Name: Sean Penn Never Met Madonna | David Letterman
Uploaded: 2025-05-19T15:01:41.000Z
Description: Watch the stand-up comedy video 'Sean Penn Never Met Madonna | David Letterman' from Letterman on Comedy Buff. Published 2025-05-19. Transcript available.

Watch the stand-up comedy video 'Sean Penn Never Met Madonna | David Letterman' from Letterman on Comedy Buff. Published 2025-05-19. Transcript available.

how you doing thank you very much for being on the show would you like a soda i'd
like to see
him run again yeah it's pretty exciting wasn't it right by the dressing room
yeah uh you know i
remember a long time ago you and i lived in the same neighborhood yeah i saw
you in the bank once
yeah you know i used to go to the market and uh i was living with a girl in a
house out there and
a couple of dogs at the time and and it would always be an exciting day or week
for us when
we would see you pull up at the market in your pickup truck well i can match
that because i i
still use your house as a tour stop when i bring people around my old
neighborhood dave used to live
there yeah yeah um you know let's see uh not too long ago your girlfriend the
mother of your son was
here child uh daughter daughter and your brother has been here a couple of
times yes that's right
michael yeah uh your ex-wife has been here a couple times yeah
now is is what there was a time when when i would occasionally make jokes about
the difficulties you were having on the show and i was wondering if the reason
if the reason you hadn't been on the show before now was because you were you
were mad at me
no no no the reason i hadn't been on the show just because i think that
that to talk about the business of acting is something difficult to articulate
was
it's much more tangible with directing but in terms of that i felt vindicated
when i saw the
marlon brando interview and he did an imitation of you oh yeah what did you
what was that all about
martin brand or marlon brando was making fun of me was that what that was well
it's you know still
part of the highest form of flattery now that he did you yeah i guess i guess
so uh now i want to
talk about the directing and stuff in a second but let's let's go back to that
period of your life if you
don't mind you were having a lot of trouble i mean a lot of trouble and in fact
some of the trouble
took you away for about a month was that right you were actually you were in
the the la county
lockup for 30 days or so right yeah now when you look back on that time of your
life how do you regard
that what does that seem like to you now do you think i made some mistakes and
i can learn from
those or it was just bad luck or what was i think i mean what does it seem to
you now that that was
well i i can't say that i have any particular regrets about any of any of that
time period and
and in retrospect it was a fairly short time period when it was so uh uh viewed
by the press yeah yeah
they came down on it but um uh just just one more transition in life i suppose
now do you do you ever
see yourself going through that kind of trouble again oh god i hope not yeah uh
but it is the kind of thing
where where you get into a fight with one person and then all of a sudden
situations are presented that
would not have been there had the first one not occurred yeah there's a
snowball effect to any of
that stuff and particularly when you get caught up in in on any level in the uh
legal system as it were
then uh once you've got some uh a tail on you then yeah tend to get in trouble
yeah have you yourself
ever been beaten up yeah really you have been beaten up oh yeah yeah how many
fights do you think you've
been in as an adult now i'm not talking about high school stuff but as an adult
not counting the one here tonight
i'll tell you why i'm asking i was in two fights yeah and i lost both of them
and they both they just
scared me silly and i said to myself that's it for fighting well i think uh if
fighting is an upsetting
experience yeah do you feel badly after you've had or after you would have one
of those even if it's
justified you feel nauseous afterward even if you win yeah but um if you have
any sense of caring about
people at all you do yeah um but but a lot of all a lot of that stuff was
fairly i mean i'm not gonna
tell you i'm going to heaven but i would say that a lot of that stuff was
pretty well blown out of
proportion yeah i can imagine what what little i know of life in the public eye
i can imagine that
it was blown out of proportion um and and when you it looks like you have
gotten the better of a person
than everybody they're going to be lawsuits and it's going to be in the
newspapers but if you're
ever in an encounter where you're on the short end of things you never hear
about it right
yeah i don't tend to be one to get into lawsuits that i insigate yeah yeah
waste of time all right
well anyway i i appreciate your indulgence on this topic but i think it people
are you know curious
about that sort of thing yeah um and and as far as madonna goes do you have you
seen her lately do you
have a friendly relationship with her now or uh well i'll tell you a secret the
fact of the matters
as i was talking about before uh things being blown out of proportion that was
on the rumor she and i
never met
i knew it had to be something like that now when did you uh what was the behind
the decision to stop
acting have you stopped acting all together or just stopped acting temporarily
you know i'd say uh you know never say never but uh i i just got to a point
where i realized i wasn't
enjoying it at all and and then uh having directed a movie had such a good time
doing that that i think
i'll try and stick with it yeah what what about acting do you think you began
not to enjoy so well
i just found it sort of uh emotionally torturous i think all actors have a
different way of working
depending upon who the who the actor is and there's some wonderful actors for
whom it's a very
accessible process and for me it was like tearing oneself apart do you think
that there would have been an
easier way for you to accomplish the same quality of work i don't think so i
think what you latch on to
and the thing that that you go after and for me it was acting with the other
are the challenges that
are most fascinating to you and though and it was and then making the choices
that you make as an actor
is then uh the way to achieve those choices uh was very difficult for me and
you don't want to change
change them because it's difficult now when you're directing this movie uh indian
runner and and you
see a scene transpiring and you think to yourself well that's good but if it
were me i i would have
i would have behaved a different way in front of the camera and then do you
think oh damn i'm sorry i
made this choice no well i i have a hell of a cast in the movie and they uh
were much more suited for
the parts they were playing than i would have been um so no i think that i
responded less as an actor
and more as a writer most of the time watching this stuff and being excited and
surprised by what i was
seeing i generally have a i mean when i went into it i went to the bottom line
in terms of the
storytelling of the movie and uh and then tried to let the uh the other people
be it crew or cast and
make the embellishments for me yeah but isn't there uh some part of it like if
it were me if i was an
actor or something maybe once a week or once a month i'd race home and i'd
close the door
and i'd just scream as loud as i could i'm in a movie you know it would it
would be exciting to know
that people are paying money and sitting there eating stale popcorn looking at
my goofy face on
the big screen that would be now now granted that's not all there is to it but
that would be
a thrill now was there a certain part of you that uh you're are you going to
miss that well i guess you
could always go back to it can't you well i think for me it was a little bit
different it was it was
going home once a week and saying i'm in a movie
i see so it's just kind of the other side of that
all right let's talk about the uh the movie that you have uh directed here what
what should we know i
guess we're going to look at a clip of it here uh well first of all let's talk
about how you got to
be from an actor to writing your own script to getting to direct your movie i
mean people know
you're a great actor but that doesn't necessarily follow that oh great we can
trust him with a 10 12
15 million dollar budget so how does that happen that you get to be the
director here
well i had been writing for a long time and then when i decided i wanted to
direct something i wrote this
particular one specifically to direct it um it it happened in a much easier
than it than than it
might again or might have in any other time and it had really to do with a
producer named tom mount and
don phillips who uh don initially read the screenplay and and wanted to do it
brought to tom and he was
in a position to finance it and it just went uh but that's unusual i think it
just went to the right
people at the right time yeah and and because it's unusual because it's the
first time was there
added pressure for you did you did you ever really really get concerned about
oh man what have i done
here i've stepped off a curb no i i was confident that in terms of the story
that i wanted to tell i
had the images in my head then i knew how to to achieve them whether or not
that translates to another
story but uh and that was really the only uh prerogative in a sense and and
this is based on the
the bruce springsteen song um highway patrolman highway patrolman and you heard
the song once and and all
of a sudden you think to yourself that this works out to be a pretty good film
is that essentially
how it goes well the song hit me on it was a very strong visceral level and i
thought that
that it was cinematic in a in a way and then over the years the the pictures
just coming kept
coming to the head and eventually it added up to what i would have considered a
long form and so
i banged it on a typewriter and went and shot it okay okay and you had no
trouble getting the rights
from bruce to do this well i had i wrote the script on spec without asking
ahead of time because i know
that he had been approached many times for the ideas of things and i thought it
would be a better
situation to just go ahead and take the chance i wanted to write it whether i
got it done or not
and so i went and so when he was in a position to approve or disapprove of it
being done
i was able to give him a script that he could make a decision and he thought
okay yeah yeah i'd
like to be in a film with him he and me me and bruce maybe a buddy picture
me and bruce joined the army something like that um so sean now we're gonna see
uh we gonna look at
it now okay do you know we're gonna take a look out here from the film yeah it's
a it's a scene that
towards the towards the end of the story where the uh older brother is uh
confronted his younger brother
on uh some some uh issues of weakness in him that he thinks that he recognizes
this is the essential
conflict a good brother and a bad brother right in a black and white sense yeah
okay all right here we
go indian runner uh directed by sean penn yeah there you go let's see here
september 20th the film opens all across the country new york l.a how does it
work no it's a
they call a platform release where it's two theaters in los angeles two in new
york one in
toronto and then two weeks later 12 more cities and then it's up to the movie
are you nervous now about this no i've taken it to a couple of festivals at
this point so
so i the the big sitting in a theater and watching it with a group for the
first time has already
happened and i you know i certainly hope the best for it but uh i'm a little
bit on with it well good
good luck and congratulations and uh again thank you very much for being here
tonight i really really
appreciate it so we look forward to it for a long time sean penn kids we'll be
right back