Stand-Up Comedy Is HARD: All Around Losing (Episode 2)

reveres Louis C.K. even though he’s a fat, bald, middle-aged
dude who talks about his dick on stage. That’s the great thing about
stand-up comedy. All that matters is that
you make people laugh. And like a lot of people who
think they’re funny, I’ve always believed that maybe I
could do stand up, too, if I only took a shot at it. That was my first mistake. My name is Harry, and
I’ve been a loser for most of my life. I thought I was done with my
awkward phase when Vice hired me to write about politics,
culture, and other important world affairs which should make
me cool, but it doesn’t. I’m still just a weird kid
who creeps people out. This is “All Around Losing”
with Harry Cheadle. So I’m out here in front of the
Sidewalk Cafe where they have an open mic every night. I am incredibly nervous
right now. I’ve written my set
list on my hand. As you can see, it goes
from porn to sex-ed to Obama at the end. And I don’t think this is going
to go well, but I’m also confident this is going to go
well because I’m just a massive contradiction. But here I go. -Make some noise for Harry
as he comes to stage. HARRY CHEADLE: You guys are
really attractive out there. The terrifying part of doing
stand-up is when you get to the punch lines. Are people going to laugh? Are they going to boo? Are they going to know I have
no business being on stage? There almost has to be something
wrong with you to expose yourself to a situation
like that. But surprisingly, the crowd at
the Sidewalk laughed at all the right times. [LAUGHTER] HARRY CHEADLE: Sex is gross. Sex is just the two weirdest
parts of your body just colliding over and over. [LAUGHTER] HARRY CHEADLE: If I went back
in time and talked to my 11-year-old self about the sex
I was having, he’d be like, that’s gross. And he’d be right, and I think
I’d probably go to jail for talking to an 11-year-old
about sex anyway. [LAUGHTER] Even the guy who heckled
me was polite. I will, and I have a whole
bunch of jokes about sex. I don’t know. I guess I’m going to keep going
on with the jokes I have in my head, if you don’t mind. Oh yeah, let me talk more
about sex for a second. Maybe I was just good at this? Thanks, you guys have
been great. [APPLAUSE] -Harry. It’s his first time,
everybody. HARRY CHEADLE: I didn’t do too
badly my first time on stage which was surprising because I
blacked out and have no memory of the experience whatsoever. When I came to, it was already
time for my second show at Cha Cha’s Comedy Club. On my way inside, I ran into Cha
Cha himself, a spherical, Hawaiian-shirted, comedy
guru who’s been in the business for decades. CHA CHA: How long you’ve
been doing this? HARRY CHEADLE: I’ve been doing
like a week, honestly. CHA CHA: A week, right? -Please put your hands together
and welcome to the stage Harry Cheadle. HARRY CHEADLE: When I have sex
it’s like I’m a blind man in a bouncy castle trying
to kill a frog. It’s not clear how that blind
man got in that situation, like it doesn’t make any sense,
like why is he here. He doesn’t have the skills
or the tools necessary to complete this task. There are people out there who
say like, oh, sex is this great, spiritual, life-affirming
thing. Those people have not had sex
with me because when I have sex it’s not a spiritual
experience. My second time out,
I died on stage. Though actually dying is
probably way less painful than what I went through. All Cha Cha’s Strom Thurmond
style comedy coaching did was distract me with thoughts
of Mexican whorehouses. Before I did this again, I
would need to get drunk, really drunk. I’ve heard that alcohol is
supposed to make you more confident, but instead, eh,
fuck, let me try that again. Have you heard that alcohol
is a good way to calm your nerves? It’s not. -Let’s everyone please
give a warm welcome to Mr. Harry Cheadle. HARRY CHEADLE: So you guys are
really attractive for the open mic audience, anyway. Oops, I’m gonna take
this mic off. The worst thing isn’t
not getting a laugh. Who’s going to get
laid tonight? Anyone? This is going to
go really bad. The worst thing is knowing that
everyone out there knew you were trying to get a laugh,
and that you failed, and that you’re not funny. Sex is disgusting. I’ll wiggle it around
in there for awhile. And like, oh yeah, that sounds
great, let do that. And that’s awesome. Actually, the worst
thing is that you keep going after that. This sex material is terrible. That was my impression
of trying to do sex material, everybody. It failed. That was good. Someone liked my material
on bombing. Yeah, let me just talk more
about how bad I suck. That would be great. Man, you know, always. And then but women, man. Yeah, that stills needs
a little bit of work. Thank you, guys. You’ve been great. The best part is when
it’s finally over. -Alright, Harry Cheadle,
everybody. HARRY CHEADLE: This stuff
is the most difficult thing I’ve ever done. And if anyone can get any laugh
from anybody in front of a crowd, that’s like amazing. And anyone who does it for
a long time deserves your respect or your pity,
I don’t know which. Jesus Christ. [MUSIC PLAYING]

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