LYDIC: What makes a great leader?
Is it courage?
Compassion?
Charisma?
Or is it an integrity and confidence
that just leaks out of their pores?
A calming strength that drips from every orifice.
And the way they give their blood, sweat
and other bodily fluids to make the world a better place.
Since the 2016 election,
Rudy Giuliani has been a national leader,
spreading his patriotic message at political rallies...
Let's have trial by combat!
-...landscaping company parking lots... -(horn honks)
...and arenas across this great nation.
-America! -(cheering)
LYDIC: But how did he become the man
and/or man-like creature he is today?
This is the Daily Showography of Rudy Giuliani:
Oozing Greatness.
-(crying, screeching) -Rudolph William Louis Giuliani
was born in 1944
in East Flatbush, New York.
His father was an alleged mob enforcer
who did time at Sing Sing for armed robbery.
He would tell me,
never take anybody else's money,
make sure you always pay for things.
I mean, he wanted to make sure that I didn't...
make the same mistakes that he believed he had made.
LYDIC: It was an inspiring message from a father--
come up with your own original crimes.
And he would.
To keep Rudy away from New York City's criminal element,
the family moved to the suburbs.
GIULIANI: I can remember as a youngster
that my father would sometimes threaten me
with putting me in public schools
if my behavior didn't improve,
and that was a very frightening thought.
But I was a product of Catholic education.
And it instilled in me from a very early age
a desire to be a priest.
LYDIC: That's right. Giuliani almost became a man of the cloth
instead of a man of... sweaty handkerchiefs.
Ultimately, he chose not to pursue the priesthood,
deciding instead to marry his childhood sweetheart,
who also happened to be his second cousin.
And while, today, that may be seen as weird,
back then, it was seen as super gross.
After graduating law school, Giuliani began
his meteoric career, quickly rising
to the third highest position
at President Reagan's Justice Department.
He was the youngest person ever to hold the job,
but he was already sporting the combover
of a man twice his age.
Soon, Rudy was U.S. Attorney
for the Southern District of New York.
Rudy wasn't afraid to take on criminals or to give lots
of press conferences about how he took on criminals.
GIULIANI: Well, I think, uh, five or six or seven years ago,
nobody would have believed it was possible
to convict the head of the Sicilian mafia and
have him sitting in the Metropolitan Correction Center.
LYDIC: He loved the camera, and the camera
just wanted to be friends.
But soon, taking credit for arrests wasn't enough.
He had to pretend to make the arrests himself.
I bought crack.
I had a female D.E.A. agent
who was, like, theoretically my date,
and we went up, and we purchased crack in Washington Heights.
LYDIC: Now that's what I call going undercover.
Tell me you don't think he smoked crack
before picking out that outfit.
With his crimefighting career burning hotter
than totally normal lust between second cousins,
Rudy set his sights on elected office.
He first ran for mayor of New York in 1989,
but he didn't quite have the name recognition
he needed to win.
GEORGE H.W. BUSH: I would like to commend
Republican candidate Rudolph
Gia-Gia... Giaulani. Rudy.
-(laughter) -Sorry about that.
LYDIC: Wow. Tough break for Rudy Geo... philly... uni.
Four years later, Rudy tried again, and this time,
he had the perfect foil to rally his voters against--
New York's first Black mayor.
Denouncing David Dinkins as soft on crime,
Giuliani led off-duty police officers
in a peaceful protest.
-ALL: He's got to go! -NEWSMAN: And then, minutes later,
thousands of cops stormed through the barricades
and ran on top of cars
as they charged the stairs of city hall.
LYDIC: Okay, it was a peaceful-ish protest.
At least hyping up a crowd to storm a government building
would be good practice for him.
So, through sheer charisma, and just a little hint
of police intimidation,
he finally became Mayor Geohani.
Sorry. Giuliani.
Over the next decade, Giuliani took New York City
from a gutter toilet of violence and sex and piss
and turned it into a clean and safe utopia
with ample magazine jobs that allowed young women
to live in giant apartments
with walk-in closets and so many shoes.
Under Giuliani, the New York Police Department
pioneered some of the most iconic anti-crime tactics
of the era, like stop and frisk.
Broken windows policing.
Sexual assault with a broom handle.
And shooting an innocent guy so many times
Bruce Springsteen wrote a song about it.
♪ 41 shots ♪
♪ Lena gets her son ready for school ♪
LYDIC: And Giuliani didn't just go after criminals,
he went after all poor people
in the most hilarious ways.
Look at you-- lying there like that.
Don't you have any dignity?
Lying on your butt all day collecting welfare?
(growling)
LYDIC: Yeah, I think he was still buying crack.
Giuliani was bringing glamour back to New York City.
And if he was making a few enemies,
he was also making some good friends.
You know, you're really beautiful.
(high-pitched): Oh, you dirty boy, you, oh, oh.
LYDIC: Finally, Rudy found a disguise
that managed to fool someone dumber than a crack dealer.
By now, Giuliani was ready to shake things up.
He dumped his second wife at press conference
without telling her first.
In many ways, we've, um, grown-grown to live
independent and separate lives.
LYDIC: Leaving her to respond with own statement
about how he was a cheating ho.
For several years, it was difficult to participate
in Rudy's public life because of his relationship
with one staff member.
LYDIC: Rudy moved out of the mayor's mansion
and crashed with some friends--
a gay couple and their pet shih tzu--
while running a losing Senate race against Hillary Clinton.
Honestly, his life was a lot simpler
when he was just banging his cousin.
And then, just as his term was coming to an end,
Rudy Giuliani found himself right where he needed to be.
Tomorrow, um, New York is gonna be here
and we're gonna rebuild
and we're gonna be stronger than we were before.
9/11 gave Rudy his big promotion to America's mayor.
-GIULIANI: America! -LYDIC: And that's
when the party started.
DAVID LETTERMAN: Ladies and gentlemen, please welcome,
uh, Mayor of New York City, the Honorable Rudolph Giuliani.
(crowd chanting): Rudy! Rudy! Rudy! Rudy! Rudy!
LYDIC: Yes, no one rose to greater prominence
after 9/11 than Rudy Giuliani, except maybe bin Laden.
By 2008, Giuliani was finally confident enough
to admit he was bald and to make a play
for the highest office in the land.
NEWSWOMAN: Rudy is in. America's mayor
now wants to be America's president.
LYDIC: Anyway, he came in sixth in Iowa
and was out of the race by February.
By the time the 2016 election year came around,
Giuliani had realized he didn't need to be president.
He could just be friends with one.
It was a win-win friendship.
Trump gave Rudy the power he was longing for,
and Rudy made Trump look attractive by comparison.
As Trump's BFF, Rudy was really going places,
even if he didn't always seem to know where he was.
From the top to the bottom,
from the middle to the side.
LYDIC: The next four years were a whirlwind of campaigning,
lawyering, cheerleading,
extorting, treasoning and insurrectioning.
By the time it was over, Giuliani lost his law license,
several gallons of hair dye,
a variety of electronic devices seized by the FBI
and most of all, his dignity.
Hi. It's Rudy Giuliani, and I'm on Cameo.
In a pay-for-play scheme!
LYDIC: But Rudy is still oozing on,
enjoying life to the fullest.
Maybe even too much.
I don't think I've ever done an interview drunk.
I-I have, uh, sometimes... I mean, I drink normally.
I like Scotch. I drink Scotch.
NEWSWOMAN: So you do not believe
that you have a drinking problem?
(chuckles): I... No, I don't only believe it. I know I'm not.
I know Prince Andrew is very, uh, questionable now.
I never went out with him.
Ever.
Never. Never had a drink with him.
Never was with a woman or a young girl with him.
Ever, ever, ever.
One time, I met him in my office,
and one time when we had the party.
Right, Bernie? You were there.
LYDIC: Yes, whether he's standing tall through 9/11
or a blood alcohol level of .911,
Rudy Giuliani is a born leader
making his mark wherever he goes,
one that no stain remover can ever take away.
(cheering and applause)