>> Stephen: WELCOME BACK, EVERYBODY!
FOLKS, MY NEXT GUEST WENT FROM CREATING A YOUTUBE SERIES
ABOUT HER LIFE TO CREATING AN HBO SERIES ABOUT HER LIFE.
PLEASE WELCOME, THE STAR OF "INSECURE," ISSA RAE!
( CHEERS AND APPLAUSE ) ( BAND PLAYING )
HI.
NICE TO MEET YOU.
>> YOU GOT ME THROUGH COLLEGE.
>> Stephen: DID I?
YEAH, I GAVE YOU MY DIPLOMA BUT I NEVER PICKED IT UP.
>> Stephen: YOU CAN CLEAR SOMETHING UP FOR ME.
I HAVE A QUESTION ABOUT YOU.
THAT IS YOU HAD A POPULAR YOUTUBE SERIES CALLED "THE
MISADVENTURES OF AWKWARD BLACK GIRL."
>> YES.
>> Stephen: YOU SEEM LIKE A SELF-POSSESSED AFRICAN-AMERICAN
WOMAN.
WHAT MAKES YOU AN AWKWARD BLACK GIRL?
>> JUST LIFE.
FEELING UNCOMFORTABLE AT ALL TIMES.
I GREW UP IN PREDOMINANTLY WHITE NEIGHBORS AND --
>> Stephen: ME, TOO.
I CAN UNDERSTAND.
>> I'M AFRICAN AND IT WAS ALWAYS A STATE OF TRANSITION.
A LOT OF PEOPLE TRY TO BRIDGE THE GAP, HAVING CONVERSATIONS
WITH WHITE CO-WORKERS, THINGS LIKE THAT, THEY ALWAYS TRY TO
FIND A CONNECTIVE TISSUE WITH US.
I WOULD BE BONDING WITH SOMEONE.
>> Stephen: YOU AND I.
DOESN'T GET ANY WHITER.
>> YOU AND I WERE TALKING.
I THOUGHT WE HAD A MOMENT, AND ALL OF A SUDDEN, YOU WERE LIKE,
AND GIRL!
YOU PUT ON A BLACK ACCENT -- >> Stephen: LET ME ASK YOU A
QUESTION -- GIRL!
>> PLEASE DO NOT DO THAT.
DON'T START SENTENCES WITH, HEY, DO BLACK PEOPLE.
DON'T DO THAT.
>> Reporter: BECAUSE THEY DON'T?
>> I DON'T KNOW.
I DON'T KNOW WHAT OTHER BLACK PEOPLE TO.
I DON'T.
>> Stephen: YOU CAN ASK ME ABOUT WHITE PEOPLE IF YOU WANT.
>> DO WHITE PEOPLE -- >> Stephen: NOPE.
HMM MMM.
( LAUGHTER ) YOU'VE GONE FROM YOUTUBE TO AN
HOBB SHOW.
NOW THAT IT'S A LITTLE BIT OF A HIRING PROFILE BEING ON HOBB.
THEY MARKET YOU, YOU KNOW, THEY WANT YOU NOT TO BE ABLE TO WALK
DOWN THE STREET.
THEY WANT YOU TO BE FAMOUS.
HAS THAT BEEN DIFFERENT FOR YOU GOING OUT THERE BEING SEEN AND
RECOGNIZED EVERYWHERE YOU GO?
>> IT JUST FEELS LIKE I'M POPULAR IN HIGH SCHOOL, IF
ANYTHING.
IT'S NOT REALLY, LIKE I'M NOT REALLY WELL KNOWN.
>> Stephen: AFTER TONIGHT, YOU WILL BE EXTREMELY WELL KNOWN.
>> THANK YOU.
>> Stephen: IT'S OVER.
( APPLAUSE ) IF YOU HAVE ANY VICES, GET THEM
DONE BETWEEN NOW AND THE TIME THE SHOW BROADCASTS.
>> GOOD TO KNOW.
>> Stephen: YEAH.
HELPING MY FRIEND RETURN SOMETHING THAT BLOOMINGDALE'S
AND I WAS STAND BIG THE CASHIER, BEING BORED.
AND THE CASHIER WAS, LIKE, WAIT, WAIT!
I KNOW YOU!
I LOVE YOU SO MUCH!
I LOVE YOUR MUSIC!
I WAS, LIKE, WHO DO YOU THINK I AM?
AND SHE THOUGHT I WAS A BEAUTIFUL RAPPER AND I SAID, NO,
THANK YOU FOR THE COMPLIMENT, SHE'S BEAUTIFUL.
TWO MINUTES LATER, THIS PERSON COMES UP TO ME AND SAYS, YO!
I LOVE YOU SO MUCH!
AND THE CASHIER DIDN'T HEAR THE BEGINNING PART.
SHE SAID, I LOVE YOU SO MUCH, I LOVE YOUR SHOW, CAN I TAKE A
PICTURE WITH YOU?
AND THE CASHIER SAW ME TAKING THE PICTURE AND SAID, PITCH, DID
YOU LIE TO ME?
I SAID, NO, I'M A DIFFERENT PERSON.
I'M SORRY.
( LAUGHTER ) >> Stephen: I GET A LOT OF, I
LOVE YOU, STEVE CARELL.
I'M, LIKE, I'M NOT HIM.
I WISH I WAS.
NOW, THIS IS BASED ON YOUR OWN LIFE, THIS SERIES?
>> IT'S PARTIALLY BASED OFF OF EXPERIENCES AND A LOT OF MY
FRIENDS.
I HONESTLY JUST WANTED TO CREATE SOMETHING I FELT LIKE WAS
RELATABLE AND WAS SOMETHING KIND OF FOR US BANED US.
>> Stephen: WE HAVE A CLIP HERE.
CAN YOU TELL ME WHAT'S HAPPENING IN THIS ONE?
>> SO WE OPENED THE SEASON WITH MY CHARACTER WHO IS ALSO KNOWN
ISSA.
GOING AND ADVENTURING INTO THE DATING WORLD AND FEELING LIKE IT
GETS A BIT REDUNDANT AFTER A WHILE.
>> Stephen: OKAY.
JIM?
>> WHERE ARE YOU FROM?
HONESTLY, DOESN'T MATTER WHAT I SAY BECAUSE THIS ISN'T GOING
ANYWHERE.
>> YEAH.
I'M INTO BURRITOS NOW.
>> HIGH SCHOOL KIDS?
SOUNDS TOUGH.
YOU LIKE WORKING WITH KIDS?
>> HOW'S IT WORKING WITH KIDS.
TO BE HONEST, (BLEEP).
BUT I'M TRASHED, TOO, SO.
>> SO HOW LONG HAVE YOU BEEN UNHINGED?
>> HOW LONG YOU BEEN ON BOOM?
ARE YOU STILL SINGLE?
( APPLAUSE ) >> Stephen: I UNDERSTAND THAT
A MUSIC CONSULTANT OR SUPERVISOR ON YOUR SHOW IS S SOLANGE KNOWLE
>> YES, FOR THE FIRST SEASON.
INCREDIBLE.
>> Stephen: ANY WAY YOU CAN GET ME INVITED TO A PARTY WITH
BEYONCE?
>> I CAN'T EVEN GET INTO A PARTY WITH BEYONCE.
I ALWAYS JUST MISS HER AND IT JUST HAS BEEN DRIVING ME CRAZY.
I WOULD LOVE TO MEET HER.
IT'S CRAZY, EVEN TALKING TO SOLANGE ABOUT, WHEN SHE WAS AN
EMPLOYEE ON THE SHOW, HEARING HER HAVE CASUAL CONVERSATIONS,
YEAH, ME AND MY SISTER -- AND I ZONE OUT IMMEDIATELY BECAUSE
SHE'S TALKING ABOUT BEYONCE, BEYONCE IS HER SISTER!
SO IT GOT VERY CHALLENGING.
>> Stephen: BECAUSE I'LL HOLD THE BABIES OR ANYTHING LIKE THAT
IF SHE NEEDS THE BREAK.
>> HONESTLY, IF YOU'RE BABY SITTING, I'M BABY SITTING, TOO.
>> Stephen: IT'S A DEAL.
SEASON TWO OF "INSECURE" BEGINS THIS SUNDAY ON HBO.
ISSA RAE, EVERYBODY!