-Our next guests are Emmy- nominated writers, creators,
and stars of shows such as "Sherman's Showcase"
and "South Side," which is now in its third season.
New episodes stream Thursdays on HBO Max.
Let's take a look.
-I'm so happy you guys are here.
This is perfect timing. It's perfect.
Waylon and I were just discussing the urgent need
for more Black-owned businesses right here on the South Side.
-Mm-hmm. This ain't the South Side.
-And this ain't a Black-owned business unless, you know,
he ain't just light-skinned, is he?
-No, no, no. That is a white man. Yes.
-What is this? 1 South Michigan?
So technically this is the South Side.
-No. -I mean, you call it that,
and I'm behind that.
-No. It's not a thing. I'm not behind it.
-22nd is usually what people think is South Side.
-I believe they call this the Wild Ones?
-We're kind of downtowny-ish.
-Mm-hmm. -But it's cool.
-Please welcome back to the show
Bashir Salahuddin and Diallo Riddle, everyone!
[ Cheers and applause ]
♪♪
Welcome back, gentlemen! I'm so happy to have you here.
I'm so happy "South Side" is back.
-Yeah, yeah! -This is a show
filmed in your hometown. -South Side of Chicago.
Let's go, Chi-Town! -There we go.
[ Cheers and applause ] -Thank you, cousin.
-Bashir, I am well aware that you have a very large cast,
a lot of speaking parts in the show.
-Yes. -A lot of friends and family
probably want a piece of this apple --
want a bite of the apple. -Yeah.
You know, it's nice when I'm on set and I look around, I go,
"I'm related to that guy. I'm married to this woman.
This dude owes me money." You know, it's nice.
-So now you're getting him paid. -Yeah. Yeah, yeah.
It takes care of itself. -And I will say, you know,
knowing it takes place in Chicago,
knowing how many of these are local hires
and how many are non-professional hires,
people are deeply funny.
I don't feel like you have any cast members
who don't know how to deliver a line.
-We always say you could count on one hand the number of people
we actually fly in to be on the show.
-True, true.
-Like, everybody in Chicago has at some point --
It's becoming like the Chicago version of "Law & Order."
Like, every actor gets a chance to be on the show.
-We walk down the street and go,
"Have you been on the show yet?" -"'Cause you're kind of funny.
You're funny-ish."
Sometimes when we're filming out on location,
people will come up and be like,
"Hey, man, this is a good scene, but you know what it's missing?
It's missing me!" You know, like...
"Alright, Uncle." -Alright.
-You -- I read -- Diallo, I've read you say
that you want to make this
like Springfield is to "The Simpsons,"
like that big a world.
-Well, listen. Bashir and I met in college,
and one of the things we bonded over
was our love of "The Simpsons." -Hm.
-And, you know, we called it "South Side"
and not any particular character name because we really wanted
the community of the South Side of Chicago
to be sort of the star of the show.
-That's right. We have folks
from all over Chicago who are in the show.
In fact, last month, I was at my mom's house.
You know, like a lot of adults, I was craving a sno-cone.
-Yeah.
[ Laughter ] -Right?
-As one does. -As adults do. Grown-ups.
And then I was like, "I want a sno-cone."
She's like, "Oh, there's a dude on 80th and Vincennes
that sells sno-cones. They're so good."
I went out. The guy was so funny.
He's in the trailer for season three.
We just put him on the show. Yeah, I don't even know
if he knows that we were making a TV show.
He just was being funny, and then the cameras came in.
But I'm so happy he did it. He was so good.
-Yeah. You got a new fan of the show...
-Yeah. -...this year, Bashir.
So, Bashir, you were in "Top Gun: Maverick" this year.
-Yeah. I was. -Congratulations.
[ Cheers and applause ]
-Yeah. You guys saw that? A little indie film.
-A little indie film. The same viewership as --
-Probably, yeah. Same folks.
-But Tom Cruise -- How does it happen
that you get Tom Cruise to watch "South Side"?
-He shot a lot of movies in Chicago.
"Color of Money" is the one I can think of now.
We were talking about it,
and I was telling him that I had a TV show set in Chicago.
He's like, "Let me see it."
So we sent it to him, and I remember one day
I was in the office and I was screwing around,
probably on some websites that I shouldn't have been on.
WorldStarHipHop. Sorry.
I was like, "Nobody with my degree
should be on this website," but I was on it.
And then I got a phone call, and I was like, "What is -- "
And somebody called me.
They said, "Hey, Bashir, I love the show."
And I was like, "Tom!"
But he called me, and it was so much fun,
and I had the great privilege of walking into the writer room,
being, "Hey, guys. Somebody wants to talk to you.
And it's Tom Cruise." -Wow.
-And, by the way, they didn't believe it at first.
They were like, "That's Tom Cruise on the line? Alright.
Get Indiana Jones to phone in."
[ Laughter ]
-"Yeah, Bashir's finally lost it. It only took..."
-Were you in the room when the call came in from Tom Cruise?
-No, I was actually in the room next door,
but I noticed right away, like,
there was a weird sort of, like, crackling speaker phone...
I was like, "What is Bashir doing over there?"
And I go over, and I listen for a couple minutes.
I'm like, "Ah, this is that day
when Tom Cruise calls the writer room."
-You guys want to talk to Maverick. That's right.
-You guys, one of the centers of the show --
And I should say it's all walks of life.
You have cops.
You have people who are in trouble with the cops.
-Yeah. -And you have the center of it
is this store called Rent-T-Own. "Rentione." Excuse me.
-Unclear how to pronounce that.
It's got hyphens in weird places.
Is it Rent Town? -Two T's back-to-back.
It's one of those things. We just didn't give a damn.
We just said, "Spell it the worst way possible."
-And, now, why did you want to make
this sort of business the center of this world?
-Well, this is a terrible business.
-Yeah. -It's a predatory --
No, really. If you guys know --
I don't want to call any names, Rent-A-Center,
but let's just say...
[ Laughter ] Some people know it.
If you're in urban America, you know,
sometimes you go to somebody's house
and they have TV and the couch, and everything is rented.
And then if they don't pay for that stuff,
somebody comes in and snatches it all back from them.
And we thought, what a terrible business,
but what a great TV show idea.
-Maybe we can mine this for some comedy.
-There's something funny here.
-One of the twins on the show, Quincy...
-Shout-out, Quincy. -...who plays the manager.
He used to work at a Rent-A-Center,
and he used to regale Bashir
with these stories about replevins.
It's their form of repossession.
And we did think that, like, out of this tragic sadness,
there might be some --
there might be some solid comedy gold.
-Yeah. -Yeah.
-It is -- I should note one of the things
that I like about the show is no one who works there
thinks it's a nice place to work, either.
-We definitely don't sell the idea
that it's a good business. -Yeah.
-This is a terrible, terrible place
that you don't want to be a part of.
But the funny thing is, is, like,
our folks were a part of it,
and we think that's something people can relate to.
A lot of folks out there have, you know, jobs
they don't look forward to going to.
How do you muddle through those days and still find humor?
And I think that is what makes our show work,
is that there's people who have kind of tough circumstances,
but yet they still find great ways to laugh.
-It is a very deeply funny show.
You shot at the real Lollapalooza in Chicago.
-Yes. Shout-out Lollapalooza.
-And, now, how is that when you're shooting
at an ongoing, active music festival?
-There were a lot of people trying to jump
in front of the cameras. -Yeah.
-Okay. -There was a lot of that.
You know, but we had such a great time.
And, like, shout-out to Lollapalooza
for letting us film at their festival
because they didn't have to say yes to us.
You know what I mean? Like, they --
They allowed us to use all their production values.
And we had rapper Cordae. Shout-out to Cordae.
-Shout-out Cordae. -On the main stage.
So we got to go up on the main stage and shoot up there.
And there were robots. I don't know if that's a spoiler.
I don't want to do a spoiler-y interview.
I don't want to do back-to-back spoiler-y interviews.
-We've already spoiled "White Lotus."
-Here come all the "South Side" season-three spoilers
that you've been avoiding! [ Laughter ]
-That you weren't even aware you were avoiding.
-You guys do not just have the one show.
I also want to give a shout-out to "Sherman's Showcase."
-Let's go. -Thank you.
[ Cheers and applause ]
-This is another
really beautiful piece of world-building.
This is sort of a fictional show inspired by "Soul Train"...
-Yes. -...and inspired by so many
different musical acts of a certain era.
-Listen, we always said that if a show like "30 Rock"
took place at "SNL," our show takes place at "Soul Train."
And we always thought that, like --
You know, 'cause we came up working at "Fallon."
We were always like -- how do we take these songs
that aren't really "Fallon" or NBC-appropriate --
where do we give them a home?
And the home ended up being "Sherman's Showcase."
-That's right. We can do all the music
that NBC was like, "I don't think so."
[ Laughter ]
-"Drop It Low for Jesus"? Not today.
-I don't think so.
-And you're now three -- You have three actual albums
that have come out of your television show.
-Yes. Quality albums out on Mad Decent, but, you know --
-I was going to say. We always loved The Lonely Island.
We love those guys. -Yeah.
-And we love that their music --
I remember when -- you know, Diallo was a deejay.
We used to live in New York. He would be deejaying parties.
He would put on things like --
-I remember I put on "Lazy Sunday."
-And it killed. -The party kept going.
-Yes. -And we were always like --
And today, by the way, turtlenecks and chains.
So I don't know what I was thinking.
-You guys can't see the audience,
but everybody's in turtlenecks.
-Yes. Turn the camera that way.
-We cannot afford an audience camera,
but I assure you that's right.
[ Laughter ]
-But we wanted to make songs that you could appreciate
whether you're listening to them at home or in the club,
and that means a lot. Like, this season,
we have songs that sound like Parliament-Funkadelic.
-Yes. -We've got a song that's, like,
contemporary trap, hip-hop, but it's by a rapping dinosaur.
-There you go. -You know, it's not Barney.
Nothing's changed. -No.
He's got a gold chain with a block on it.
-He's got dreads like Future. It's pretty choice.
-Yeah. -It's pretty choice.
-Well, very few people have any shows as good as one of yours.
It's incredibly impressive to me that you have two of them
currently available for us to see,
and it's just so wonderful to see you guys as always.
-Thank you for having us. -Thank you very much.
-You guys, that's Bashir and Diallo.
New episodes of "South Side" are available
Thursdays on HBO Max. We'll be right back
with more "Late Night."