the longest-serving late-night talk show
host in history has had some memorable
moments over the years ladies and
gentlemen this is not a promo this is
the actual show welcome to watchmojo.com
and today we’re counting down our picks
for the top 10 David Letterman TV
moments number 10 things that sound
creepy when said by John Malkovich I put
my jammies on all by myself mom made for
this list we’re looking at the best
moments from David Letterman’s
late-night shows and are including both
his time on NBC and CBS meaning both
Late Night with David Letterman and Late
Show with David Letterman we’re looking
for specific incidents however and are
not including recurring segments like
the top 10 lists although we at
WatchMojo would like to give a special
thanks to Letterman for this format
number ten monologue after 9/11 to the
Late Show this is our first show on the
air since of New York and Washington
were attacked and I need to ask your
patience and indulgence here because I
want to say a few things the United
States and especially New York City was
in no mood for comedy following the
terrorist attacks on September 11th 2001
Letterman was the first late-night
comedian to return to the air and gave
an emotional monologue to open his first
show back they had a rally for New York
City and not just a rally for New York
City but a rally to raise money to raise
money for New York City and and if that
doesn’t tell you everything you need to
know about the spirit of the United
States and I can’t help Letterman was
visibly distraught but gave a heartfelt
speech that praised then Mayor Rudy
Giuliani the police and fire departments
for myself and everybody else not only
in New York but everywhere is that we
never ever take these people for granted
absolutely never take them for granted
he ended by calling New York City the
greatest city in the world if you didn’t
believe it before you can absolutely
believe it now New York City is the
greatest city in the world which would
become the tagline of the show I I think
these are great moments on television
well thank you I well thank you I don’t
know what to say beyond that number nine
Paris Hilton after jail I Love New York
New York City is exciting though isn’t
it I was born here yeah yeah good for
you
how’d you like being in jail Letterman
can be pretty tough on his guests and
even made Lindsay Lohan cry at one point
stop yeah she’s tearing up a little bit
god bless you although Paris Hilton
didn’t cry she was visibly angered by
Dave’s constant questions about her time
in jail tell us what it now looking back
looking back on that experience what
have we learned what can you tell us
what what’s different about you
forward as you look back Paris allegedly
believed she’d been invited on the show
to talk about her perfume and her new
film but instead was grilled by
Letterman about what jail was like
including what the meals were and if
they had locked up her friend Nicole
Richie as well they locked up here a
friend Nicole she was only in for a
short period of time when she how could
she was only in for like 45 minutes how
did that work how can somebody only be
in for 45 minutes number 8
Dave admits to adultery well more or
less
while Letterman was never afraid to make
fun of himself and his life on air he
kept the details of his personal life
relatively private the creepy stuff was
that I have had sex with women who work
for me on this show that all changed in
October of 2009 when he confessed on-air
to having had sexual affairs with female
members of his staff would it be
embarrassing if it were made public
perhaps it would perhaps would this
especially for the women perhaps more
shockingly he gave details of an
extortion attempt against him from a man
who was seeking two million dollars or
he would tell the public all the details
of Dave’s sexual escapades the idea is
is if they believe in fact a crime has
been committed then they issue a warrant
and that’s exactly what happened and a
little bit after noon today the guy was
arrested number seven Farrah Fawcett
spaced out what kind of things do they
say to you when they see you yo looking
good yeah yo yeah so yeah right you know
that New York where they just say yes
Farrah Fawcett is not the first
celebrity to try to hang on to success
but she may have spent too much time in
the tanning bed before this interview
yeah
faucet tolls long nonsensical stories
that left everyone including Letterman
incredibly confused and there are places
where the wall right the wall what is
that the thing the interview sparked
rumors that faucet was on drugs or drunk
though that’s really dope although it
was later suggested that she was
attempting to play the ditzy blonde to
promote Playboy magazine we’ll let you
decide that’s one that’s more and you
could just cover that right sure cover
the bat how long did it take you to get
the paint off number six
Madonna dropping f-bombs put on an hour
just sitting around smoking cigars
swapping recipes Letterman isn’t afraid
to antagonize his guests and this
interview with Madonna may be the
perfect example let’s go kiss a guy in
the audience they’ve set the stage by
introducing her as having slept with
some of the biggest names in the
industry and Madonna retaliated by
saying she was only there because there
wasn’t a Knicks game on she then
proceeded to drop the f-bomb 14 times I
tell you what we were gonna do a
commercial and we’re gonna wash her
mouth out with soly underwear claim that
she gave Dave a pair of her underwear
and made countless sexual innuendos Dave
just slobbered all over my car you asked
me to light it for and I thought I was
doing the gentlemanly class I’m ever
gonna get to kissing you including a
joke about NBA players and the
microphone microphone is really long
speaking of the NBA number five Johnny
Carson’s final appearance Johnny could I
have the top ten list Jay Leno may have
landed The Tonight Show gig but it was
Dave who got the last laugh when he
secured Johnny Carson’s final TV
appearance in 1994
Carson who first appeared on Letterman
in 1985 walked on stage to thunderous
applause from the audience
Letterman gave him the host chair and
for a second it seemed like Carson would
reclaim his throne he then shook his
head and as all legends do walked off
into the sunset it’s still a little warm
I wish a little that would rub off on me
Wow number four Andy Kaufman gets
slapped I don’t want to sit out here and
pretend that I’m friends with this guy
because I think he’s a wimp with Andy
Kaufman it was nearly impossible to tell
if something was real or staged Kaufman
appeared on Letterman with wrestler
Jerry Lawler who had injured Kaufman’s
neck in a wrestling match Kaufman
demanded an apology from Lawler because
of the injury while Lawler mocked
Kaufman’s neckbrace Lawler eventually
had enough and slapped Kaufman so hard
he fell out of his chair
you’re full of my friend I will
sue you for everything you have I’ll sue
your ass Kaufman unleashed a verbal
tirade on Lawler and threw a cup of
coffee at him
staged or not this is definitely one of
the more memorable moments in television
history
thanks to the studio audience we’re
putting up with this tonight I think
we’ve learned a little something about
human nature haven’t we number three
Joaquin Phoenix’s bizarre interview I
will just say right off the top here
you look different than I remember it
okay so this was a stunt performed by
Joaquin Phoenix and Casey Affleck for
the film I’m still here it’s time for me
to end this game with a brand-new star
coming to you live direct of you tear
out my spleen it’s none other than the
one and only walkie regardless this was
one of the strangest moments in the
history of Letterman’s career and it
showed just how funny but ruthless the
late-night host could be once he got his
hands on you I’ll come to your house and
chew gum to be fair Phoenix was asking
for it with his untamed hair lumberjack
beard and dark sunglasses what well can
you tell us about your days with the
Unabomber Letterman hammered Phoenix
asking him about his time with the
Unabomber and mocking his musical career
or thanks high praise coming from you he
ended the interview with the perfect
line and Joaquin I’m sorry you couldn’t
be here tonight
number two Crispin Glover nearly kicks
Dave I notice you have something there
in the case I I knew that this was gonna
happen in Phoenix may have been taking a
page out of Crispin Glover book who
appeared on Dave’s late-night show in
1987 and nearly ended up kicking
Letterman in the face you seem to make
me sound a lot weird and I’m just I’m
strong you know I’m strong I can arm
wrestle
this interview was bizarre and
uncomfortable as Glover read random
clips about himself from the newspaper
whoever was pinstripe and greased up for
the occasion
and pressing the girl things who are
trying to get next to him guess some
people are turned on by Brylcreem yeah
well perhaps more miraculous was that
Letterman allowed Glover to ramble on
incoherently okay I’m gonna go check on
the top ten until Glover almost kicked
him in the face
at which point Dave walked off the set I
would love to chat it more with Crispin
Glover but I just understand he had a
cab to catch and well
traffic this time a night here in
Midtown is pretty brutal before we
unveil our number one pick here are a
few honorable mentions for this to
happen for me to be in a comedy club and
flip out and say this crap you know I’m
I’m deeply deeply sorry while I was gone
I had quintuple bypass surgery on my
heart Oh
plus I got a haircut it isn’t where a
bad country bushes and evil lie I didn’t
say we were country I really didn’t say
he was an evil liar you’re putting words
in my mouth just the way you put
artificial facts in your head right that
was some entrance are you all right I
went to the other place and it turned
out not to be congestive heart failure
yeah no and what was the diagnosis it’s
it’s lung cancer that’s spread that’s
tough
well that means you better get your dry
cleaning done unspecial number one
drew Barrymore flashes Dave would you
like me to do dance for you wait are we
sure this was the cute innocent little
girl from et this interview started off
perfectly normal but things heated up
when Dave mentioned Drew’s recent
appearance at a club where she stripped
it’s called the Blue Angel it’s really
really cool yeah
forty-four Walker Street yeah well you
know what that’s not I know where that
is everyone including Dave was stunned
at what happens next as Barrymore jumped
onto the desk and lifted her shirt up
giving Letterman a full view I wish more
of our guests would consider that sort
of thing
Courtney Love would attempt to replicate
this act in a future interview
but it didn’t come close to reaching the
same heights as Barrymore’s Act which
Letterman still talks about to this day
it’s it’s it’s my birthday you’ve made
it amit of gasha was fun yeah that was
very nice of it it’s always a pleasure
to have here do you agree with our list
what’s your favorite David Letterman
moment what are you doing here I’m gonna
I’m doing a show I’m doing a TV show
here I thought I thought you were dead
for more great top 10s published every
day be sure to subscribe to
watchmojo.com thank you very much for
joining us tonight we’ll see you
tomorrow good night everybody
host in history has had some memorable
moments over the years ladies and
gentlemen this is not a promo this is
the actual show welcome to watchmojo.com
and today we’re counting down our picks
for the top 10 David Letterman TV
moments number 10 things that sound
creepy when said by John Malkovich I put
my jammies on all by myself mom made for
this list we’re looking at the best
moments from David Letterman’s
late-night shows and are including both
his time on NBC and CBS meaning both
Late Night with David Letterman and Late
Show with David Letterman we’re looking
for specific incidents however and are
not including recurring segments like
the top 10 lists although we at
WatchMojo would like to give a special
thanks to Letterman for this format
number ten monologue after 9/11 to the
Late Show this is our first show on the
air since of New York and Washington
were attacked and I need to ask your
patience and indulgence here because I
want to say a few things the United
States and especially New York City was
in no mood for comedy following the
terrorist attacks on September 11th 2001
Letterman was the first late-night
comedian to return to the air and gave
an emotional monologue to open his first
show back they had a rally for New York
City and not just a rally for New York
City but a rally to raise money to raise
money for New York City and and if that
doesn’t tell you everything you need to
know about the spirit of the United
States and I can’t help Letterman was
visibly distraught but gave a heartfelt
speech that praised then Mayor Rudy
Giuliani the police and fire departments
for myself and everybody else not only
in New York but everywhere is that we
never ever take these people for granted
absolutely never take them for granted
he ended by calling New York City the
greatest city in the world if you didn’t
believe it before you can absolutely
believe it now New York City is the
greatest city in the world which would
become the tagline of the show I I think
these are great moments on television
well thank you I well thank you I don’t
know what to say beyond that number nine
Paris Hilton after jail I Love New York
New York City is exciting though isn’t
it I was born here yeah yeah good for
you
how’d you like being in jail Letterman
can be pretty tough on his guests and
even made Lindsay Lohan cry at one point
stop yeah she’s tearing up a little bit
god bless you although Paris Hilton
didn’t cry she was visibly angered by
Dave’s constant questions about her time
in jail tell us what it now looking back
looking back on that experience what
have we learned what can you tell us
what what’s different about you
forward as you look back Paris allegedly
believed she’d been invited on the show
to talk about her perfume and her new
film but instead was grilled by
Letterman about what jail was like
including what the meals were and if
they had locked up her friend Nicole
Richie as well they locked up here a
friend Nicole she was only in for a
short period of time when she how could
she was only in for like 45 minutes how
did that work how can somebody only be
in for 45 minutes number 8
Dave admits to adultery well more or
less
while Letterman was never afraid to make
fun of himself and his life on air he
kept the details of his personal life
relatively private the creepy stuff was
that I have had sex with women who work
for me on this show that all changed in
October of 2009 when he confessed on-air
to having had sexual affairs with female
members of his staff would it be
embarrassing if it were made public
perhaps it would perhaps would this
especially for the women perhaps more
shockingly he gave details of an
extortion attempt against him from a man
who was seeking two million dollars or
he would tell the public all the details
of Dave’s sexual escapades the idea is
is if they believe in fact a crime has
been committed then they issue a warrant
and that’s exactly what happened and a
little bit after noon today the guy was
arrested number seven Farrah Fawcett
spaced out what kind of things do they
say to you when they see you yo looking
good yeah yo yeah so yeah right you know
that New York where they just say yes
Farrah Fawcett is not the first
celebrity to try to hang on to success
but she may have spent too much time in
the tanning bed before this interview
yeah
faucet tolls long nonsensical stories
that left everyone including Letterman
incredibly confused and there are places
where the wall right the wall what is
that the thing the interview sparked
rumors that faucet was on drugs or drunk
though that’s really dope although it
was later suggested that she was
attempting to play the ditzy blonde to
promote Playboy magazine we’ll let you
decide that’s one that’s more and you
could just cover that right sure cover
the bat how long did it take you to get
the paint off number six
Madonna dropping f-bombs put on an hour
just sitting around smoking cigars
swapping recipes Letterman isn’t afraid
to antagonize his guests and this
interview with Madonna may be the
perfect example let’s go kiss a guy in
the audience they’ve set the stage by
introducing her as having slept with
some of the biggest names in the
industry and Madonna retaliated by
saying she was only there because there
wasn’t a Knicks game on she then
proceeded to drop the f-bomb 14 times I
tell you what we were gonna do a
commercial and we’re gonna wash her
mouth out with soly underwear claim that
she gave Dave a pair of her underwear
and made countless sexual innuendos Dave
just slobbered all over my car you asked
me to light it for and I thought I was
doing the gentlemanly class I’m ever
gonna get to kissing you including a
joke about NBA players and the
microphone microphone is really long
speaking of the NBA number five Johnny
Carson’s final appearance Johnny could I
have the top ten list Jay Leno may have
landed The Tonight Show gig but it was
Dave who got the last laugh when he
secured Johnny Carson’s final TV
appearance in 1994
Carson who first appeared on Letterman
in 1985 walked on stage to thunderous
applause from the audience
Letterman gave him the host chair and
for a second it seemed like Carson would
reclaim his throne he then shook his
head and as all legends do walked off
into the sunset it’s still a little warm
I wish a little that would rub off on me
Wow number four Andy Kaufman gets
slapped I don’t want to sit out here and
pretend that I’m friends with this guy
because I think he’s a wimp with Andy
Kaufman it was nearly impossible to tell
if something was real or staged Kaufman
appeared on Letterman with wrestler
Jerry Lawler who had injured Kaufman’s
neck in a wrestling match Kaufman
demanded an apology from Lawler because
of the injury while Lawler mocked
Kaufman’s neckbrace Lawler eventually
had enough and slapped Kaufman so hard
he fell out of his chair
you’re full of my friend I will
sue you for everything you have I’ll sue
your ass Kaufman unleashed a verbal
tirade on Lawler and threw a cup of
coffee at him
staged or not this is definitely one of
the more memorable moments in television
history
thanks to the studio audience we’re
putting up with this tonight I think
we’ve learned a little something about
human nature haven’t we number three
Joaquin Phoenix’s bizarre interview I
will just say right off the top here
you look different than I remember it
okay so this was a stunt performed by
Joaquin Phoenix and Casey Affleck for
the film I’m still here it’s time for me
to end this game with a brand-new star
coming to you live direct of you tear
out my spleen it’s none other than the
one and only walkie regardless this was
one of the strangest moments in the
history of Letterman’s career and it
showed just how funny but ruthless the
late-night host could be once he got his
hands on you I’ll come to your house and
chew gum to be fair Phoenix was asking
for it with his untamed hair lumberjack
beard and dark sunglasses what well can
you tell us about your days with the
Unabomber Letterman hammered Phoenix
asking him about his time with the
Unabomber and mocking his musical career
or thanks high praise coming from you he
ended the interview with the perfect
line and Joaquin I’m sorry you couldn’t
be here tonight
number two Crispin Glover nearly kicks
Dave I notice you have something there
in the case I I knew that this was gonna
happen in Phoenix may have been taking a
page out of Crispin Glover book who
appeared on Dave’s late-night show in
1987 and nearly ended up kicking
Letterman in the face you seem to make
me sound a lot weird and I’m just I’m
strong you know I’m strong I can arm
wrestle
this interview was bizarre and
uncomfortable as Glover read random
clips about himself from the newspaper
whoever was pinstripe and greased up for
the occasion
and pressing the girl things who are
trying to get next to him guess some
people are turned on by Brylcreem yeah
well perhaps more miraculous was that
Letterman allowed Glover to ramble on
incoherently okay I’m gonna go check on
the top ten until Glover almost kicked
him in the face
at which point Dave walked off the set I
would love to chat it more with Crispin
Glover but I just understand he had a
cab to catch and well
traffic this time a night here in
Midtown is pretty brutal before we
unveil our number one pick here are a
few honorable mentions for this to
happen for me to be in a comedy club and
flip out and say this crap you know I’m
I’m deeply deeply sorry while I was gone
I had quintuple bypass surgery on my
heart Oh
plus I got a haircut it isn’t where a
bad country bushes and evil lie I didn’t
say we were country I really didn’t say
he was an evil liar you’re putting words
in my mouth just the way you put
artificial facts in your head right that
was some entrance are you all right I
went to the other place and it turned
out not to be congestive heart failure
yeah no and what was the diagnosis it’s
it’s lung cancer that’s spread that’s
tough
well that means you better get your dry
cleaning done unspecial number one
drew Barrymore flashes Dave would you
like me to do dance for you wait are we
sure this was the cute innocent little
girl from et this interview started off
perfectly normal but things heated up
when Dave mentioned Drew’s recent
appearance at a club where she stripped
it’s called the Blue Angel it’s really
really cool yeah
forty-four Walker Street yeah well you
know what that’s not I know where that
is everyone including Dave was stunned
at what happens next as Barrymore jumped
onto the desk and lifted her shirt up
giving Letterman a full view I wish more
of our guests would consider that sort
of thing
Courtney Love would attempt to replicate
this act in a future interview
but it didn’t come close to reaching the
same heights as Barrymore’s Act which
Letterman still talks about to this day
it’s it’s it’s my birthday you’ve made
it amit of gasha was fun yeah that was
very nice of it it’s always a pleasure
to have here do you agree with our list
what’s your favorite David Letterman
moment what are you doing here I’m gonna
I’m doing a show I’m doing a TV show
here I thought I thought you were dead
for more great top 10s published every
day be sure to subscribe to
watchmojo.com thank you very much for
joining us tonight we’ll see you
tomorrow good night everybody
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