Undercover Boss - S08E09 - Darius Rucker - 卧底老板
Jul 30, 2026
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Video Summary
AI GeneratedGrammy-winning artist Darius Rucker goes undercover as \"Jackie Middleton,\" a retired teacher, in Austin, Texas, to discover raw musical talent. By hiding his celebrity status through prosthetics and a disguised voice, he connects with aspiring artists to provide mentorship, financial support, and industry connections without the bias of his fame.
Tonight on Celebrity Undercover Boss
Hey man, can I get a little more vocal?
Darius Rucker, Grammy Award winning recording artist
Nobody's seen me with that much hair in years
Goes undercover in search of America's next great musical act
He'll travel to Austin, Texas to scour their legendary music scene
I'm your stagehand for the night
We're running an open mic
In hopes of finding new up and coming musicians to work with
In his search for undiscovered talent
My name is Jackie Milton
He will have to conceal his musical ability
I'm just going to sing as bad as I possibly can
Jackie's voice is a little bit rough around the edges
And what will happen when lives are forever changed
This is the biggest blessing ever sent to our daughter
It's crazy great, it's amazing
Is this really happening right now?
This is real
Find out next
On Celebrity Undercover Boss
World famous recording artist Darius Rucker is a platinum selling superstar
Who has sold more than 30 million albums
Skyrocketing to success with one of the most iconic bands of the 90's
Hootie and the Blowfish
Darius has won multiple awards and had 6 top 40 singles
But this music maven came from humble beginnings
My name is Darius Carlos Rucker
And I'm a musician
I was born in 1966 in Charleston, South Carolina
And raised by my mom
Single mom most of the time
My mom was a nurse
Working hard and trying to get by everyday
There was always music in my house
My mom sang, she was amazing
And it was all about the music for us always
Growing up I was listening to everything
It didn't really matter to me
When I met the Hootie guys in college
At the University of South Carolina
R.E.M. was that one connection we all had
Even though we all had different musical tastes
And we just started playing
We struggled the whole time
For almost 9 years we were just out on the road
Trying to build it up
We put out a little CD that we sold
Just out of the back of our van
In that mom and pop record stores
And the story goes that David Letterman
Was driving home one night
And Z-100 played Hold My Hand
For the first time they'd ever played it
And Letterman heard it
Called his booking agent and said
I just heard this band are doing a Blowfish
I want them on my show
Ladies and gentlemen Hootie and the Blowfish
Then that Friday we played Letterman
And everything changed
It was crazy
We were selling out all the arenas
And we won two Grammys
And five American Music Awards or something
And four World Music Awards
And there was a moment
We were the biggest band in the world
And then one day one of the guys in the band goes
I just don't want to be a touring band anymore
I want to tour every summer
And so I just remember him saying that
And me thinking
Alright I'm going to try to do this country thing
Since arriving on the country scene
Darius Rucker has released four records
Had seven number one country singles
And has been inducted into the Grand Ole Opry
In 2009 he won the CMA Best New Artist Award
Becoming the first African American
To be given the honor
Alright here we go Darius
If I told you
All the stupid things
I've done
I blame
Don't be any young
But I was old enough to know
I know
I was a country music fan growing up
So I would say to everybody that would listen
Man I'm going to make a country record someday
Good one
One of the happiest days of my life
Was when I realized none of my kids want to be musicians
Because the music business is hard
It's hard to get in
Once you get in it's hard to stay in
For every person like me
There's 500,000 people that never make it
Hello
Hi
How are you?
Darius good to see you
This is the first step of the prosthetic makeup process
Okay
So we're going to get a copy of your face
And then the prosthetics will be sculpted on top of that in clay
And then run in silicone
Just make sure they don't know who I am
I'll figure out how to change my voice
That's the thing I'm thinking about the most
Let's get the face done first
I've been lucky enough to have 30 successful years playing music
But if it wasn't for a few people that helped me out along the way
I'd probably still be playing at small bars and fraternity parties
So I'd love to find some up and coming talent
That I can mentor and help launch their careers
Oh
Oh yeah
I'm going undercover because I don't want anyone to treat me differently
Just because I'm Darius Rucker
If they think I'm just an average Joe
They'll probably be a lot more honest
And I'll be able to see their true talent
That was crazy
So this is going to come back to the lab with us
And we're going to make a custom silicone prosthetic
Nice
Come on in
Hope you're ready
So just like you asked, we made you some prosthetics
Oh nice
This is your forehead prosthetic
Nice
We really, really love this wig
Oh, don't you see me with that much hair in years
Decades
Let's do it
Awesome, let's go
Alright, when you're done
I'm going undercover as Jackie Middleton
A retired school teacher who dreams of one day playing music for real
The people that I'm going to be working with
They will think that Jackie is competing for the chance to launch a career in the music business
They'll have no idea that I'm actually Darius Rucker
Alright, let me see
Let's see what we got
Alright
Here's Jackie
Oh my goodness
Cool, I like it, I love it
Tonight, I'm going to go to the Speakeasy
I hear the Speakeasy's got the best open mic in town
Harry Connick Jr., Quinn Stevonnie, Nora Jones
A whole bunch of big names have played here
Tonight, I hope I get really lucky and find somebody who really moves me
The girl that's running the open mic tonight, she thinks
I'm Jackie Middleton from South Carolina in this music competition show
How's it going, man?
I've been in a band since I was 19
So I never got around to doing the open mic night thing
And I'm hoping to God they don't ask me to try and sing a song
Jocelyn
How's it going?
I'm good, thank you for allowing me to do this
I love the jacket
The jacket's so great
Jackie wasn't exactly who I was expecting to see
An older guy wearing, you know, a jacket that has a little bit of tang to it
This is so cool
Thank you
Right on
If he wants to wear it, why not, you know?
All right, so tonight we're running an open mic
I'm responsible for getting everybody signed up
And I usually end the night with me performing
So I also want you to also end the night
All right
Oh man, Jocelyn wants me to get up and sing a song
And the one dead giveaway would be my voice
You'll go right before me? Does that sound good?
All right
It's a little nerve-wracking but, you know, I'll try to change my voice a little
And see what happens
Yeah, I guess time will tell, you know
We'll know in a little while if we pull it off
So what we're gonna do next is
I'm gonna have you find three different people
All right
Ask them what time slot that they want
Where they're from
Any musical influences
You know, really, just really try to interact with them
Like how we're interacting right now
You know, we're becoming wonderful friends
You're my best friend now
Absolutely
Jackie and Jocelyn, you know?
Do your thing, man
And get back to me when you're done with three people
All right
How y'all doing?
What's your name?
I'm Corey
Nice to meet you, Corey
What's your name?
Danica
Nice to meet you
What time do you want to play today?
We'll go 10-25
10-25?
What time do you want to play today?
Right after him
It's nice to meet you guys
Nice to meet you
We've seen you up there
Yeah
Jackie is a little bit stiff
So what time do you want to play tonight, Dina?
You could tell that he was a little bit awkward
But we can work on it
Nice to meet you, too
All right
I got three
Here, let's come sit back down
All right
Do you think you got, you know, solid...
No, absolutely
Do you think you've done a solid job on this?
Absolutely
Do you know any musical influences that they have?
No, uh, no
All right, okay
All right
He does need to work on connecting a little bit more
Because you're able to bring that to the stage
And be able to sing to them and know their life
And I think that's very important
What about even, like, getting to know them as an individual?
Like, why not become their friend?
There's nothing else to do in this life, you know?
Oh, I agree with that
So what we got to do is we got to fill up the rest of this list
All right
All right, perfect
Hello
You got a big piano in your hand
Here, you know what we could do?
Head bop
Love it
Jackson was so upbeat and so positive
And when I was, you know, trying to learn how to run
Phil and Mike Knight, she was so helpful
And wanted me to succeed
I think I missed a couple people that walked in
There's a guy up there
She wanted eye contact and she wanted physical contact
And for me, I love that
I mean, I'm Southern
That's what we're born and raised to do, you know
Everybody, welcome to the Speakeasy Open Mic
My name is Jocelyn, I'm your host tonight
So our first person that we got coming up tonight, his name is Dino
Leave your gear
With your satisfaction
Open Mic Night is always full of surprises
Because you never really know what you're going to get
And it started out pretty good
The thing I love the most is, like, everybody had respect for each other
And wanted to hear what the other guy did
I thought it was great
And then you got into some moments that weren't so great
Thank you
Hey everybody, we have a wonderful human coming up tonight
His name is Jackie
Now, Jackie has been helping me out with the Open Mic tonight
Some of you may have met him tonight
Right on, yeah, let's get a clap going, please, thank you
Yeah, I was nervous going up there
Because I know I can't really be me
Are you ready for this, Jackie?
I think
One of the hardest things in the world I could do is go up and try to be awful
But I don't want anybody else to know who I am
My name is Jackie Middleton
Are you ready for this, Jackie?
I think
Jocelyn wants me to sing a song, and I know I can't really be me
My name is Jackie Middleton
One of the hardest things in the world I could do is go up and try to be awful
But I don't want anybody else to know who I am
I'm just going to put this retainer in
And I'm going to sing as bad as I possibly can
On a warm summer's day
On a train bound for nowhere
Met up with a gambler
We were both too tired to sleep
So we took turns staring
Out the window at the darkening
When Jackie got up on stage and performed, I didn't really connect with him
For the taste of your whiskey
I'll give you some advice
The tempo was a little bit off, and when it comes to doing open mics
He could work on doing songs in this century
You got to know when to hold
Know when to fold
Jackie's voice is a little bit rough around the edges, but we can get him a vocal teacher
When the dealing's done
Thank y'all
But I probably wouldn't be on the same bill with Jackie
I don't think he's ready right now
Everybody, this was Jackie's first time performing here tonight
All right, everybody, my name is Jocelyn, I'm going to get this going
Okay, this is a song called Nothing Left to Say
I hope you like it, it is an original
Every time I make a mistake
Comes back around some other day
I'm not a fool, I don't understand
Why I repeat myself
And all we need to do
Gotta get a move on, gonna get my groove on
Not about to let this slip away
I'm on the highway, gonna do it my way
And climb this mountain all day
Never gonna give up
When she started singing, I went, you gotta be kidding me
No one's gonna stop me, no one's gonna stop me
She really blew my mind tonight, she blew me away
Her voice, she was really something special
I mean, the world needs to hear that girl
Thank you, everybody
That was awesome
All I gotta say, wow
Thank you
I mean, really, honestly, wow
Thank you
You blew me away
So how do you think that you did tonight?
The performing part was okay
Okay
I've done better
And how old are you again?
I'm 62
62? Good
And I don't want it to be a big thing
I just want to sing for people with us
I don't want it to be a big thing
It's hard to be a big thing at 62
Can I tell you something?
Anything is possible
That's true, I believe that
You have to recognize that, okay?
I could be a lot more confident
You know what I do when I practice my confidence?
What's that?
Jocelyn, you're the best
Can you say that?
Darius, yeah
I let my name slip out
Jocelyn, you're the best
No, no, can you replace that with Jackie?
Jackie, you're the best
And I was like, Darius, I mean, Jocelyn's great
And she was like, no, say your name
Can you say it louder than that?
Jackie, you're the best
But, you know, I don't think she caught it
You know, she didn't see him to catch it
Let's talk about you for a minute
You know, where are you from?
I'm from Omaha, Nebraska, man
So what's your story, you know?
Family, you got family in Nebraska?
I have an older brother, actually
Who, when we were little
It was just me and him and my mom
She was a single parent when we were young
And so she was never home
And it was just my brother and I
We had to make up things
I'd grab a vacuum
And a broom would be my guitar
And I'd, like, put a string around it
So I was 14 years old
I saw Ed Sheeran play on YouTube
I was like, wow, I want to do that
I relate to Jocelyn a lot
My mom worked her butt off as a nurse
Sometimes 60 hours a week
You know, and we wouldn't see her
She was saying her and her brother
Had to have a great imagination
And make things up
That was my life
What's next for you?
I'm a starving artist right now
I'm getting gigs all around
Just basically anything
That will keep me climbing
She's got it
I don't know what it is
But she's got it
It's not a matter of if
It's a matter of when
She's a superstar
Thank you for tonight
I thought you hugged
Oh, of course
I want to work with her, mentor her
And help her take her music
To a whole new level
You are awesome
Right on, man
Right on, Jackie
So we got to pack up our guitars
Oh, these old bones
These old bones
Hey!
What happened with Stubbs?
Oh yeah, we got an inside guy
We're working with right now
He's gonna go carry some cases around
Be kind of one of the road guys
I thought you were a roadie
Yeah, you're a roadie
Roadie for a day
Nice, it's been a long time
Since I've done that
Tonight I'm going to Stubbs
Stubbs has been around since the 70s
Everybody's playing here
From Muddy Waters to Johnny Cash
My manager made a call
And got me a job here tonight
As a roadie
I'm going to be working
With Treble Soul
Who's apparently a new
Up-and-coming duo
Who play all around Austin
Hey, what's up?
How you doing, man?
Jackie
Hey, Jackie
Nice to meet you, man
You helping out
With the bands tonight?
Absolutely, man
I'm excited
They think that I'm
A retired school teacher
Competing for a chance
To launch a music career
I'm going to go in there
I'm going to do my job
I'm going to listen to the band
And you know
I'm hoping they blow me away
Hi, I'm Hannah
What's your name?
Hannah
Nice to meet you, Jackie
I'm Kurt Jones
Nice to meet you, buddy
Kurt Jones?
Yeah
Jackie, nice to meet you
You ready to help us?
I'm ready to load some stuff
Let's go, buddy
Let's do it
Where you guys from?
I'm from Rockdale
He's from West Monroe, Louisiana
We just got engaged
And we have a baby
And she's two years old
Nice
Named her Presley
I'm an Elvis fan
How did something with music do?
She's got some lungs
I don't know
Let me tell you
The song's called White Water
Just lay it wherever you can
All right
I'm going to grab
An extra set of strings
Okay
I think that's about it
All right
Are you sure?
I got the door
You guys have a place
Have you played Stubbs before?
The one
Going towards
Luke and Bach
How long have you guys
Been playing together?
Three years
What about you?
Me?
Yeah
I'm a teacher
Really?
Yeah
I'm just out here
Doing this game show
So what is it you guys
Need me to do for y'all?
All right
We would like you
To get some stools
All right
And just bring them
Up on stage
And then after the show
I'll help you unload
Awesome
Can't wait to hear y'all play
Thank you
Don't run upstairs
And grab those stools
Appreciate it man
All right
My name is Curt Jones
This is Hannah Prestridge
We're called Treble Soul
We're going to be with you
For a little bit
I'm going home
Gonna load my shotgun
Way by the door
And light a cigarette
He wants to fight
Well now he's got one
And he ain't seen me crazy
He's at my face
And he shoot me like a record
Oh that sound
Like a real man
I'm going to show him
What a little girl's made of
Gunpowder and lead
Hannah's voice was
a force of nature
And I was like wow girl,
you go, do your thing
There we go
All righty
Tell them if we do
a little Rizla music
for everybody
Thank you buddy
Oh
All right guys,
we're going to have to tune
Just when you think
these guitars are tuned,
they're out again
All right guys,
this next song right here
is my favorite
We had our daughter,
her name is
Presley Lane Jones
She just turned two
the January 8th
So six months
in the pregnancy
Presley was sitting
on my right side
of my kidney
And so I got the size
of a softball
And they started
giving me hydrocodone
And so I got addicted
to it
And basically,
long story short,
I ruined my entire
family's life
It went from having
to everything
to having nothing
It just turned around,
you know
When people love you,
they really love you
No matter how bad you,
screw up
And here we go
So this is
called Addiction
Because that's
what I had
If you ever need a drag
You can kiss my lips
If you don't hold back
Then we don't have to quit
Baby, if you need a fix
With my affection
Baby, let me be
your addiction
Let me be
your addiction
Your addiction
You go to an end, son
Let me be your heartbeat
That keeps you alive
Your instinct
That helps you survive
from all this hurt
I don't want just one more kiss
On your lips
Addiction
Thank you, thank you, thank you
You guys have a safe trip home
And God bless you
That was awesome
Thank you, buddy
I appreciate it
Their songwriting is so close
What he was saying was great
But it just needed
a couple little tweaks
that would really
take it to the top
And I really was
sitting there going
I'd like to rewrite
that song
Actually, I'd like
to cut that song
That was sweet, man
Thank you, man
That was awesome
Do you play guitar?
I do play guitar
Will
Our string kept going out
Yeah, man
We really, really
appreciate you
Oh, absolutely
Is this how y'all
make a living?
This is all we do
Oh, that's awesome
It gets scary
I mean, that Addiction
song was great
Probably if you saw
the original paper on that
I probably had tears
all over that paper
Really?
I was crying my eyes out
doing that song
But I mean
I was in rehab
Oh, were you?
Yeah
She was a month away
from me
You know, and it's one thing
When, you know,
you have your baby
and you're messing up
all the time
Oh, absolutely
But then your baby
gets taken away from you
Like, you know,
you have to go to this rehab
or else your baby
will be gone forever
I would never want
that to happen, you know?
Absolutely
When you started
playing together
you surprised how
that you could
make a living at it
We've been told
it's possible
but we took that chance
and went toward it
If you're gonna do it
do it all the way
or don't do it at all
Right
And don't give up
The raw talent is there
With his songwriting
and her singing
and his singing
was great, too
They got what they need
to make it
They just need to
learn some things
You're too good to give up
I appreciate it
That means a lot
It really does
Absolutely
Let's take this
stuff outside
Alright
I was about
Curt and Hannah's age
when I started
playing with Hootie
I'd love to help them
as much as I can
Because they can make it
They can make it
Coming up
Jackie meets a talented
young street performer
I will be a success
It's all for you
And later
You ready?
He takes the stage
for one final performance
So rock me, mama
What's happening?
I'm undercover
in Austin, Texas
to find some new
musical talent
Today I'm going out
on 6th Street in Austin
There's street performers
everywhere around here
busking as they call it
A lot of stars
have started as buskers
on the street
just playing the music
Everybody from
B.B. King to Ed Sheeran
Jewel was discovered
that way
It's a great way
to have people
hear you play
and I'm going to go
and see if I can
find some talent
She tied you to
a kitchen chair
She broke your throne
and cut your hair
And from your lips
she drew
the Hallelujah
Hallelujah
The guy that was on
the corner singing
was the only guy that had
people around him listening
This is the first song
I wrote, it's about my mom
I still see your eyes
They're just like mine
And I'll show you
I will be a success
It's all for you
His voice is smooth,
it's what every singer wants
His voice is so effortless
Oh, thank you
Absolutely, man
What's your name?
Demir
What's your name?
Jackie, Jackie Middleton, man
Jackie Middleton,
that's an awesome name
Jackie Middleton
You have a great voice
Thank you, I appreciate it
Yeah, man
How do you get into busking?
You thinking about busking?
I'm thinking about it
What are you thinking about?
I'm thinking about
giving it a shot for a second
We'll have a competition, man
A competition?
I'll go over here
and you stay here
and we'll busk
and whoever makes the most money
the loser buys
the other one a drink
You nervous?
I'm a little scared
I'm a little scared, you know
but scared's okay, I think
Yeah
Scared's okay
I'm keeping an eye on you
All right, I'm done
Don't put it away
Absolutely, man
Do it for you
I'm really looking forward to
like seeing him perform
because it's not easy
being a busker
like singing in the subway
or singing in the street
For all the times
I made you mad
I'm gonna give you
things you never had
Thank you
You know, I started my band
when I was 19
and we were always on the road
We never had any time
to really be busking
so I got out there
and I tried to do my best,
but it's so hard
I know a thing or two
about getting the audience
to listen to me
because I've played
to 75,000 people
but watching people
just walk by you
and not even pay
attention to you,
that was tough.
But the beer, you know,
it was making it
look effortless,
like this man
just killing it.
Did he give me a beer?
Yeah
You know, I made $12.
I still got it.
This is my $12.
I'm gonna go buy me a beer.
Hell, in Austin,
I might get 4 beers
for $12.
Amazing woman
take her life
Make it a game
and then break the dice
Listening to him,
he might have cracked
a few times.
I wonder why
I can't sleep at night
I mean, it wasn't perfect.
I'm not perfect
when I perform,
but if he's persistent
and he continues
doing what he's doing,
he'll be able to
be a musician,
like an actual musician.
Thank you, man.
And you tell me
that's your first time
in the street busking?
Wow.
How'd it feel?
Oh good, you know,
some people stopped
and listened
and that was nice, man.
Yeah.
Let me and you
go sit down somewhere
and have a drink.
Okay.
So how'd all this
start for you?
Like, all the street performing,
the singing with you,
where'd it start?
So I was born in Brooklyn.
My parents broke up.
Then everything
just kind of went downhill.
My father went to jail,
my mom developed schizophrenia,
she was on drugs.
So I spent the 5 years
from 12 to 17
in group homes
in like really
violent environments.
I remember night after night
I would sit in the hallway
and cry
because I missed my mom,
I missed my dad,
and I just kind of felt
like I was in the world
by myself.
Just one day, man,
I was walking to my room
and I looked in the mirror.
I was just asking like,
what am I doing with my life?
Yeah.
And the next day I woke up
and decided to make a change
and that's when I decided
to buy a guitar
because I always wanted to.
So that's kind of how
it all started for me.
If you could wake up one day
and be where you want to be,
what is your dream for all this?
I stopped dreaming
a long time ago, man.
Like, I'm living my dream
right now.
Don't you want to make records
and be out there on tour
and do stuff like that?
I will do it.
But it's not that
I want to do that,
that's just a result of
what I truly want to do
is connect with people.
Demir loves what he does.
He's a musician's musician
not because of the way he plays
but because of the way
he lives it,
the way he loves it.
Some of my best days out
I made the least amount of money.
But I, like, I went home
and I had a new song.
Yeah.
Some old lady started dancing.
Those are the moments
that, like, really, you know,
keep me going, so.
Absolutely.
Who Need a Blowfish
was nine years
before we got a record deal.
And we got lucky.
We played Letterman
and he changed my life.
Demir is a guy
who needs one ring.
I gotta do something
to help him.
As big or as small
as I can do,
I gotta do something.
Good talking to you, man.
Yeah, man, good talking to you.
We should get back out there
and bust some more.
You want to?
No.
I think it's about time
I told everyone
who I really am.
The people I met this week,
they think they're here
to judge Jackie
one last time
for the competition
reality show.
Hey, y'all.
Hey, man.
You ready?
Yeah.
Oh, my bad.
I'm sorry.
Here, you want?
I think he was very nervous.
I mean, who wouldn't
be nervous, right?
Give me a second,
I mean, I'm not really sure
what's happening.
Felt like Jackie
was this old Jackie
and became a new Jackie.
Right now,
I'm still kind of like,
what's happening?
It's like, what is this?
Jackie sounded 100%
like Darius Rucker.
I hear my baby
calling my name
and I know that she's
the only one.
And if I die in Raleigh,
at least I will die
free.
That was fun.
Be honest.
Y'all know who that is, right?
Darius Rucker.
This has been
an amazing journey.
You know,
meeting all these folks, man,
and talking to them
and hearing their stories,
it just reminds me
of how hard people work
to achieve their dreams.
I can't wait to meet them
as Darius Rucker
so I can help them
with their careers.
Hey, y'all.
Oh, my gosh.
How are you?
Good, how are you doing, man?
How you doing?
It's great to see y'all.
Wow.
Wait a second.
You're the country artist
here, aren't you?
I'm Darius Rucker,
the country artist.
I recognize you.
I actually saw you.
You were the first
African-American artist
that I had saw.
Really?
As a country artist, yes.
Wow, absolutely.
Wow.
What do you think
about Jackie singing today?
It sounded identical,
like, for real.
Yeah.
Like, completely.
I'm pretty sure
you guys have figured out
that I'm Jackie.
Mm-hmm.
laughs
Wow, okay.
Curt and Hannah.
So I went undercover
to meet some people
that I could help,
and I met you guys,
and I love you guys.
You're kidding me.
No, I'm serious, man.
It was really great
to watch you guys get up there
and just do your thing.
Hey, y'all.
Thank you.
Hannah, your voice
was incredible.
I mean, you know,
and Curt, you were singing
and you played
with so much passion,
so much passion
that your guitar
went out of tune.
I play guitar,
and this is the guitar
that I play all the time.
You're kidding me.
And I want to give you
this Gibson Hummingbird
because that never
goes out of tune.
And Hannah,
you know, I got you one too.
Thank you.
You know?
Is this for real?
This is for real.
I don't know what
to say right now.
Let's put those away.
Okay.
I guess you can't play music
and have babies.
Oh, God.
You know,
I love what you're doing
on stage,
and I want you
to keep doing it,
so one of the best music
schools in the country
is in Hollywood, California.
It's called
Musicians Institute.
I want to put you guys
through that school.
Mark.
I want to pay
for all your books.
I want to pay for
all your private lessons.
I want to pay
for your apartment.
What?
You know, you can learn
to produce your own records.
You can learn more
about composition,
more about playing,
more about your voice.
I want you to learn
everything you can
about the business,
and, you know,
it's a big move
to California,
so, you know,
I'll give you $20,000
total to help you
with everything
to make sure
you can take care
of everything.
Oh, my God.
You're kidding me.
Oh, my gosh.
I have a question.
Yes.
Why us?
Because y'all are special.
Your story's special.
Well, stop it.
You make me cry.
This doesn't happen
every day.
It won't happen today
for you guys.
This is the biggest blessing
besides our daughter,
I mean, ever.
So I just want to
help you guys
and give you a hug.
Absolutely.
You can have a hug.
Golly.
Absolutely.
Darius Rucker
just changed our lives forever.
You guys are the real deal.
Thank you so much.
Absolutely, man.
This is stuff you see
on TV.
Yeah, for real.
That you wish
would happen to you,
but we can go to college.
Yeah.
I don't have to worry
about anything right now.
Jocelyn,
the time I spent
with you was
unbelievable.
Wow.
It took me nine years
playing clubs
to get recognized.
And your time is now.
Thank you.
You know,
and when I started this journey,
I wanted to,
I came out here
to find musicians I wanted to help.
I didn't expect to find you.
I didn't expect
to be blown away
the way I was.
And my goal
is to get you a record deal
with a major
to make you a superstar.
Wow.
Yeah.
To help you with everything,
just to get you started,
I'm going to give you $10,000
to hone your craft.
And on top of that,
when you're ready,
I'm going to personally
walk you into
the president
of the Universal Music Group.
And I want you to wow them
the way you wowed me
with your song.
This is beautiful, man.
It is.
It is beautiful.
That's the thing,
is it's crazy great.
It's amazing.
You know, I...
You know, when you get
your record together,
I want you to come play shows,
a couple shows with me.
You know, just so I can
watch you play.
And I want nothing in return
but to someday go,
I know her.
I know Jocelyn.
So happy that
all the time's practicing
in my bathroom
and just working really hard.
It's all going to pay off.
Give me a hug.
We're going to be talking
real soon.
This is a very
big life-changing day for me.
I'll talk to you soon.
I will talk to you soon.
Real soon.
Hello?
Hey, Mom.
Do you know Hootie
and the Blowfish?
Yes.
Darius is taking me
to Universal Music Group
and having me sing
to the president.
Are you serious?
Yeah.
Wow.
Oh, my gosh.
I don't believe it.
Yeah, I know.
It's crazy, isn't it?
Tamir.
What you have inside of you
was just wonderful to watch.
You were something special.
Wow.
I still see your eyes
They're just like mine
And I'll show you
When I asked you
what were your dreams,
you said,
I don't dream anymore
because I'm living my dream.
Yeah.
When you said that,
it made me think
that's exactly where I am.
I'm living
in the middle of every dream
I've ever had.
Yeah.
And I came here
to help people
live their dream.
I mean,
you have something special.
Your voice is special
and your songwriting
is so real
and I want you to be able
to share your music
with the world.
So I want you
to write a record
and I'm going to give you
$20,000 to make the record.
Oh.
Wow.
Is this really
happening right now?
This is real, man.
This is real.
What?
This is real.
You did so much for me
and you touched me so deeply.
I want to give you
another $20,000
because you're not going
to stop busking
and I don't want you to.
But that's money
that can help you
take time off
to write songs
and make the record.
You know,
I hope you will accept
that from me.
Yeah.
I mean,
what?
No.
No strings attached.
Nothing,
no strings attached.
Oh, this is so much.
I want to be there for you.
I want you to have my number
and me to have your number.
Give me your number.
Oh, I will.
Oh, trust me, man.
I will.
You will have my number
before we leave here today.
Uh-oh.
I'm going to be there
in your corner
trying to help you
take a step
every time you want to.
And you know,
that classical guitar
you play with
those classical strings,
it sounds great,
but I think
when you're standing
out there on the street,
this right here
is going to sound
a lot better, man.
That's a Gibson Hummingbird.
What?
I play that.
Those are the best-sounding
guitars in the world.
Wait, what are you saying?
That's yours, man.
Oh, my goodness.
Are you serious?
Oh.
I just have $40,000
strapped into my lap.
I can make an album,
music that I've been
wanting to make,
but I can't afford it.
You deserve that.
I don't want you to have that.
Thank you.
You know,
like every Father's Day,
I would just,
I would cry
because my dad was away,
he was locked up.
I can't believe
this is happening.
To have someone,
a man,
to send my music to
or just talk to
is priceless.
Like, you can't even,
it's irreplaceable,
you know,
to have that.
I got a rhythm in my heart
that I can't fight
Got me so bad
I don't know what to do
But I really want to be
with you
This whole journey's
brought me back to
all those great moments
I had before
any of the success.
These original?
Yeah.
Doing all this is just
reminding me
that it's not about
money or fame
or hit records,
it's about the music.
You know,
because you love it.
You have the passion,
you have the love of music.
I love that,
and that's what it's all about.
My life has changed
Ever since today

