While playing mother to his child, she's also a nursing school student and works two jobs. She's a hardworking woman and a single mother. She's independent and doesn't let anyone boss her around.

8 Simply Jess

[caption id="" align="alignnone" width="2500"] via[/caption]

Who's that, you're asking? Simply Jess is the self-proclaimed best promoter of arts events in the Miami area. If you visit her twitter page, which you can find here, you'll see that she stays incredibly busy. Barack Obama followers her. I mean... what? Who the hell is this chick?

She and Chris never formally committed themselves to a relationship, but they dated on and off and hooked up many times between 2010 and 2012. The two still hang out occasionally; if nothing else, they've maintained a great business relationship.

7 Natalie Nunn


Natalie was a cast member of the reality television show Bad Girls Club during its fourth season and has since appeared on a handful of other reality shows, playing a shallow, confident, sassy version of herself.  She's married to Jacob Payne (an Arizona Rattlers football player) now, but she's had a handful of interesting courtiers in her time including Wiz Khalifa, Rorrey Fenty (Rihanna's brother, if you can believe that weird bit of irony), and, of course, Chris Brown.

6 Amber Rose


Amber Rose (her real name is Amber Levonchuck) is a model, fashion designer, and actress.  You might have seen her in Black-ish, Selfie, or The Hills, and she's got a role in Zoolander 2.  Her career had tragic beginnings: she stripped to provide for her family after her parents divorced.  She was soon discovered, though, and her career took off, ensuring her family would never go without again.

Amber is, without argument, a gorgeous woman: she's curvy, voluptuous, and is well endowed both in front and behind.  She's had her share of famous romantic partners: Kanye West, Machine Gun Kelly, Wiz Khalifa (with whom she married and mothered a child), and Chris Brown.

5 Jasmine Sanders

[caption id="" align="alignnone" width="1274"] via[/caption]

Jasmine is super hot, but that's not what makes her awesome.  She's made herself a career out of nothing, and she's not going to let anything get in her way.

German born and South Carolina raised, Jasmine is a model second, internet personality first.  Her instagram has over 1.3 million followers.  This baby-faced starlet knows how to climb to the top and she's "becoming a top model on her own terms," inspiring everyone else in her field.

4 Natalie Mejia


Natalie was a member of a pop group called Girlicious.  The group was a sort of spin-off of The Pussycat Dolls.  They created the same basic product: albums of women selling sex through shallow lyrics.  She's a self-managed singer, model, dancer, and "actress" (not really though, her only acting experience is playing herself on reality TV), though she hasn't had nearly as much success since Girlicious disbanded in 2011.

3 Keisha Kimball


Can we bring Baywatch back so Keisha can star in it?  Keisha is a model and actress (though her acting career is definitely eclipsed by her modeling career, and rightfully so as she's not very good).  While she does a lot of swimsuit and underwear modeling, she prefers to sport bohemian styles in her personal time.

2 Rhea

[caption id="" align="alignnone" width="525"] via[/caption]

Rhea is a singer who was a part of Pharrell William's crew, N.E.R.D. (standing for No-one Ever Really Dies. She was kicked out because her sound didn't match the rest of the group).  She's one of the backup singers you hear in all of Pharrell's songs.  A native of Guyana and raised in Canada, she's got an interesting upbringing.  She's got a lot of talent and a lot of spunk, which may be a couple of the reasons Chris Brown was interested in her.

1 Anara Atanes


Yeah, it makes sense that Chris Brown would want to wake up every morning to see her.  She's a British pop singer and a Victoria's Secret model (no surprises there).  She's known by paparazzi and online because of her foul mouth and lack of self-censoring.  She's deeply passionate about Futbol (soccer, for you Americans that can't get with it) and has been banned from multiple matches for poor behavior (you know how raucous you have to be to get banned from those?).

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Most Popular

Top 10 Hottest Women Chris Brown Has Hooked Up With