-Are you enjoying your summer? Are you having fun?
-I'm having a great summer, actually.
-You are? -Yeah.
-Did you do a yacht party yet?
-The yacht party is actually this weekend.
-Oh, really? -Yeah.
We're doing -- I do a yacht party every year.
That came about because I tweeted one day --
I was like, "Oh, I just want to do yacht ish with my friends.
I want to be able to call them and be like,
'Y'all wanna yacht?'"
And then, one year --
-That's just something -- Just a random thing you want.
-So, I wanted to use yacht as a verb.
-Yeah, "You guys want to yacht today?"
-"Y'all wanna yacht or what?"
And then, one day I was like, "Oh, I could do this."
And then did it, and it's been the most fun thing ever.
-But, like, what do you do on the yacht?
-You just -- You drink. You dance.
You have a very good time.
And it's just like, you know, friends and the best people.
But this year, I did a little too much.
It was the third year doing it, and I over-invited,
'cause I'm just like, "Oh, you do that,
because people are going to drop out."
-Yeah, of course. -That's inevitable.
But a lot of people aren't dropping out,
so I don't know if we can -- I want to, like, force people to
be like, "Hey, you sure you want to come?
Because -- It's not a problem, but nobody's --
-Not one person. Everyone said yes?
-Yeah, everybody's saying yes,
which is a great problem to have, I guess,
but I just don't want that.
-All right, let me know how it works out.
-Thank you.
-You've already had a great summer,
'cause you just received an award.
This is the Emerging Entrepreneur Award.
-Yeah.
-And you had -- You got very good buzz on your speech,
by the way, which was very funny.
-Thank you so much.
-How did you come up with your idea for this?
-I always, like -- It's always nerve-racking
trying to figure out what you're going to say at these things,
and I was in the hair-and-makeup chair that same day.
And I was just like, "What am I going to write?"
And I was going to do the typical, like,
I was grateful to get the award.
-You're honored. Yeah. -I was honored.
But I was like, "Mm, 'F' that."
Like, I want to be --
I want to be, like, not humble about it."
And I started thinking about some of my
favorite hip-hop artists,
who don't know what that means at all.
They don't know what humility is.
And I was like, "That's how I need to move
and that's how I need to operate."
So I wrote that speech with that inspiration in mind.
-I want to take a look at a little bit of the speech.
Here's Issa accepting the Emerging Entrepreneur Award.
-Emerging Entrepreneur Award. Duh, bitches.
I'm closing all doors behind me, so if you didn't make it in...
oops, your bad.
Figure it out.
Entrepreneur means, "I did that [bleep] by myself."
And to everybody who claims to have helped me get here...
okay, and?
In conclusion, entrepreneur till I die.
I deserve this, bye.
[ Cheers and applause ] ♪♪
-I loved it 'cause it is so not you.
-It's definitely not me.
I was really, really nervous about doing it,
but they took it really well.
-Yeah.
And you're back writing more "Insecure," right?
-I am.
We're in the writers' room right now.
It's super, super exciting.
-You've just blown up since the first time we had you on.
I mean, you're doing movies and everything.
So, I mean -- And I'm happy that you're still doing "Insecure."
-Of course.
I mean, that's, like, my bread and butter.
Well, I mean, I love doing it, too,
but it's my bread and butter.
But, yeah, we're entering our fourth season.
-We're -- [ Cheers and applause ]
Thank you.
I got really excited, because we usually do
eight episodes every season,
and Prentice and I, the show runner,
decided that we were going to do 10 this year.
And, so, we knew that like four months ago,
and I was super-excited to tell the public, our viewers.
And, so, just recently announced it,
and the response was like, "Um, we didn't ask for that.
We asked for 20 episodes or an hour."
Like, they were mad ungrateful.
-"We gave you two more shows." -I mean, like, thank you.
We gave you two more episodes,
but our viewers are just really rude, so...
-We want 30 episodes. -We want 30 episodes.
It's never enough.
-Let's talk about your other show now.
This is "A Black Lady Sketch Show."
-"A Black Lady Sketch Show." -Congrats on this.
This is fantastic. -Thank you.
-It's HBO. -Yes, created by Robin Thede.
-Oh, I love Robin Thede. -She's phenomenal.
And, you know, she -- This is her brainchild.
-How'd you get involved with Robin?
-Robin and I go really back.
I was thinking about it, and I used to work with
Larry Wilmore for "Insecure."
And during that time, it was just like the two of us,
you know, working on this show together.
And then he got the opportunity for "The Nightly Show."
And as he was developing that, simultaneously,
he used to always talk about Robin and be like,
"Man, this girl is just -- She's phenomenal, man.
She's just killin' it. She's so smart."
And I started to get jealous, like,
"Oh, who's this smart bitch that he keeps talkin' about?",
when we clearly had a bond.
And, so, then, when the show got picked up,
he brought me on to audition as a correspondent.
And I was mad nervous.
And it turns out I was auditioning in front of her.
And I bombed that audition, but she was so gracious.
She laughed at every joke, even though it wasn't funny.
She just made me feel great.
And didn't get the correspondent role,
but I was just -- I appreciated that about her.
And then, for "Insecure," we brought her in to audition
for the role of Tiffany,
but we ended up choosing Amanda Seales,
but still kept in touch.
And, so, when I heard her show "The Rundown" got cancelled,
I love that show, love her, and could not wait.
And I was like, "Girl, this is it.
We got to work together. What you got?"
And she brought "A Black Lady Sketch Show."
-Oh, that's fantastic. [ Cheers and applause ]
I want to show everybody a clip of "A Black Lady Sketch Show,"
which premieres Friday at 11:00 p.m. on HBO.
Take a look.
-Every morning, I wake up one hour early
to put on my Fenty highlighter before my man wakes up.
I'm exhausted,
but I can't let bae see me with my bare face, you know?
-I've never been bare-faced in front of a man.
I'm afraid all the athletes I date wouldn't know
what to do with a woman who takes her cheekbones
off every night.
-Consider this. Hmm?
Do they even appreciate that you
put them on in the first place?
Moreover, is a partner who doesn't appreciate
the cheek work deserving of the cheek twerk?
-Never thought about that. -That's good.
-I mean, how cool... [ Cheers and applause ]
-Come on. -Angela Bassett?
-Angela Bassett! -Angela Bassett?
-Angela Bassett.
-I mean, is there other cameos in --
-Oh, my God. There's so many cameos.
First of all, bow down to Angela Bassett.
You know, in a sketch called "Bad Bitch Support Group,"
you can't not have her as a leader.
And I feel like that's why it was so easy to get her.
She was like, "Of course I'm a bad bitch.
Of course I'm-a do it."
But we do have so many amazing cameos,
you know, like Patti LaBelle, Laverne Cox, Aja Naomi King.
So many amazing guests that who just down to be a part of this.
-I love that.
Congrats on this thing, another cool new thing
that you're doing.
I love you. Issa Rae, everybody.