Side Chicks: The Hall of Fame Edition

November 29, 2011  |  
1 of 8

The 2012 Republican presidential candidate pool is such a circus it reminds us more of a terrible reality show rather than suitable contenders for the highest office in the land. Enters Herman Cain, former CEO of Godfather Pizza, an alleged serial sexual harasser of women and apparently a philanderer. Herman’s latest “awe jeez not this Shyte again moment” came yesterday from his alleged mistress of 13 years, Ginger White. Ginger has outed Herman for his cheating ways, and by the time you read this she will probably have given a tell-all interview to Fox News. Said interview will be a serious blow to the Republicans coveted “black man,” who up until now has been pretty steady in the polls. For the record, Ginger is a racially ambiguous woman (some say she might be a fair-skinned black woman, not that it matters like THAT), which bodes well for Uncle Herman because we all know white America would flip their wig if Cain was sticking his hand in the prized cookie jar of Southern white women.

But enough about Herman Cain and his side show antics! His new blunder got me to thinking about how many men have been taken down by their notable side chicks, mistresses, jump offs — call them what you may. Who are some of the more standout mistresses that we’ve seen over the years? I took to my Twitter feed, asked around, and learned one thing very quickly: I better not put Alicia Keys or Gabrielle Union on this list, so I will tread lightly when talking about those young women, who are doing great things for the community might I add! Take a walk with me down the side chick hall of fame; you’ll see some familiar faces and some not so familiar ones, but they all have something in common: creeping with somebody else’s man.

Barbara Walters

Number one on my list of notable side chicks is Barbara Walters and not because her relationship was super public or because she made her career based on being someone’s friend with benefits. No, Barbara Walters makes the list off of the sheer principle that no one believed she was the side-boo of Senator Edward Brooke when she announced it as a part of her recent memoir. For one, it’s Barbara Walters; she’s not typically the woman you think is running around getting fresh with a U.S. Senator. But think about the ramifications of a sitting senator, a black senator at that, having an affair with a top journo back in the day (the ’70s). It’s something out of the movies! She gets notable side chick status from me for being so good at keeping it on the hush for so long. 

Angelina Jolie

One of my real life friends on Twitter said it best: “Angelina Jolie is the ultimate side chick…she got Brad to divorce his wife and adopt her adopted kids without marrying him.” Now that’s cold blooded, and that’s something out of one of those pimp books from back in the ’70s. Angelina Jolie is like Sunshine from Harlem Nights, she threw that thing in Brad’s face and he called Jennifer and told her he wasn’t never coming home. Now that’s P-Power.

Ashley Alexandra Dupré

I want to give a special shout out to the call girl turned media superstar, Ashley Dupré, who ousted former Governor of NY, Eliot Spitzer, from his post as the King of New York. Some say Eliot was on his way to the White House, and that he had that much political clout at the time Miss Dupré called him out. Ashley is now a sex columnist for the New York Post and apparently she sings too. She makes the list because she not only dethroned a prominent politician headed for the White House, but she made some money off it too. Can’t knock the hustle!

Monica Lewinsky

I feel sorry for Monica Lewinsky in a way. How would you feel if your sole reputation rested on the fact that you were going down on President Bill Clinton and allowing him to insert cigars into…nevermind.  Notable side chick nonetheless, her and that blue dress are infamous. She might also go down as being famous for being a little demented; it’s not everyday that a woman keeps the dress someone “spilled” semen on. How did she get out of the White House with smeared seminal fluid on her dress!? I guess that’s something only an oracle can answer. Monica you’re on the list but by far we’re still laughing at you, not with you.

Ashanti and Fantasia

Now I know the complexion of this list has been a little pale so before I’m accused of rallying against white women who play the mistress role, allow me to throw some black women under the bus as well (kidding…kind of). Now, Ashanti and Fantasia have to share the spotlight because I don’t think either of them have enough star power currently to deserve their own page about their transgressions. Ashanti we kind of felt sorry for. Don’t get me wrong, she was messing with a woman’s husband (Irv Gotti), but she was young, naive and new to the music business. It seems she’s been on the straight and narrow path ever since then, so we can’t throw too much shade her way (plus, she’s from Long Island). But Fantasia, we can’t get jiggy with that mess you pulled with that good, middle class woman’s husband. Then tried to portray yourself as the victim and get suicidal like you weren’t breaking up a happy home. If you ask me, the person who lost the most out of all this, outside of the child, is the man, Antoine Cook.  His wife was good looking and now he’s stuck with Fantasia–that’s gotta hurt!

Karrine “Superhead” Steffans

Superhead needs no introduction–she single-handedly aired out the whole music industry in one fell swoop. From Irv and Ja to Shaq, Jay-Z and Diddy, no celebrity went untouched. Even allegedly Method Man (supposedly Big Papa). Karrine is the worst kind of side chick: the type who runs and tells your lady! What part of the game is that? So what, they stopped giving you money after you wore yourself out and you thought you’d exact some revenge? You mad?  But once again, we can’t knock her money hustle, because Karrine went on to become a New York Times Bestseller writer and even found herself a short bid as a wife, married to Eddie Winslow. Congrats Karrine, you are a notable side chick of many men!

Anne Boleyn

There are too many side chicks and not enough pages but I will give two of them a quick honorable mention; Leanne Rimes, and Marilyn Monroe. But for the ultimate side chick I want to take it back to the 1500’s and give a shout out to the former Queen of England, Anne Boleyn. Born of humble means, Anne ascended from a mere mistress to the Queen of England, bestowing upon her heirs the kingdom of England. Now that’s a rag to riches story for you. She’s credited with helping start the English Reformation and most of all, she died for this ish. She was beheaded on trumped up charges of treason, adultery and incest, but she lives on now as a martyr and a heroine of England. Long live the Queen.

Who did I miss? Tell us your candidates for the hall of fame of side chicks!

Email nativenotes at or follow him on Facebook/Twitter/Tumblr and check out some his writings over at Notes of This Native Son

More on Madame Noire!

Trending on MadameNoire

View Comments
Comment Disclaimer: Comments that contain profane or derogatory language, video links or exceed 200 words will require approval by a moderator before appearing in the comment section. XOXO-MN
  • Toni Xing Wanliss

    This list crack me up and has me Shocked at the same time..Barb Walters>>>OMG ///fave side chick from this list…Anne Boelyn

  • Pingback: Side Piece: The Hall of Fame Edition | HitHost.Org()

  • Observant Guest

    How soon we forget. Why are we so scared to mention Jada Pinkett-Smith. She did the exact same thing that Angelina Jolie did back in the day. Or don’t we remember that?

  • Pingback: Famous Celeb Mistresses | Z 107.9()

  • Pingback: Famous Celeb Mistresses | 93.1 WZAK()

  • Pingback: Famous Celeb Mistresses | WERE-AM 1490()

  • African

    Add Avonte “Cherie” Wright – mistress to Boyz II Men’s Shawn Stockman for 9 years, even before he was married. Poor thing! I found that out because she was on Tough Love Miami.

    Props to having Anne Boelyn on the list!

  • Theresa

    You forgot the queen Alicia Keys

  • Korey

    Nice shout out to Anna Boelyn there.

  • 123

    “Then tried to portray yourself as the victim and get suicidal like you weren’t breaking up a happy home.”
    There are only two people who can break up a home: the two people in the relationship. If it truly was a “happy home” no other wo/man could come in between a strong couple. 

  • Sntwwatkins

    Anne Boleyn was not from humble beginnings! Her father was an Earl and a Diplomat!  She was a commoner because she was not of noble blood, but she was still a wealthy aristocrat.  Where did you get your info??

  • Thetruth

    The fact that Fantasia cant even read is sad by its self….just on that fact alone dude already lost.

  • CJ

    Why? Who told you not to throw Alicia Keys on this list. Puleeeasssseee!!!

  • Maybe Imma a little ghetto

    Hold up native notes I’m tired of people jumping on Fantasia when Alicia Keys did the same d*** thing.  She shoulda had her own page up there. I don’t care if Alicia got more money and more star power than ‘Tasia from High Point, NC.  Right is right and wrong is wrong.  So if you calling out one call out the other.  A garden utensil is a garden utensil no matter what the price tag on it.  

  • Maybe Imma a little ghetto

    Hold up native notes I’m tired of people jumping on Fantasia when Alicia Keys did the same d*** thing.  She shoulda had her own page up there. I don’t care if Alicia got more money and more star power than ‘Tasia from High Point, NC.  Right is right and wrong is wrong.  So if you calling out one call out the other.  A garden utensil is a garden utensil no matter what the price tag on it.  

    • I was being funny which is why I kept mentioning both Keys and Union, you probably missed the piece that I dedicated squarely to Keys and called her a homewrecker. 

  • Girliusmaximus

    So what if they’re doing things for the community. IF they were doing the “thug dizzle”, you should have put them on here… Sounds like someone is SCARY CAT.

  • Tonya

    Great article! Well done.

  • Brittrodg

    You forgot about Alicia Keys (respected singer-songwriter turned home wrecker), Elizabeth Taylor (home wrecker), Kat Stacks (jump-off),Cassie (model, singer?, jump-off), Kimbella ?( jump-off who “happened” to get pregnant), Whoopi Goldberg (home wrecker)….I’m sure there’s more.

  • Clarkash3

    I guess everyone is gonna go burn their bras and become all feminist because of this post. lol Made me chuckle… Good job nativenotes!

    • Thanks Clarkash3 laughing is contagious. Much love!

  • guest

    Ok, you are laughing at Monica Lewinsky, not Bill Clinton, but Herman Cain is a clown to you?  Right.

  • guest

    Ashley Dupre wasn’t Spitzer’s side chick.  Get your facts right.  She was a call girl at the prostetion ring he frequented.  She ultimately led to Client no. 9’s downfall, but she wasn’t his sidechick.

  • guest

    It never ceases to amaze me how Cain is always the whipping boy for Liberal Black America.  None of these allegations have been proven to be true. Furthermore, in the case of the blonde woman whom is represented by Gloria Allred, what she alleges were crimes.  Why no charges 13 years ago?  And let’s not forget the number one serial cheater, Bill Clinton whom I’m sure is a hero to the author, Nativenotes.  Finally, why are we leaving Alicia Keyes and Gabrielle Union off the list?  They were creeping with other women’s men after all.  So what if they do “great things”?  I am sure the women whose men they stile do equally great things as well…’s just not publicized because they are not in the limelight.

  • IJS

    Ok, the most infamous HOES of them all (Alicia Keys & Gabby Union) didn’t make the list but you put Fantasia made it???? She honestly didn’t know and he said he lied!!  Who wrote this story? You’re on my list. smh.

    • guest

      I couldn’t agree more!  Supposedly Keys and Union didn’t make the list becuase of all the “good” things they do in the community… if that matters.  What goes around, comes around.  Word is that Gabby gets cheated on constantly.  As for Keys, it’s just a matter of time.

  • ay

    “I better not put Alicia Keys or Gabrielle Union on this list, so I will tread lightly when talking about those young women, who are doing great things for the community might I add!”

    is this shade?……

    • IJS

      Not enough cus she’s not calling them the homewreckers that they are.

      • Veratta Pegram-Floyd

        I respectfully disagree with calling both Alicia Keys and Gabrielle Union “homewreckers”. IMO, in order to wreck a home, a home has to have (and/or maintain) a stable foundation to begin with. Let’s look at the facts:

        In Key’s case: Swizz stepped out on his marriage to Mashonda AT LEAST once. Not too long ago, he was DNA tested by some international producer. He is now the father of a 3-5 year old daughter with this woman. To go off on a tangent for a bit, Mashonda put the business out there. I understand that she is the victim but there is a better way to act when kids are involved. Not only that, she put Keys on blast but didn’t put this other woman on blast. Why put one on blast and not the other? Is it because one is in the public eye and you want that fame too? Hmmm.

        In Union’s case: That home was a wreck. Siovaughn (D. Wade’s ex wife) alleged many allegations against D during the divorce proceedings, one was of him cheating on her and giving her an STD. When the truth came out, it was actually that Siovaughn had been cheating and brought the STD home to D. This does not mean that he was not cheating, let’s just be clear. Additionally, Siovaughn’s lawyers kept dropping her, she repeatedly would not show up for court, and she ultimately lost custody of her kids. When have we ever seen the woman not be granted custody, especially when it is a major ball player with a crazy schedule…that should tell you a whole lot right there.

        I want it to be clear that I don’t think these women were in the right. They should have waited until these men were completely single. I don’t care about GU one way or the other but my opinion of A.Keys was lowered a bit because I see great things for her and I don’t agree with her getting caught up with a man who already has a bunch of kids. I do agree that they were mistresses (in Key’s situation, now a wife), but I feel that the term homewrecker needs to be re-examined for both of their situations.

        Additionally, as women, especially as BLACK WOMEN, there needs to be more sista solidarity. Let’s keep it real, neither one of these women were married nor had commitments with other individuals. It was the men out here getting with these women. Why are we always pointing fingers at the one who isn’t in the committed relationship?

        • ay

          somebody with sense!

  • Darkman

    Barbara Walter?! WAOW I thank her for her discretion, even if here career was at risk. She’s probably not the only one to date a secret black man (Hi, Sarah).

    A famous hidden relationship, even it wasn’t really a side chick: Kim Novak and Sammy Davis Jr.

    I think Marylin IS the ultimate side chick: dating 2 married brothers at the same time, who can best that?

    How about an article on hidden relationship (one being black of course)? Open the closet!!!

  • F3ral Anarchy

    go head barbara walters gettin her some black snake moan :OD

  • Guest24

    Hey mom when I grow up I want to be man’s side chick not his Queen but his side chick.

  • Rud

    terrible topic for an article, of all the things to write about..why this? its bad enough that MN is even noting these women for this, but to almost glorify it is reprehensible….

  • Gaylyn

    Ashanti and Irv Gotti??  I didn’t know about that one.  Honestly, I can’t put the two of them together in that way.

    • guest

      I knew about this from his reality show on VH1 a few years back…..Gotti’s Way.  The wife mentioned it.

  • superfly78

    *in my Kandi’s mom’s voice”This is some bull sh#t!”

  • ishouldbestudying

    the guys are losers too.

  • ishouldbestudying

    you make this sound like it’s a good thing

  • Samlawson6787

    Great article and not many know about Anne Boylen so good job taking it back!!

    • i’m the magnificent

      this article is stupid. grammy winning artists ashanti and fantasia aren’t ‘famous enough’ to be on this illustrious list by themselves and are insulted for their looks, but an effing white PROSTITUTE gets props for being a ho. yeah okay, madame noire is whack to the 30th degree.

    • Sugar_Spice

      Or her skanky sister Mary Boleyn!

  • IllyPhilly

    Yall throw Black women under the bus all the time MN. CTFU @ Jolie though. See that’s woman not after a ring and not desperate to have somebody on her arms. she “offered” that a$$ and got a loyal man at that!

    • IJS

      Shoot, I want to know what she’s working with to turn Brad into an “Occupy Wallstreet” lookalike. She needs to write a book. Poor Brad hasn’t been the same since. lol 

    • Jezebel Ai

      Angelina Jolie was not the side-chick type, so don’t use her as an example. She is the exception that proves the rule. But this is the kind of -ish women tell themselves that lets them overlook the fact that a man is married, living with someone else, or someone else’s boyfriend.