Troubled Duos: 8 pairings that just can’t make it work | ChicagoLIVE Prime-Time

Fox - 32 Chicago
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1 Video View·Nov 3, 2026
Where do they come up with some of this stuff?
Okay, so troubled duos.
Again, duos that were together and had some trouble.
There was issue.
Let's begin here.
With the one that started it all, what do you say?
What do we got on our little card over here?
Okay, this is the one.
Trouble Duo.
Well, so we got eight of these, okay?
So here's number eight.
This is the inspiration for all of this.
25 years together, these two gentlemen here, okay?
Super Bowls, Monday Night Football.
Now, apparently, things are getting awkward.
There's been F-bombs dropped.
There's been awkward cold iciness.
There's probably some poor producer
at ESPN somewhere before every kickoff
standing between them like a parent on a road trip.
Okay, you two, nobody's got to talk.
Let's just get through this together.
Four quarters, and everyone goes their own way.
Capisce?
That is our troubled duo number one.
And hang on, wait a minute.
Bears score alert.
Okay, what do we have?
Bears just got a field goal.
Bears are up 10-3 now.
Bears are up 10-3.
There is your Chicago Bears score alert.
If anything else happens.
I'll let you know.
Back now to our troubled duos.
So we go from number eight to number seven here.
And this one, oh yeah.
Hall & Oates, legendary musicians here.
Hit after hit, decades together.
But eventually, lawyers.
They went from, you make my dreams come true,
to you'll be hearing from my attorney.
And honestly, you know a partnership is really going bad
when even the greatest hits album kind
of starts to sound a little bit like evidence.
Now, if you don't know the backstory, if you're a music nut at all,
dig into this because, again, these guys had some great songs,
but behind the scenes, they could not stand each other,
and it got ugly, it got messy, personally,
financially, and business-oriented.
as well. Trouble duo number six tonight.
Now listen, if you grew up watching Saturday morning
cartoons, you know that this duo just never really worked out.
It's the duo of the Wile E. Coyote and
the Acme products. For decades, Wile E. Coyote,
he bought everything from this company, from rockets
to explosives to catapults, giant magnets,
spring-loaded shoes, even jet-powered roller skates.
And in that time, not a single one of those things worked,
but Wiley was dedicated to
the company, and he kept buying and buying.
At some point, though, Wiley, this is on you.
You don't need another rocket.
You need something like Consumer Reports.
Just one review, that's all it would have taken.
Can you imagine?
Acme Rocket Skates, one star.
Great acceleration, brakes arrived.
A little bit too late.
That's our troubled duo number six.
Now, here's one for all the fast foodies out there.
Troubled duo number five.
We've been there a couple times, right?
These two have known each other for years.
There's still no chemistry here.
The machine is standing right there.
It has lights.
It has buttons.
A little screen.
Looks like it's healthy, but you pull up
to the drive-thru line and you ask,
Can I get a McFlurry?
No.
Why?
Shake machine broke.
Why is the machine always down?
And there's nobody there to repair the thing, it seems.
And everybody acts like this is just normal.
They say it with the same confidence as we're out of napkins.
At this point, the machine isn't really broken.
It's just got boundaries against everybody,
including you, at 10-something at night,
when all you want is a chocolatey, vanilla-y, M&M-coated McFlurry.
Or just an ice cream cone. You can't get one.
I digress.
Let's move on.
Here is number four's troubled duo.
We're sticking with a food theme,
but we bring this back more around to Chicago.
These two, there's no future here.
You can be careful all you want.
You can lean forward.
You can wrap that sandwich in foil.
You can use napkins.
You can order it dry.
It does not matter.
Somehow, someway,
a drop of gravy from six feet away will find your white T-shirt.
Italian beef can smell confidence.
The worst part is when you get that stain on your shirt,
You never notice it until a couple of hours later
when you're looking in the mirror and
you've already spoken to about six different people.
And there's that stain from lunch staring you down in the face.
It's not really lunch.
It's character development.
So that's a troubled duo, the white shirt and the Italian beef.
Now, again, sticking with the Chicago theme,
our number three troubled duo.
Well.
Let's discuss this for a minute because technically these two have met.
I mean, every car.
Has one of these, the turn signal.
It's right there next to the steering column.
It's very convenient.
Yet, for some Chicago drivers, it feels like revealing
classified information if you want to try to use one.
Where am I going?
Well, that's between me and the Lord.
You see somebody, they drift across three lanes
of traffic, no signal, no warning,
and then suddenly, after they're already there, the signal comes on.
Thank you.
So very helpful.
Helpful.
It's not a turn signal anymore.
A press release at that point.
You've already done the action.
Signal, then make your move across six lanes of traffic.
Maybe that's just me once again.
We're down to the final two here, and these get better, I'm told.
Number two's most troubled duo, Chicagoans,
and the phrase, it's only 20 minutes away.
This relationship is built entirely upon lies.
20 minutes wins Sunday morning.
At 2.30 a.m. during a mandatory citywide evacuation?
Yeah, then maybe you can get somewhere via car in 20 minutes.
It never works that way.
You put this thing in the maps, it says 48 minutes and rising.
20 minutes in Chicago is not a measurement of time.
It's fool's optimism, and it never works.
All right, our last one tonight.
Our last number one trouble duo.
This one is Chicago drivers and the speed limit.
Damn it.
Oh.
Most of our highways, the sign says, what, 55?
55.
If you're going 55, you are not driving.
You are scenery on a Chicago highway system, right?
Let's be honest here.
65?
People are still passing you.
70, people are passing you.
75, someone behind you is furious.
Let's say you're going 85.
You might be going 85, but somehow, someway,
a Nissan Altima will appear out of nowhere,
six inches off your bumper,
flashing its lights like you are ruining its day.
When you're going 85, then they will pass you doing 92.
Usually with one headlight, a temporary spare,
and half the bumper ripped off.
Because that's why.
The sign says 55, but Chicago drivers treat
this more like a suggested donation, not the actual law.
And if you really want to think about this,
the relationship between Chicago drivers and the speed limit
is probably the healthiest one on this list,
because at least everybody knows that this relationship
Isn't working.
So there you go.
Those are just some of our troubled duos.
We'll see you in a couple of weeks.
