- This is the first time we've done this
and I don't know how hard people are gonna go.
- I knew that, if I played
mind games, it would throw him off.
- [Annie] I feel like I'm gonna have
nightmares about this challenge.
- [Shane] If Money Race was a professional sport,
hall-of-famer right here, baby.
- Hello.
I've recently come into a bit of money.
(suspenseful music)
Beautiful, aren't they?
The mind reels what could be purchased with such a bounty,
and that's why I've enlisted
the help of three of my coworkers
to help me determine, once and for all,
what's the worst way I could spend my riches?
Let the games begin!
(grandiose orchestral music)
Welcome to The Great Money Race.
I'd like to hear what's the worst thing
you guys have ever bought, starting here with Aria.
- I wanted to see, you know, if money can actually
buy friendship and happiness, so I actually
did spend $100 on a Craigslist ad
for someone to be my friend for a day.
It didn't really work out.
We hung out one day, never saw each other again.
- [Garrett] That is a terrible way to spend $100.
- Absolutely.
- Annie, what's the worst thing you've ever bought?
- Off the top of my head, probably a Zune.
(Shane chuckles)
- Shane, what's the worst thing you've ever bought?
- Someone on my dormitory floor my
freshman year of college sold me a mouse,
and I kept it for about 48 hours before I realized
it really stunk up the very small dorm room.
And then I took it up to the fourth floor
and left it there and just put
a note on it that said "I need a home."
- Free mouse.
- I think I paid $40 for it.
- $40 for a secondhand mouse.
How much do you think a fresh mouse costs?
- Four bucks.
(laughter)
Well they feed those things
to snakes left and right, so yeah.
- You all have given me great confidence that
at the end of this, I'll know the worst way to spend $100.
I'm going to give you each $100
and your goal is, yes--
- Yeah, I see 'em.
- My eyes are down here.
- Okay.
- [Garrett] Your job is to spend the $100
that I give you as poorly as you can.
You have two hours to come as close
to spending the total $100 as possible
in no fewer than four stores.
Every item you buy has to be daisy-chained to the next item,
so the last letter has to begin the next thing you buy.
For instance, if you went to the store
and bought an egg, you'd have to go
to another store to buy a GameCube.
The winner will be determined entirely by me.
- What's at stake?
- Nothing less than my best $100 bill.
It's gonna break my heart to part with her,
but if you can spend $100 as poorly
as I know you can, it'll all have been worth it.
- And after this, you'll be back to zero?
You'll have zero dollars?
- Don't worry about my finances.
- Okay, I am, a little.
(laughter)
- I think it's time we get you guys your money.
- Okay, whoa! - Oh whoa!
- Gentlemen.
(glass smashing)
- Thanks.
(glass smashing)
- Go!
Let The Great Money Race begin!
What have I done?
(pensive music)
- Starting The Great Money Race now.
- So I'm just gonna head out to some sort
of mall to make it easier on myself
and hopefully some stupid (bleep) is there.
- [Aria] Where's your car, Shane?
Where's your car?
- Aria already giving me some sass.
I'm getting away from him so he can't look at me.
- There's a movie theater here, maybe I should
just buy a ticket to a really (bleep) movie.
- I'm paying my parking ticket.
So the thing I buy will have to start with a T,
which is perfect 'cause I need a tie.
- Start big, give myself a lot of options,
and then narrow it down from there.
It's Money Race, this is The Great Money Race.
- Right now I'm paralyzed by choice
and can't pick a first item.
- [Shane] There's a fishing pole here.
Don't know why no one would need that.
- [Annie] I don't know what this is, but--
- [Shane] I think we found our winner.
- [Aria] No dollar store ties for this guy anymore.
- [Annie] Oh, hell yeah.
- I got $87 to go, let's do it.
It's Money Race.
- I want people to know that
I'm a rich man that wears silk ties.
Hello, everyone!
I paid $35.90 for this!
- I feel like I'm winning.
I don't know how the other people are doing,
but I feel like I'm winning.
- Vinyl ends with L.
Oh God.
Maybe I should consider this log pillow.
- I got a nutcracker, so that ends on R.
Time to get radishes.
- Next thing I have to buy starts with an E.
- If I'm gonna win this thing,
I gotta start thinking bigger numbers.
- I'm definitely losing.
- Oh, there's a Hooters!
'- I got an idea, I don't know if
this is a good idea, something I maybe regret.
- I have like $4 left, I'm out of breath, I'm very sweaty.
- Wow, the pleasures that money can buy.
- Miscalculated, thought I had $4, I have like $14 left.
- 'Cause this is Money Race.
(pensive music)
- [Garrett] Welcome back!
I hope you found the experience freeing.
Shane, you were the first to return.
You should present first.
- So I started out by going to a sort of big box store
and the first thing sand to me was patriotic nutcracker.
He's wearing camo, and it's not just even
the regular camo, it's that weird digital camo
that they wore in Desert Storm.
- What a terrible purchase.
- [Shane] Yeah!
From there, I went down to a local grocery store.
So we're working with R,
and there were plenty of good treats in there,
but I wanted to spend this money poorly.
- Radishes.
- [Shane] Yes.
- Oh, and those are fine looking radishes.
- They look beautiful. - Oh no, they are dripping!
- They're dripping, these babies are dripping.
(whistle)
(loud crunch)
- And how's she taste? - They're fresh as hell.
They don't taste, I mean--
(loud crunching)
Problem was they were $1.49.
You know, I gotta hit that hundo.
I walked down to the local thrift store
because I thought, you know, if I want
to spend a lot of money in Los Angeles,
where do I have to go?
The thrift store.
Hat, $39.42.
- Wow, that is way too expensive for that hat.
- [Shane] From there, this big ol' huggable guy.
(Garrett gasps)
$29.99, but it was 50% off,
which still allowed me to have a little fun.
And keep in mind, this is maybe 25 minutes total.
(snaps)
I'm darting while this idiot
over here is driving around in his car.
"Ooh, stuck in traffic."
- Alright, alright, piece of (bleep).
- There weren't a lot of other stores around there.
There was a Super Cuts.
So what I did is I got a real bad haircut.
(laughter)
And that's just a classic bowl cut.
The woman, she didn't want to give me the haircut
but I told her it was for a play.
So that's putting me up at about $96.
About three bucks remaining, I went to a local restaurant,
a big fast food chain, not a lot on the menu with a T,
but then I saw the words "triple cheeseburger".
(laughter)
And baby, that put me at $99.62.
- Well, that is a tremendous waste of money, Shane.
- I had a blast.
I don't know if I won, because this is the first time
we've done this and I don't know
how hard people are gonna go.
Was this a little stunt-like?
Yeah, but it was a bad way to spend money, so.
- Annie, you were the next person to return.
- So the thing that caught me up was
that there were too many choices.
- The monied man's burden.
- I got a Call Me By Your Name vinyl,
a very stupid purchase.
- [Aria] Is that the one where he
fiddles himself with a peach?
- He does, yes.
- But anyway, this vinyl was $41.99.
- Whoa!
- Why wouldn't you want...
- Hold on!
- Strong out of the gates!
- Do you have any sort of streaming music subscription?
- I do, and I also don't have a vinyl player.
- That is a very stupid purchase.
- [Shane] What a waste!
- And so, vinyl ends with an L.
The smallest lipstick.
- Let's see, it's red, indeed, lipstick.
So that gives you a K.
- The K leads to it's a mint tin that says Kurt.
- And do you know anybody named Kurt?
- I don't think I do.
- What a tremendously bad purchase.
- Does anyone know any Kurts?
- I know a Curt with a C.
- Oh, he doesn't count.
- Kurt candy, and then the Y led to yogurt
that we could get for free at work.
- Oh, paid money for something that
you could've come back here and gotten for free.
Terrific waste of money!
- The T leads to a truck.
- [Garrett] A truck!
- [Shane] Oh!
This is a bad looking truck, I gotta be honest.
- It is a pretty boring looking truck.
- So that leads to a kitchen knife set
that's probably not very sharp.
- Knife.
- Which led to...
- That's an E.
- An E vitamin.
- Do you have a vitamin E deficiency?
- No.
- [Garrett] Do you know what vitamin E helps with?
- I, no.
- I've never even heard of it.
- I don't think I've ever heard of vitamin E either.
- I certainly have not.
(crunch)
- [Shane] Well you're getting...
- Still munching them radishes.
- [Shane] In that radish over there.
- He has one in each hand.
- Are you gonna eat the tails?
- Would you judge me if I did, Shane?
- Alright, guys!
- [Shane] Alright, okay.
- Let's keep it all on the racetrack.
- [Shane] Yeah!
- My grand total was $96.99.
- $96.99, so not quite as close as Shane came,
but still tremendous, really a lot of big wastes of money.
- Do I think I won?
I'm not confident, but you know, maybe I'll be surprised.
- Aria.
- Yes.
- You were the last to arrive.
What did you purchase?
- I really wanted to look at American consumerism,
specifically as an allegory to the Red Scare in the 1950s.
- What the (bleep) are you talking about?
Get outta here.
- He gave you your time, Shane.
- Excuse me, yes please, I need some silence.
- Okay, I'm sorry.
- He gave you your time. Alright.
- But yes, let me begin.
So the first purchase was a parking ticket.
- [Garrett] Uh huh.
- [Aria] I went to Hollywood Boulevard and, of course,
the criminals there, the extortionists,
they don't offer free parking,
so I had to pay $2 for parking.
- No validation?
- There was validation involved.
And with the T, I purchased this
very luxurious 100% silk tie.
- Wow, can I?
- Yes, absolutely you may.
(pleasing music)
- That's, it's incredible.
- So a tie, that leaves you with an E.
- Of course, one of the most beautiful
childhood icons right now, Elsa of Frozen lore, yes.
- Well, it's a movie, Frozen movie.
Have you seen the movie?
- I've seen parts of it.
- Oh, he's only heard tales of it 'round the campfire.
- Ah, but she's beautiful.
- Alright, very good, so you have almost
no understanding of the Frozen universe
and you bought yourself - Absolutely not.
- A useless action figure from it.
- Elsa, yeah.
- Of Frozen, yeah.
- Elsa with an A, exactly, A.
So I bought a treat that I thought
we could all enjoy together, which were these Airheads.
- Airheads.
- I've never had one before.
- Sort of like a taffy.
- Oh, I did not know there were multiple flavors either.
Oh, look at that.
- Do you know anything about...
- Aria, you... (laughter)
- Airheads, S, and so I went into
a truly American establishment,
which is of course Hooters for a shirt.
As Americans, we should be supporting
local, local American companies.
- Where's that T-shirt made?
(upbeat guitar music)
- That's irrelevant.
- So, shirt.
- Shirt, and then finally, - So that's a T.
- I was there already.
- Yeah?
- But I thought the T, T... (laughter)
- T is indeed a letter.
- Why're you looking at me like I'm crazy?
- You have gone to four different establishments.
So are you saying you doubled up at Hooters here?
- I may, yes, I doubled up on Hooters.
- What have you done? - I really
wanted to support them.
- Now, Aria, may I ask, was there a woman
who checked you out at Hooters
and did you just sort of keep wanting
to impress her by...?
- She, she's really...
- What was her name?
- Melissa.
(laughter)
- Alright.
- Had that one ready to go.
- And she really sold me on this.
And some may view this as unnecessary,
this tote, T for tote.
Girls just wanna have sun, first, very funny.
- It is funny.
- Yeah, girls just wanna have fun.
- You think that's funny?
- I laughed.
- Okay.
- [Aria] So this is it, and what's great about this,
and you know is that we can put all this in one tote bag.
Look how much this carries!
- I'm struck by the fact that this journey
seems to have made you lose your mind.
I've never seen you quite like this.
- You know, sometimes you get into
very deep conversations with people you meet,
and Melissa, she's a very thoughtful person.
You guys wouldn't understand, you haven't met her.
- Add it all together
what'd you have? - In total,
I believe came to a nice tidy sum of $96.49.
- $96.49, that puts you in the 96th percentile.
- Win or lose, I think I've come out of this
with beautiful memories as well as some purchases
that I really think will last me a lifetime,
especially this tie, 100% silk.
(pensive music)
- This has been tremendous wastes of money
no matter how you go about looking at it.
Aria, like I said, it seems like
you really lost your mind going out
there trying to buy these things.
Annie, you bought products that you'll never be able to use.
A dump truck for a child that doesn't exist,
a Call Me By Your Name vinyl
that you have no way of playing.
And Shane, you are going to have
to spend more money to rectify
the spending of the money that you have.
- Or I don't.
- Because Shane came closest and was fastest
and cut his hair to look like that,
Shane, congratulations, you are
the inaugural winner of The Great Money Race.
- I love it.
- This is my best $100 bill and it's yours now.
- Wow, thank you, thank you.
- Very well done. - Thank you.
- [Garrett] Really, a tremendous waste of money.
- You know, clearly Shane won, so.
It's fine.
- Shane wanted it most of all, he deserves that hundo.
- Well, well, well, looks like it pays
to be good at Money Race, because I won money
and I raced for it, and now it's mine.
And I just feel like the belle of the ball.
Pays to get a bowl cut.
That's actually not true, it doesn't ever pay
to get a bowl cut, but today it does.
- Let us know in the comments how you would spend $100
and don't forget to daisy-chain your answers.
(triumphant music)