Chilli Rolls Out

Posted on April 25th, 2008 - By Bossip Staff

Categories: Chilli, News, Usher

Posted by Bossip Staff

Chili Rollin Out

Here is Chilli on the cover of Rolling Out this month not looking a day over 19. She’s looking good and we’re especially happy that someone did her hair for this photoshoot and left out all that damn babyhair.

Chili Rollin Out 3Chili Rollin Out 4Chili Rollin Out 5

View more pics of Usher’s pre-Tameka boo and a special treat right about now

Chili Rollin Out 2Chili Rollin Out 1usher’s new promo pic

rollingout.com

  • rox

    1st…on a lame roll today! chilli looks good!

  • SWEET CHEEKS

    SHE’S GOREGOUS!!!!!!

  • NIKKI UNDERWOOD

    Thank the Lord she does not have that same do!!! Get it Chill :)

  • NIKKI UNDERWOOD

    USHER….SICK and throwing up in his mouth like it is his first trimester :(

  • Gutter

    She owns the copy rigts to having baby hair.

  • http://myspace.com/afiya00 Afiya

    Chilli is just too damn cute.

    Tomboy is going to all the stores in the neighborhood and burning every mag so Usher can’t reminise.

    :lol:

  • getyourhandouttamypocket

    Chilli looks great! Gon’ girl!

  • da darkness

    k ms. tickness. girl better keep on eatn that chilli. lol hello ush like damn look what i did

  • Slick selebrity

    who sits and a cheap a** slip covered IKEA sofa for a photoshot, Hey girl I got a camera you want me to take your picture in my dorm room.

  • da darkness

    r.i.p. lisa “left eye” lopez EYE miss you

  • HOTSTUFF

    Nice!!

  • http://www.myspace.com/msmeka2cute Mz_Magnificent1

    Damn these older chicks are killin the game…go ‘head Chilli!!!

  • rox

    slick…..i don’t think anyone’s looking @ all that….chilli’s got us all just staring at her?!

  • NIKKI UNDERWOOD

    getyourhandouttamypocket….

    Where have you been? MIAO?

  • $m♥K.E.Y.

    A Classic Beauty

    A day over 19? okay let’s not push the envelope

    how about a day over 21, that makes sense, and is believable

    NO BABY HAIRS, HOO-RAHHH!

  • $m♥K.E.Y.

    SWEET CHEEKS

    SHE’S GOREGOUS!!!!!!

    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

    NAH YOUR GRAVIE IS GORGEOUS! PRAISE-EM’

  • Gutter

    Shes way hotter then Beyonce

    Stans get mad.

  • http://www.myspace.com/shamecatierrajackson ms meca

    she is very pretty

  • getyourhandouttamypocket

    NIKKI UNDERWOOD

    getyourhandouttamypocket….

    Where have you been? MIAO?

    ——————

    Just busy chile….

  • mojojojo195

    GOOD MORNING

    HELLO TO EVERYONE

  • free

    slick, lmao. i was thinking the same thing but i guess she gotta start somewhere….

  • Lady Architect

    She looks very nice in these shots. Usher better not get this mag or hide it so Tameka won’t see it.

  • Ydatzy

    I aint gay but damn.

  • Suga Mo

    Usher looks like he is about to go out to the garage and tune up chilli car. They sis make a nice looking couple. She is so pretty.

  • Suga Mo

    They MADE a nice looking couple

  • mojojojo195

    THE COPS WHO SHOOT SEAN BELL GOT OFF!!

    THEY SHOT THIS UNARMED MAN 52X AND THEY GOT OFF

    I AM SO UPSET RIGHT NOW

  • guilty pleasure

    She looks great!

    And…….I’m loving these shoes!!!!!!!!!!!

  • Cage

    Usher stopped dealin with her after he found out she was a Death Row groupie…. A straight up jumpoff… The whole TLC was.. I’d still smash though she lookin hot…

  • Eye

    I wonder if those are the shoes that Floyd Mayweather bought her…….

  • COME ON

    usher is very happy with the one he’s with, he had chili didn’t want her and moved on plain and simple. look’s isn’t everything especially in usher and a of other folks book when it comes to your love. “IF YOU JUST BASE YOUR RELATIONSHIP ON GOOD LOOKS- YOU WOULD BE LOOKING ALLWAYS BECAUSE, THEIR WILL BE SOMEONE THAT LOOK’S BETTER- THAT REAL TALK.

  • Keepin’ It Real (D’Original)

    Nice…

    Beautiful smile, legs lookin’ real GOOD…

  • Frog-a-licious

    She looks pretty.

  • REAL TALK

    IN response to (COME ON) AKA TAMEKA! Don’t be jealous. .. looks aren’t everything, but, Come On Chilli damn sure got you beat. Maybe has no choice but to be with the one he’s with, especially when the one he had has moved on. And, yes there is always someone who looks better; however, he didn’t get better, or good. Don’t be mad!

  • Frog-a-licious

    And that promo pic of Usher looks good too.

  • I’m Just Me

    SHE IS SO PRETTY!! THIS IS A GOOD LOOK FOR HER. HER AND STACY DASH ARE AGING WELL! :)

  • ATLBlogger

    Yes, the girl does look good for her age and she DO be killing the babyhair! And I’m loving those shoes in that 3rd pic.

  • Crazy Ass Rodney

    She’s cute in a flat chested midget sort of way

  • Encyclopedia Brown

    At what point do we stop saying baby hair? Isn’t Chili 40 years old?

  • Lovely One

    She’s always been pretty. Look at the pic with her in the car (THOSE SHOES ARE HOT!)

  • Shandy

    She’s pretty, but man…….she is almost like a dwarf lol.

  • ????

    How the hell does Usher go from her to Maneka????

  • soulwoman

    Chilli looks great!

  • http://www.myspace.com/ocky_j Octavia

    I swear… sistas age WELL!!! :-)

  • Sharie

    Absolutley gorgeous. No other words for her… What the hell was Usher thinking?

  • Jessica

    It is really beautiful, I will share it with my friends I knew on the FREE luxury +c.e.l.e.b.r.i.t.y +m.i.l.l.i.o.n.a.i.r.e +d.a.t.i.n.g. +s.i.t.e ++++ r.i.c.h.m.a.t.c.h.m.a.k.i.n.g …c o m++++. . I will post it to my blog.

  • lusciouslipps

    Chili looks great & doesn’t seem to age at all.

  • Chi-city

    Chilli is Beautiful, she always has been,she doesn’t look a day older than when TLC first came out. Whether Usher is sick or not you have to admit him a Chilli were a good looking couple, they looked so happy together, and I for one would love to see them together again someday

  • REAL2REELVISIONS

    Chilli looks caliente.

    Check out this artist

    http://www.myspace.com/egocartelmusic

  • BLUNTBLAZER

    19 NAW MAYBE 23 BUT STILL GOOD

    http://WWW.MYSPACE.COM/THAGRINDAHOLIC

    NUHTIN BUT THAT GHETTO KNOCK

  • ES 300

    I saw Chili at Lenox about a week ago…she looks just a good in person and the booty is NICE, real NICE, but damn she is short!

  • T-Bird

    Chili is looking beautiful…the extra pounds look good on her…she is positively glowing…no doubt a CD has to be coming out soon. You go girl…This is definitely refreshing…I’m tired of the Stacy Dash booty shot magazine covers.

  • oliver

    Every time I signed in __ Bigblackconnect.com __ and there were always many women would talk to me … It is a funny and interesting place to talk to these thoughtful women.

  • Torion

    Chilli looks beautiful as she always does. She and Ursher were truly a beautiful couple. They should’ve never split. He aint been the same since.

  • I Don’t follow I Lead

    Very nice photos, very attractive young woman. I love the shoes in the pic with her sitting in the car.

  • Dominique=Maxwell Fan♥

    THat’s My Celebrity Twin!

    Do your Thang Girl!

  • JAD

    SHE IS GORGEOUS……

  • Wenzel Dashington

    I wish she would move next door :)

  • Brooklyn, Stand UP!

    Usher is a retard for letting this one go.

  • Kosigned

    Chilli is bangin in those pics, Chilli and Stacy Dash making 40 the new 20.

  • Brie

    oh YES- usher owns that promo pic… mmm…

  • William Powers

    Dayum she look good.

  • Zina {The original princess}

    @ sins of the heart;

    Who the hell is Ursher?

    Anywho, these photos look so cheap to me, she might have well went to Magic Photo. I hate the airbrushing on her upclose pic and makeup and tired ass poses. She’s a pretty girl but the photog needs a well deserving “ho, sit down”!

  • BooBoo

    stopp TALKING BOUT WHAT SHE DID IN THE PAST, uSHER PROBABLY WAS HOEING 2!! tHE GIRL LOOKS GOOD AND SHE ONLY GOT 1 KID AND USHERS WIFE GOT WHAT 4??? SO WHO WAS GIVING BOOTY AWAY/? HMMM

  • Tracey

    Is it my eye, why does her head look extra big in these pictures?

  • Hodge Podge

    She looks nice, but the camera angle iis terrible on the 1st picture. She looks too damn compact!!

  • http://YAHOO DIAMOND

    CHILI KNOWS SHE’S A NICE LOOKING OLDER LADY. USHER HATIN RIGHT NOW CAUSE HE MARRIED A MUDDD DUCKKK….. FROM THE PROJECTS WHO DID HIS HAIR TO TIGHT.

  • baeyaki

    yay Chili…girl you are beautiful!!!

  • no no no

    now that she has that baby-hair in check, she can stop screwing other women’s husbands.

  • Not Today

    Usher had a bad ass girl!!

  • Me

    Go Chilli. Do your thang!!!

  • asil

    stop hating usher was probaly cheating too, she deserves better too, and she looks better than these young hoes dont hate

  • fab!

    She is 39/40 and looking really good!usher…WHY!!!!!

    She is so much prettier than that porch-monkey! Tameka either knows VOO-DOO or her cooch has a magic door wrapped in velvet!

  • AlessandraJordan

    ahahahaha. USHER must feel like a damn FOOL right now!

  • tameka raymondnot usher wife lol

    YOU ARE DIEAD WORNG TO PUT USHER PIC RIGHT NEXT TO HIS EX LOL USHER LOOKED GOOD . AND CHILLI NEED TO RETREIED WHO WONT TO HEAR HER SING IS BEYOND ME SHE CANT SING SHE WAY BETTER WITH TLC. SHE FINNLEY GOT RIDE OF THOSE BABY HAIR BUT AM SURE SHE WILL PUT THEM BACK AGIAN THATS HER STREAD MARK.

  • WESTCOASTLOVE

    TAMEKA GOT THAT MUFFU@@A 2

    MARRY HER ASS AND CUT HIS CONTROLIN ASS MOMMAS WATER OFF SOOOOOOOO TAMEKAS HOLDIN IT DOWN WHEN IT COMES TO THAT ONE OKKKKKKKKKKKKKKKKKKKKKKKKKKKKK ~NOW ….

    WHO HAS CHILI MARRIED ? DOESNT

    SHE HAVE A SON BY UMMMMMM WHATS HIS NAME DALLAS

    AUSTIN WHO LOOKS LIKE HE COULD EASILY BE REV.

    RUNS SON DIGGY’S DAD!!!!!

    LOL AINT HE THE SAME MUFFU@@A THAT ROBBED T,L.C I THINK SOOO MAYBE THATS WHY LEFT EYE WASNT F@CKIN WIT HER BEFORE SHE DIED HHMMMM , SHES VERY PRETTY BUT I BET HER WALLS ARE BLOWN OUT F@KIN WIT THEM DEATHROW NI@@AS….. WESTCOAST ON MINES OOOO AND SHE KAINT SING AT ALL

  • WESTCOASTLOVE

    NEVA COULD ~

  • cookie

    CHILLI IS VERY PRETTY AND A NICE PERSON. CHILLI AND USHER TRY’D TO MAKE IT WORK. ALL CHILLI WANT’D TO DO WAS MARRIE, LOVE, RESPECT,AND HAVE USHER CHILDREN . WHAT’S WRONG WITH THAT . USHER SAID THAT HE LOVE’S CHILLI AND SHE WAS HIS HART . JUST TRY TO BE FIRENDS. OH USHER GOING TO BE A FATHER AGAIN. GO BLESS THE 2 OF U

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