- Okay. (Issa drinks)
(crew laughs)
All right, this is the worst day of life.
Hey, I'm Issa Rae and I'm taking cheap shots with Cosmo.
(lively music)
All right, there will be three rounds
with five questions each,
and for every question there's a drink.
One of those drinks is a cheap shot.
Bottom shelf liquor baby,
the kind of smells like nail polish remover but I'm game.
Nail polish remover is really tasty.
Have you ever drank acetone?
(crew laughs)
I either have to answer honestly or risk death.
Just kidding a hangover, which I just had last night.
So we're in good company.
Let's do it.
In round one, I'll be taking shots at myself.
The drinks here are hard seltzers,
four our regular and one's spiked with a shot
from a $13 bottle of vodka.
All right, personal shots.
"Barack Obama said he loves your work.
Beyonce told you you were beautiful.
Which compliment meant more and why?"
Very easy, Beyonce is saying, I'm beautiful.
I'm sorry, thank you, Mr. President.
He said he loved the soundtrack at the time,
that was a collaborative effort.
Beyonce was looking at my face
and she hugged me and touched me, and it was all about me.
And Beyonce is kind of my president.
"You once said I would do my 20s even dumber if I could."
Be dumb in your twenties, I did say that.
"What's the dumbest thing you did in your twenties?"
Oh my God, that's...
They're infinite things but the dumbest?
Oh, I lied to this guy about being from Atlanta
(Issa laughs)
to not see him again, to not talk to him
so I put on this accent.
(Issa laughs)
It was so bad.
Then he ended up seeing me
walking out of Kaiser with my mom, clearly living in LA
and he was just like, "You effing liar."
And my mom witnessed all of that
and I had no coverage for it but just generally lying.
- [Producer] Can you show us the accent?
- I was basically like...
(Issa laughs)
I did it in the in the chu.
So I'd be like, what's up with chu?
What's up with chu shorty?
And he was like, "What?"
I don't feel comfortable saying a whole sentence.
(crew laughs)
"Usher recently serenaded you at his Las Vegas show.
Who is your hall pass?"
I don't have a hall pass
and I'm wondering if it's too late to ask for one.
I think it is.
Does that mean I have to take a shot or is it...
- [Producer] I think so.
- I have to take a shot because I don't have a hall pass.
Okay, hard seltzer.
(Issa spits)
Okay, that's not...
It should just taste like water.
The bubbles burn.
"Name a role you didn't get but think you deserved."
That's hard because like as an auditioner,
I'm a bad auditioner, but I know...
Oh, you know what?
I'm gonna take this shot.
(Issa tongue spitting)
That's so bad.
"What is one red carpet fashion look you regret wearing?
Tell us why and who designed it."
I have it off the top of my head.
My glam team is in the room and I will shade them all.
It was like top down a miss.
I went to the ESPYS,
it was like an upside down trash bag dress,
the hair was not right.
I just looked like I was at the wrong place.
And you know sometimes people write a article about you
and they'll use a random picture
and sometimes they choose that
and I'm like, "Why would you...
There's so much and you chose this."
So yeah, I hate it.
That's round one.
Round two is 30 second shots.
I'll have 30 seconds to answer trivia questions
about my career or take a shot.
I have to get these right about myself?
These drinks are whiskey ginger ales, four are top shelf
and one is mixed with cheap whiskey from a plastic bottle.
Mm, I love plastic bottles.
"IMDB lists you as a writer on five different projects.
What are those projects?"
I don't (censored) know.
I...
"Insecure", "Rap Shit"...
What do I do? (clock ticking)
I be writing.
"Awkward Black Girl" (clock ticking)
This is crazy, I do write.
Five projects?
I haven't done that much yet.
What am I missing? (buzzer ringing)
Damn, I gotta take a shot?
- [Producer] "The Choir" and "Black Twitter Screening".
- That's (censored) up, those are...
Okay, IMDB, now that you expanded to internet shit,
it could be anything.
(Issa scoffs)
(Issa groans)
That...
That didn't even have ginger ale in it,
that was just whiskey.
My eyes are watering.
(everyone laughs)
"You were nominated for four People's Choice Awards in 2020.
What were the categories?"
What?
I...
Four People's Choice Awards, it had to be I guess best show?
(buzzer rings)
But I don't know what the other categories are.
Best actress? (buzzer ringing)
Four categories, me?
What other things?
Best person. (buzzer ringing)
Best...
Because it's best people, Best People.
(buzzer ringing)
Best outfit. (buzzer ringing)
- [Producer] Female Movie Star, Comedy Movie Star,
Drama Movie Star, Comedy TV Star.
- I was killing it in 2020, okay.
(crew laughs)
All right, this is the worst day of life.
"You were born on January 12th,
name three other celebrities who share the same birthday."
I just talked to a girl about this last night
but I was drinking.
Jeff Bezos. (chime rings)
Shonda Rhimes is the day after.
Somebody, this a white lady.
It's not Bette Midler.
Is it Barbara Streisand? (buzzer ringing)
No, you can't tell me?
Three other celebrities.
Damn, I was about to...
My best friend.
Michelle Obama? (buzzer ringing)
No, I wish.
- [Producer] Howard Stern.
- Oh, I knew him.
That's who I met by the white lady, actually.
I got that wrong. (everyone laughs)
Yes.
- [Producer] Amerie.
- We're birthday twins?
All right, this is for Amerie.
"Name the four other women you appeared alongside
in Essence Magazine's Game Changer issue in 2015."
Something I know,
Mara Brock Akil, Ava DuVernay, Debbie Allen, Shonda Rhimes.
Woo, that was one of the best days of my life.
"Name five magazines you graced the cover of."
"Elle", "Vanity Fair"... (chime rings)
No, yeah, "Vanity Fair", (chime rings)
"Marie Claire", (chime rings)
"Variety", and... (chime rings)
Oh Jesus...
- [Producer] Where are you?
- Where am I right now?
- [Crew Member] "Cosmo".
- "Cosmo"! (everyone laughs)
Thank you, woo!
Round two, complete.
Round three, the category is cheap shots
and I'll be taking literal cheap shots at everyone.
The drinks are French 75's,
four are made with my Prosecco, Viarae.
In the meantime, the cheap drink is mixed from a bottle
of $6 Prosecco and $12 gin.
$12 gin, sounds terrible.
"You've always described yourself as awkward.
Name one celebrity you've worked with
who you think is even more awkward than you and why?"
I mean, I think there's no controversy
in saying Michael Cera and Kate McKinnon,
I'll throw 'em all under the bus.
They're endearingly awkward but Kate,
just know that if you see her, she doesn't wanna be there.
And it's relatable so yeah, that's it.
(Issa laughs)
"You hosted SNL in 2020, name a skit you were in
that you didn't think was funny and why?"
I mean, there is a skit that I pulled myself out of
that I was just like, "Ah, this is not my humor."
That still aired, they still did it.
They were like, "Cool, we'll still do it."
But you'll have to watch that episode.
It was just a little too fly overstate humor to me,
and I'll leave it at that.
"Rank these actors from most
to least dateable in real life."
(Issa gasps)
Kendrick Sampson, Y'lan Noel, Jay Ellis.
Now I could go to route and be like, "Jay, he is married."
so he's technically the least dateable.
The second least dateable is for sure
Kendrick Samson because outta his mouth,
he does not like to date.
He's not a player but he's just a lot.
And then Y'lan, I think he's probably most dateable,
but even he's like, just don't date actors.
All actors are trash, honestly.
All handsome men, beautiful gowns but not dateable.
Oh, "You've had many guest stars on 'Rap Shit',
Who was the most difficult to work with?"
We had a lot of guest stars this season.
Damn...
Yeah, everybody was very pleasant.
We work with a lot of music artists.
I mean, you can take a guess.
(glass taps)
All right, (Issa spits)
if this is my Prosecco, it's delicious.
(everyone laughing)
That was a cheap shot? - [Producer] That was.
- All right.
"Rank these celebrity alcohol brands from best to worst.
Skinny Girl by Bethany Frankel,
Aviation Gin by Ryan Reynolds.
818 Tequila by Kendall Jenner, Ciroc by Diddy."
I've actually tried all of these, except for one
that would be 818 Tequila by Kendall Jenner.
Sorry girl, no offense but hate it.
Skinny Girl, I used to be obsessed with in my 20s.
I thought I found this secret
and then I had it a couple years ago and it is trash.
It is poison but I respect her hustle.
Diddy doesn't have Ciroc anymore,
so by that I'll rank it lower.
And then I gotta give it up for Aviation Gin,
it actually, it's great and I love the marketing behind it.
Ryan Reynolds is kind of a legend,
so that to me would be the best.
Thank you guys so much for watching me play Cheap Shots.
Make sure to check out and taste the Viarae Prosecco,
it is not a cheap shot.
(everyone laughs) (upbeat music)