- I thought my situation was bad.
My mom owes me $150.
(laughing)
- That's it?
- I want my money, mom.
♪ I was born on the South Side ♪
♪ I was raised on the South Side ♪
♪ Everybody sit together like we in the lab ♪
♪ Cause it ain't no side like the South Side ♪
- Welcome back to Cooler by The Lake.
- Yeah!
- Yeah.
Where we discuss all things South Side
and ask the important questions like,
where the fuck is that nigga Dave Hollister?
- We miss you, Dave.
- Loved you... for like one album.
I'm your host, Will Miles.
- And I'm your host, Langston Kerman.
- And of course we have our guests today,
the esteemed actress/ comedian, Marilee Williams.
- Yeah. (clapping)
- And the esteemed rapper/ designer, Vic Mensa.
- All right.
(laughing) (clapping)
- I mean goddamn, I can't believe I didn't think of that.
That's a nice little hustle.
- [Langston] So, on tonight's episode of South Side you saw
Simon and K really just try to drum up a new hustle
with their popcorn business.
- I got kids. I know 20 different ways to make popcorn.
- Oh shit, this place is haunted.
- The question that we are asking
what are some of the best hustles that you guys know
out of Chicago, out of everywhere...
- Got it.
- Yeah. - Yes. (chuckling)
- I think one of the best hustles
that has come out of Chicago in recent times
is Jussie Smollett, man.
- Oh. - Jussie Smollett's
hustle with the Nigerians.
(laughing)
Nigerians are top rate for messes.
Like I bet the Nigerians approached him at a party
- I could see that. (chuckling)
- And they came like, hey - Brother...
- I can do some things for you.
(laughing) - Brother.
- Give me $300.
- People do not appreciate you, what you got going.
- You going to be okay, yeah. - These people don't
appreciate what you bring.
- Hey, that was one of the best finesses of all time.
- No, I'ma be honest, - I mean, also not,
- poorly executed. - It was the worst finesse
of all time. - Poorly executed
but the thought. - But also just like most
just gutsy,
you know what I mean? - Yeah, yeah,
It was gutsy, I'll give you that.
- Even the police got there he still had the rope.
- Racist attacked you some (mumbles).
- Some Chicago shit.
- Some real Chicago shit.
- This is a good segue way.
Have you all ever been scammed by a hustler?
Have you ever been the victim of somebody else's hustle?
- Yes, I've dated a man from Chicago.
(laughs)
If that's what you're asking.
- Exactly! Hell yeah, what the fuck.
- Hey, he's agreeing (laughs).
- I've been scammed a million - Aye, we aint shit
what's up? - Time.
I'ma tell you all about the consummate scam.
So, one of my good friends
I'ma leave him unnamed in this.
When he was locked-up I was the only nigga
that came to visit him.
When he got out he came on tour with me.
He was staying with me in Beverly Hills,
another one of our friends that wasn't as much my friend but
he was just kind of staying too sending his little packs
back to Chicago and shit. - Yeah, yeah, yeah.
- Somewhere along the line he got my credit card and
actually cracked my card while living with me.
He was buying chains from my jeweler,
he shopped out with me,
he paid me rent money from my money,
putting homies up in hotel suites all night
till he ran up about 15 racks.
And this is how deep the hustle was.
When I found out that I had been defrauded
his name didn't flag anything cause
I bought so much shit for him.
- Yeah.
- So, the other nigga that was staying with us,
my homie find the way to finesse and blame the other nigga
and make it look like he's the one that cracked my card.
And that nigga had just got locked-up so he like,
in my ear, he like,
oh yeah, we got to kill this (laughs).
(laughs)
- For, his style's very Chicago.
- Aye, you know me.
I'm like,
you know what I mean
I'm turnt up at this point as I'm going like
we got to kill him?
(laughs)
Yeah, we got to kill this (laughs) for sure
now that you've mentioned it.
(laughs)
And I think I'ma do it myself.
- I heard about this dude who lived in Snoop Dogg's house
for like three months.
Just cause he went to a party over there once
and then just stayed
- And Snoop Dogg didn't know? - Snoop Dogg didn't...
He didn't know he was there.
- That's so sick.
- So, he was just like hiding out like, okay they gone?
I'ma take a shower.
(laughs)
- What?
- That's amazing!
- It's the best hustle I've ever heard of and that's...
- That's not a hustle that is illegal!
- One time a motherfucker in Chicago
climbed
in the roof
of the building
next to my crib
came across the roof and into my house from the
like fire escape or some shit
and this nigga just pop-up in my motherfucker hallway like,
(clap hands) can I rap for you G?
(laughs) - I'm like, Geez (mumbles).
- That is drunk!
- Like he's so lucky I didn't come out
with my shit right now.
I would've just blew your brains out.
Just cause you wanted to spit a 16.
- He did a Batman move just to give you his mixtape?
- That shit was decent as hell.
I, see, I wasn't,
I didn't listen to him rap then and there.
I was like get the fuck out my house.
But by the time we got outside I was like,
I'm too forgiving,
you know what I mean? - Yeah.
- I was like Fuck it, spit that shit.
- He was getting his escorted out rapping.
Okay, listen, fake (laughs)
- Is he famous now?
- No!
(laughs)
You don't get on doing shit like that you get shot!
- I swear I thought he was about to be like
and that boy is Little Nas X.
(laughs)
- He sang Old Town Road for me that day.
(laughs)
- And I slept on him (laughs).
- I told him,
as the police was taking him away...
- I slept on him. - And was saying,
I was saying,
now you going to need a white man on this song
if it's going to be a hit.
- You are good boy.
- A Billy Ray.
- He might add something like that.
- Let me call up Billy.
- Anyway, this has been another episode
of Cooler by the Lake.
One more time for our guests
(hand claps)
Vic Mensa and Marilee.
- I'm your host Langston Kerman.
- And I'm Will Miles.
Thank you for tuning in
we adore you.
- Protect your neck.
♪ I was born on the South Side ♪
♪ I was raised on the South Side ♪
♪ Everybody sit together like we in the lab ♪
♪ Cause it aint no side like the South Side ♪