in many regards David Letterman is the
perfect antidote to the airless
celebrity interview during his long
legendary tenure as a late-night
talk-show host he earned a reputation
for keeping guests on their toes and
cracking plenty of jokes at their
expense of course Letterman has also
fallen victim to plenty of guests who
went out their way to be openly
confrontational provocative and
gleefully obnoxious here's a closer look
at some of David Letterman's most
uncomfortable interviews Madonna People
magazine called Madonna's March 1994
appearance on The Late Show the most
censored Network talk show episode in
history it finds the popstar at her most
experimentally insufferable to be fair
Letterman wasn't exactly in fine form
either yes tonight is one of the biggest
stars in the world in the past ten years
she has sold over 80 million albums
starred in countless films and slept
with some of the biggest names in the
entertainment Madonna took the stage she
handed Letterman a bulldog pair of
underwear
she also chomped and sucked on a cigar
said the f-word 14 times and compared a
microphone to a particular part of the
male anatomy she also refused to leave
the stage prompting aggravated folks in
the audience to shout no no that's the
guy you wouldn't kiss earlier after a
commercial break Letterman dropped this
singer well I see we've been canceled
there is no show tomorrow night Justin
Bieber
it would seem David Letterman is not a
fan of body art nor is he particularly
fond of Justin Bieber when the Biebs
breezed onto the Late Show in June 2012
the comedian Lee host gave him
considerable grief for some new ink
things went from merely uncomfortable to
all-out intense when Letterman grabbed
hold of Bieber's arm and started
meddling with the singers new believe
tattoo you know I got believed
this is a brand-new the awkwardness
didn't end there as Letterman advised
Bieber not to completely cover himself
in tattoos like the Sistine Chapel
- which bieber responded by going for
the 16th chapel canadian high school
michael richards talked about a
switcheroo anyone who tuned in to watch
Jerry Seinfeld's interview with
Letterman in November 2006 was instead
treated to a blazingly awkward apology
from Michael Richards who appeared by a
satellite from Los Angeles Richards had
recently spewed out a litany of racist
slurs during a stand-up comedy routine
during his Late Show apology he used
some awkward terminology nasty things to
some afro-americans about a trash talk
and laughing a dazed glassy-eyed riches
wasn't even sure this was the best way
to address the situation but he made an
effort to salvage the moment I just have
to do personal work Crispin Glover in
July 1987 actor Crispin Glover appeared
on Late Night and kicked up in a
free-floating anxiety to blow a hole
through the space-time continuum from
the moment Glover sauntered on stage in
a bizarro fright wig tight pinstripe
slacks platform shoes and cooked out
glasses it was clear this interview was
being transmitted from the dark side of
the crystal in a singsong voice Glover
read excerpts from an LA Weekly article
that disparaged him prompting Letterman
to ask his sidekick Paul Shaffer this
the first time you've seen another guy
drowned
this is the first time you've watched a
guide I know me the situation escalated
when Glover challenged Letterman to an
impromptu armwrestling match and then
unleashed a karate kick that almost hit
Letterman in the face I'm gonna go check
on the top ten
galava has remained tight-lipped about
what prompted his dazzling tour-de-force
freak-outs though he offered a bit of an
explanation in a follow-up appearance a
few weeks later I'll say it was you know
I was kind of I wanted it to be this
interesting kind of a thing that would
happen that people would find
interesting Andy Kaufman legendary comic
Andy Kaufman stopped by Late Night with
David Letterman on several occasions and
every appearance was pretty
uncomfortable in one way or another but
the most uncomfortable of them all was
probably the 1982 episode in which he
got knocked right out of his chair by
wrestler Jerry Lawler at the time the
comedian was referring to himself as the
world's first into gender wrestling
champion the scuffle was big news but in
truth there was never any real animosity
between Kaufman and Lawler who told film
fad in 2014 that the moment was just
almost like improv
Oh
Joaquin Phoenix in February 2009
Joaquin Phoenix put his own awkward spin
on Andy Kaufman's prankish performance
art during his interview with Letterman
the usually clean-cut actor looked like
a cross between a hobo a cult leader and
a late career Jim Morrison what what can
you tell us about your days with the
Unabomber it turned out that the dazed
and mumbly appearance was part of a
lengthy publicity campaign for the
mockumentary I'm still here which
imagined Phoenix abandoning acting to
pursue a new career as a hip hop artist
and Joaquin I'm sorry you couldn't be
here tonight
phone
[Music]