-So, you made a documentary about white privilege.
-I did. My own, specifically. -Your own specific
white privilege. And this is was an idea you had
post-2016 election. -Postmortem, I — Yes.
And in 2016, I don’t know if you guys know,
there was an election. -[ Chuckles ] Yeah.
-A pretty big one. I didn’t like the way that went.
-Yeah. -So, I had a hard time with it. And, you know,
before the election, like, my biggest decision was
whether I was gonna build a slide that came out
of my bedroom balcony for adults that went straight into my pool. That was, like,
my biggest stressor. And then, the day
after the election, I was running around
my neighborhood passing out water bottles
to Mexican workers like, “We love you.
You’re here. You belong here.” They’re like, “We’re legally
here, so back off, bitch.” [ Laughter ]
So it was a confusing time. -Yes.
-And I was very upset, and I dug deep, and I went
to therapy for the first time. -Yeah.
-The first real time in my life at the tender age of 42,
I think. And I got real
about my entitlement, about being spoiled, about what it’s like
to look outside of yourself, get your head out
of your own ass, you know? And I started to look around
and realized just how bad, like, of bad shape we were in
and how little I knew about it. So I got educated. -And with white privilege,
this was something that, is it safe to say you were
a little just oblivious to before you had
this sort of introspection? -Yeah. Like, I thought,
“Oh, I’m super talented, and I work really hard.
That’s why I’m successful.” It’s like “Whoa, whoa, whoa,
whoa, whoa.” When you start to read books,
it’s like a person of color wouldn’t have
had the career I’ve had, wouldn’t have gotten away
with the things I got away with, and I had no
accountability for that. So for me, it was a deep dive
into just understanding what it’s like to be a person
of color in this country, as good of an understanding
as I can have, because, obviously,
I can’t understand. But I wanted to do something that wasn’t about
me collecting a paycheck. It was about communicating
and just contributing something, you know, in a more
thoughtful way. So I started with
my own ridiculous privilege and lifestyle,
which is, you know, absurd. So I learned a lot, and we have to really
pay attention to people that are unlike us. -And I think, you know, I feel
similar probably to you, which is, you know, you,
as a white person, you succeed, and it felt very hard, you know, when you are in it
and your perspective. And you just need to realize,
like, “Oh, I’m not saying white privilege doesn’t mean
it was easy for you. It just means
it can be so much harder for people that don’t have
that first step in the door.” -Absolutely. It means that when
I get pulled over by the cops, I don’t have to worry about it
being a life-or-death situation. -Which is a huge difference. -Exactly, so —
-You mentioned — One of things you talk about
is shoplifting, how that is something you did which then becomes
a slap on the wrist as opposed to what it could be
for someone else. -Yeah, I mean, my ex-boyfriend’s
in the documentary. He’s a black man named Tyshawn
I dated when I was 16. And I know everybody knows
that I’ve dated 50 cent, and my friend said, “Oh, great. Now people are gonna think
you only like black guys and you discriminate
against your own race.” So I would like to say that
I’m available to white men, too. -That’s very nice of you to say.
-Okay? I want it clear that I don’t
discriminate against white men. -That is very sweet of you.
[ Laughter ] -Even though, you know,
you guys know what you did. [ Laughter ] Um, but — Wait, what was
the question? Sorry. -Shoplifting.
-Oh, shoplifting. Well, he and I got caught,
“A,” with three dime bags when we were 16, he was 18. Every time, they let me go,
and every time, he got arrested. And he ended up spending
14 years in jail. And I never thought about that
at the time. My director of this documentary made me go back there
and revisit that. I was like, “No more
ex-boyfriends.” Like, “I’ve met up with a
couple, and it doesn’t go well.” So I wasn’t that into it. But it was important. And, you know,
there are examples. I mean, I’ve walked
into an airport. You know how annoying
an airport can be, and the slowness
of a transaction with the person
behind the counter or at a Hudson Bookseller. I mean, I’ve definitely
walked in, looked at her and looked at the slowness
of the transaction of what it was going to take,
taken a book, and just waved $20 up at the — up at the camera —
the security camera and be like, “Yeah, I’m taking
this, and I’m leaving. I can’t deal
with the slowness of this.” And when I was talking
to her about that, I go, “Is that white privilege?” She’s like, “No, white people
aren’t even doing that.” -Yeah.
[ Laughter ] -She was like,
“You just have problems.” [ Laughter ]
So it was — -Yeah, don’t pin that
on our race. -Right.
[ Laughter ] -That is very specifically
a Chelsea thing. -I was like, “Yeah, it turns out it is very specifically
a Chelsea thing.” A lot of my issues are very, you know, centered
around my own experience. -You were — You were arrested
when you were 21. What was that for?
-I got a DUI, but my sister,
who’s in my dressing room, my mother had given me her I.D., like, as one mother does —
as a mother does, so that I could drink
earlier than I was, you know, legally able to.
-Sure. Good parenting. Yeah. -My mom was just like,
“Whatever you need to get the hell
out of this house.” Like, “If you need a fake I.D.,
take it.” Anyway, I got pulled over,
and I forgot that I was 21 at that point,
’cause it had only been a week, and I gave them my sister’s I.D. And apparently, my sister had
reported me to, like, the FBI or something, so I had to — -For stealing your I.D.? -She — She was Mormon
at the time. So, she was really just, like,
out to get me — -Yeah, they call the FBI
left and right. -You know how Mormons are.
[ Laughter ] -They got it on speed dial.
Yeah. -It’s like they’re in bed
with the FBI, basically. No, so, I ended up
spending like 48 hours in this — in L.A. County
women’s prison. And then I had to go to this
class where you had to get up and tell your DUI —
You had go to DUI school, which is basically a school
you go to for like 8 to 10 weeks where they teach you
how to get out of your next DUI. -Okay.
-They’re basically like, “Don’t ever admit –” I’m like,
“What kind of class is this?” But when I got up to finally tell my story
about my experience — -Were you nervous
about telling your story? -Yeah, I had diarrhea.
Like, I had diarrhea — Every time I went to that class,
the fear of getting called on, I had diarrhea.
-Yeah. Oh, wow. -Public speaking was the
scariest thing you could imagine and I was like,
“There’s no way I can do this. I can’t talk publicly.” But when I did get up,
I couldn’t get back down. I couldn’t stop talking, ’cause
the audience was like with me, and they were listening to me.
And my story was ridiculous. I called the cop a racist.
He was white. I mean, none of it made sense. And when I got off, somebody’s like,
“You should do stand-up comedy,” and I was like, “Yeah,
that actually makes sense — me talking and no one
being able to interrupt.” So, that’s kind of
how I got into stand-up. -So, I guess what you’re saying that any young potential
stand-ups out there is get that first DUI.
Get in front of people. -That’s right.
[ Laughter ] -You know, work it out
in front of an audience. -Yeah, and if you could
steal someone’s I.D., go for that, too. Why not? -Congratulations
on the documentary. It’s always so great to see you.
-Thank you. -Give it up for Chelsea Handler,