[Music]
okay let's all say it together awkward
oh yeah
Andy welcome to watchmojo.com omens on
late night for this list we're looking
at interviews and encounters on
late-night TV shows
we're just downright uncomfortable to
watch number 10
when Joaquin Phoenix wasn't having it
Jimmy Kimmel Live it's kind of assumed
by now for good reason that when Phoenix
does interviews things are gonna get
weird it's always his fault
who's Larry yeah
Larry is the cinematographer he's
genuinely shy and a little socially
awkward so he sometimes has trouble
following typical interview conventions
yet TV hosts keep trying we're at the
point where the awkwardness of these
encounters perhaps gives more from hosts
persisting on the other hand that is
their job Phoenix was charming while
talking about his acting but once Kimmel
became a bit more pointed and personal
Phoenix became less comfortable
defensive and less engaged private I'm
sorry about that his appearance on
Fallon during the same time also went
off the rails when the host asked a
series of personal questions in one
person remember what the first step
brothers you see Step Brothers more than
any other yeah number nine when Bill
Byrne and Sarah Silverman headed out
I Love You America with Sarah Silverman
this conversation between burne
Silverman was so cringe and confusing
that we're still not sure what happened
years later and neither is the internet
cuz every time we fight as I'm driving
home I get a text from you that says you
know I love you right
oh my go yeah I love you either these
two are very close and are just taking
the piss out of each other or this was
an impromptu therapy session exploring
their likes and dislikes for each other
I do like you and I just I've always
feel like you're frustrated with me in
honestly not knowing for sure makes it
all the more uncomfortable to be fair to
Sarah though burr is usually on the
offensive when it comes to interviews
and doesn't exude much in terms of
emotion
unless you count sarcasm and paranoia so
all things considered it could have gone
much worse right it comes from something
from your childhood or something like
that taking time bomb that your dad was
or things like that that we're out of
your control and you don't like feeling
out of control or people telling you
what to do that's my theory
emotional intervention number eight
when David Letterman and Shirley
MacLaine clashed Late Night with David
Letterman for certain celebrities
heading on to late night in the 80s was
akin to throwing raw meat into a hungry
lions cage they've mellowed out in his
later years but early on he could be
quite confrontational or as Shirley
MacLaine calls him maybe you are now
part way through this interview Dave
wanted to talk about Shirley's believe
in reincarnation but the actress didn't
think there was time to do so kept
pushing the topic MacLaine let Dave know
what she thinks of him what's truly
remarkable about the scene is the
neither guest nor host attempted to
makeup or play nice for TV hit and the
barbs just kept coming until the
interview mercifully ran out of time is
there anything else that you want to
leave us with before it's time to go
you're the interviewer you tell me you
wanted me here for three years I'm here
I think we'll probably wait another
three number-7 when Norman Mailer went
after gore Vidal the Dick Cavett show
it's hard to imagine any interview in
this day and age starting out with a
head butt backstage but that's just what
happened here Cavett's infamous
interview feature to literary
heavyweights
squaring off over their intense dislike
of one another I would apologize if if
it hurts your feelings of course I know
it hurts my sense of intellectual
pollution Mahler was a critic of the
feminist movement and Vidal took his
views to task in an essay where he
likened mailers misogyny to that of
serial killer Charles Manson perhaps
you'd like two more chairs to contain
your giant
mahler who had been drinking was furious
with rudel's article and subsequently
couldn't maintain his composure in
person head-butting and cursing the doll
backstage while openly insulting
everyone including the host and female
guests on stage talk about intense
they're here he's here I'm number 6 when
Abel Ferrara went off the rails Late
Night with Conan O'Brien if you've seen
Ferrara's 1992 film Bad Lieutenant you
would know that the director is not
afraid of controversy which Conan
acknowledged while inviting him onstage
at his old show about the Conan there
you go alright cool you just passed
their sobriety test here alright so not
surprisingly controversy is exactly what
ensued Ferrara was accused of showing up
drunk refusing to go onstage and at one
point even leaving the NBC studio
requiring staff members to track him
down I want to talk about are behind you
say I want to talk about Harvey Keitel
go ahead if you thought that sounds like
a mess just watch the interview Ferrara
is barely audible at times slurring and
rambling and coherently to the point
where conan suggests viewers will need
subtitles to understand him conan later
admitted that in his entire career Abel
Ferrara was by far the absolutely worst
guest he's ever interviewed number five
when Jimmy Kimmel mocked Jay Leno to his
face the Jay Leno Show
remember the Late Night Wars and this is
for kids at home if you have silly putty
to make yourself a nice big Dudley
do-right chin that works
well Jimmy Kimmel sure how to take and
he didn't take kindly to Jay Leno's
actions ruthlessly mocking and
impersonating Jay during Leno's
drawn-out Tonight Show dust-up with
Conan O'Brien I don't think people care
about what I have to say I agree with
that tomorrow night I act my nights bad
for me all right let's move on for some
odd reason Leno's producers then thought
it would be a good idea to have Kimmel
on Jays new show and well it plays out
exactly as you would expect
Leno clearly hates camels impression of
him and Jimmy takes every opportunity to
insult Jay on his own show but the best
I think the best prank I ever pulled was
I told the guy I told the guy that five
years from now I'm gonna give you my
show and then when the five years came I
gave it to him and then I took it back
almost a mile away watching Leno forcing
himself to laugh while Jimmy drops bombs
on him is the equivalent of having a
smile while being punched in the face
number four when David Letterman
shredded Paris Hilton Late Show with
David Letterman woman of many talents
she is a film star a recording artist
and an entrepreneur it took Letterman
about a fraction of a second to insult
Hilton when she unwisely appeared on a
show in 2007 after serving time in jail
they've introduced her as quote a woman
of many talents with a sharp grin on his
face and then went straight to pressing
and mocking Paris on her jail stay have
your friends treated you differently
since you've been out of the slammer
Hilton initially put on a brave face but
soon refused to talk about her time in
the clink while shooting Dave some dirty
looks this is so painful to watch
because she is drastically outmatched
here and obviously cannot trade in
sarcasm and insults with a master like
Letterman in fact it's just unfair at
some points and we kind of wish there
were a referee present to stop the fight
you're making me sad that I came because
no please don't don't be said are you
really said no are you feeling better
now number three when Jennifer Garner
got schooled Late Night with Conan
O'Brien
Conan went to Harvard and while that
doesn't always mean anything he is
clearly a sharp guy
there's a time when you snuck into the
room to see what the pitch into the room
snuck isn't a word Conan and you went to
Harvard and you should know that so
Jennifer Garner probably shouldn't have
called out O'Brien for his ultimately
correct language usage before mocking
his education and one of the best
universities in the world but she did
luckily it was all in good fun but being
the nerd he is Conan couldn't let the
opportunity pass to whip out a
dictionary and school Garner quite
literally I keep a dictionary down here
and I just found it I just want to look
at what the hell look right here
snuck past and passed part of Jennifer
goes from confidently and
enthusiastically talking about her
latest role to utter silence and with
more than a hint of embarrassment as
professor O'Brien rubs it in number two
when Madonna let loose Late Show with
David Letterman just like you never know
how a Letterman interview will go you
never know how a Madonna guest
appearance will turn out
I gave him my underpants but we know one
thing for sure everyone at the FCC was
having a collective heart attack during
this profanity written innuendo driven a
filthily funny interview oh where to
begin really countless f-bombs and
anatomy jokes are one thing but it's
Madonna's constant insistence that
Dave's obsessed with her sexually and
while never denying this claim Dave's
flirty behavior that really make this
one for the agents you can't get through
a show without talking about a minute or
thinking about do they like each other
do they loathe each other just what are
we watching here it feels like either a
fight or a snog fest is about to break
out and both outcomes are equally
worrisome I get a big kick out of you
and I mean wait we're just you know out
of your body yeah I think you're a
nightmare you know I think you're a
decent nice person you know uh-huh all I
can say about this list is me and our
number one is a pop-culture moment
everyone was talking about in 2009 and
while we've since gotten an explanation
about what was going on it's no less
awkward to watch today
so let's suffer through the cringe
factor of our honorable
mentions and then we'll see the most
Awkward late-night moment is there
anybody you'd like to apologize to right
now yourself no I'm strong you know I'm
strong I can arm wrestle I love do you
wanna arm at heart line I can I can kick
okay hey I'm gonna go check on the top
ten and I said you've been on the show
like five hundred times do they have
like a cake for you once a year or
something I'm not funny huh yes you are
what you do is you try to maximize and
you honestly believe in respective here
I don't care irrespective irrespective
of what the Osher helpers
we're really friends I think we ate at
Planet Hollywood I think we're just
anything desperately thirstily trying to
get attention now you go
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number one when Joaquin Phoenix seemed
nutty Late Show with David Letterman wow
Akeem again sure his whole shtick turned
out to be a whacky piece of performance
art for a mockumentary that he and Casey
Affleck were making but in 2009 the
world collectively thought that Joaquin
had fully lost his mind there's nothing
wrong I can't be the first one to make
you feel weird he claimed he was
transitioning to a career in hip hop yet
he could barely string two sentences
together in real time I do
hip hop music was he drunk hi sick dying
for every time someone asked one of
these questions the outcome was a
torrent of opinion pieces and endless
speculation that filled the internet for
months yet the one thing we did not get
for over a year and a half was answers
Joaquin returned to Late Show in 2010
and apologized for his behavior
but even that interview was a little
awkward but I apologize I didn't I hope
I didn't offend you I was not offended
okay I'm telling you it was so much fun
it really it was good do you agree with
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[Music]
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