Dave Chappelle’s comedy is a hell of a
drug welcome to watchmojo.com and today
we’re counting down our picks for the
top 10 Dave Chappelle moments before we
begin we publish new videos every day so
be sure to subscribe for more great
content for this list we’re looking at
his most memorable and funny sketches
interviews and movie roles number 10
where’s jaw Dave Chappelle for what it’s
worth celebrity culture is ubiquitous
and has been for decades now but what
really rankled Dave – hilarious effect
was the tendency for news organizations
to ask famous people to weigh in on
heavy topics that were way out of their
depth so in this short bit Dave
admonishes the press for inflating the
already large ego of celebrities to
illustrate his point he chose rapper Ja
Rule interviewed on MTV about the
September 11th terrorist attacks like
much of Chappelle standup
this jab at pop culture found a new life
of its own on the Internet number 9
conspiracy brother undercover brother in
the blaxploitation spoof film Undercover
Brother Dave plays a conspiracy driven
agent named you guessed it conspiracy
brother know that beast
bowling from the black man tracking down
appropriations of black culture is a
specialty and he spends much of his
efforts making sure that all the other
characters know all the conspiracies
that he can make them aware of
[Music]
conspiracy brother is part of the
Brotherhood a secret agency that puts
its efforts into taking down the agenda
of the man though he rants and raves a
lot in this movie it wouldn’t be a
Chappelle character if there wasn’t some
weed involved just be careful with this
because he smoked too much it’s gonna
have y’all paranoid and shit takes a
while to build up a tolerance take
number eight a moment in the life of Lil
Jon Chappelle’s Show
the early 2000s saw the rise of crunk
music hint its leader went by the name
of Lil Jon in addition to deep thumping
booty shaking rhythms well jon is known
for his full-throated strange utterances
like yeah and okay throughout his songs
this got taken to a new level when Dave
spoofed Lil Jon and this skit on the
seminal Chappelle’s Show fractured your
arm besides becoming one of the most
popular of Dave skits it also shot
little Jon to even greater heights of
Fame you have your proof of insurance
yet he still claims that he can’t walk
down the street without some fan running
up and screaming yeah right in his face
[Music]
[Applause]
mr. Jolin you’re all set number seven
revealing interview The Oprah Winfrey
Show what would you do if you got
offered tens of millions of dollars to
continue a super popular sketch comedy
show well if you’re Dave Chappelle you
quit leave for Africa and spark rumors
that you have literally gone crazy by
the time he made it onto Oprah’s famous
couch in 2006 fans were on edge to hear
if they would ever see their beloved
Chappelle’s Show again and find out the
truth about all the seemingly strange
behavior generates money yeah people
have a vested interest in controlling
the queen of daytime talk was the only
person that he would interview with at
the time and he spent the hour walking
through the highs and lows that got him
to a point of no return I know the
difference of people laughing with me
and people laughing at me and was the
first time I’ve ever got a laugh that I
was uncomfortable with but like number
six return to form deep in the heart of
Texas and the age of spin after some
time away from TV Dave Chappelle
culminated his return to fame with a
vengeance in 2017 with two stand-up
comedy specials released by Netflix they
of course garnered a hot buzz before
their release and Netflix has stated
that the specials became the most viewed
programs on the streaming service ever
Dave’s ease with the audience and
effortless storytelling a reminiscent of
the glory of Chappelle’s Show monologues
and please walk up to the window mr.
Chappelle
we had to arrest your friend he refused
to take our breathalyzer test doesn’t
love it but Netflix wasn’t the only
winner Dave reportedly took home 60
million dollars haiya
number five Thurgood Ekans sir smoke a
lot half-baked this doner cult classic
which he also co-wrote was one of Dave’s
first starring roles the 1998 film
brought together Chappelle and writer
slash comedian Neal Brennan who would
together go on to co-create Chappelle’s
Show
the film is no stranger to controversy
with the opening scene almost yanked by
the studio because it showed kids
smoking marijuana another great reason
to love this movie are all the cameo
appearances from other comics like Tracy
Morgan Janeane Garofalo Jon Stewart and
Bob Saget meanwhile Chappelle had to
show off his acting chops both as
protagonist durga jenkins and sir smoke
a lot for the ni GGA our family
Chappelle’s Show this famous skit is a
spoof of a 1960s Andy Griffith style
sitcom that stars a family with an
unfortunate last name wrapped in this
uncomfortable sequence is the social
question of the use of the n-word and
the effect that it would have if it were
just another name jenny has a date
tonight his name Timmy for some viewers
it raised questions about racial versus
racist humor and it certainly pushed the
limits of what you could get away with
on television for others it was a damn
funny skit that proved that we were all
taking things a bit too seriously
three men and women Dave Chappelle
killing them softly this bit comes from
Dave’s killing them softly special a fan
favorite performed at the Lincoln
Theater in Washington DC in 2000
chivalry is dead and women killed it
this stand-up set is seen as a turning
point in Dave’s career pointing him
towards superstardom men have nice cars
not because they like nice cars because
they know women like nice car
although Dave is known for his racial
humor this skit is a departure instead
focusing on the craziness between men
and women and the things that people go
through to have relationships
the page you turn you start feeling
fatter and uglier and you feel like your
clothes aren’t good enough and the
magazines have you forgettin how
beautiful you are and that’s what
happened look what happens
this was another look at cool calm and
collected Dave on stage and easily
working an audience number two election
night skit Saturday Night Live
election night 2016 was quite the
emotional roller coaster in the u.s. at
a time when the country was riven by
partisanship and anger Dave was one of
the first to get people to laugh at an
intense situation we’re about to have
our first woman president like this is
gonna be a story night this election
night skit highlights the surprise and
dismay of Hillary supporters who weren’t
anticipating Donald Trump’s win oh my
god I think America is racist oh my god
as the night goes on more and more
states are called for Trump and the
election night gathering turns from
happiness to disbelief to depression
plus bonus surprise guest Chris Rock God
this is the most shameful thing America
has ever done before we unveil our
number-one pick here are some honorable
mentions
[Music]
[Applause]
this is the way the dialogue Suites you
trying to get some of this hot fire
tastes like athlete’s foot I feel sick
but I’m not really hot then I looked in
the mirror
number one Rick James Chappelle’s Show
[Music]
yes it’s this skit bitch
Chappelle’s hilarious outsize turn as
the couch disrespecting funk legend Rick
James earth catchphrases and memes
galore the skit part of cast mate
Charlie Murphy’s true Hollywood story
segment also included the real Rick
James bustin out his classic line pun
intended about drug use cocaine is a
hell of a drug the quote ability of the
skit made it prime shareable and viral
content for the burgeoning internet hype
machine and while Rick James passed in
2004 and Charlie Murphy in 2017 this bit
of peak Chappelle remains forever
alive do you agree with our picks check
out these other great clips from
WatchMojo and subscribe for new videos
every day
drug welcome to watchmojo.com and today
we’re counting down our picks for the
top 10 Dave Chappelle moments before we
begin we publish new videos every day so
be sure to subscribe for more great
content for this list we’re looking at
his most memorable and funny sketches
interviews and movie roles number 10
where’s jaw Dave Chappelle for what it’s
worth celebrity culture is ubiquitous
and has been for decades now but what
really rankled Dave – hilarious effect
was the tendency for news organizations
to ask famous people to weigh in on
heavy topics that were way out of their
depth so in this short bit Dave
admonishes the press for inflating the
already large ego of celebrities to
illustrate his point he chose rapper Ja
Rule interviewed on MTV about the
September 11th terrorist attacks like
much of Chappelle standup
this jab at pop culture found a new life
of its own on the Internet number 9
conspiracy brother undercover brother in
the blaxploitation spoof film Undercover
Brother Dave plays a conspiracy driven
agent named you guessed it conspiracy
brother know that beast
bowling from the black man tracking down
appropriations of black culture is a
specialty and he spends much of his
efforts making sure that all the other
characters know all the conspiracies
that he can make them aware of
[Music]
conspiracy brother is part of the
Brotherhood a secret agency that puts
its efforts into taking down the agenda
of the man though he rants and raves a
lot in this movie it wouldn’t be a
Chappelle character if there wasn’t some
weed involved just be careful with this
because he smoked too much it’s gonna
have y’all paranoid and shit takes a
while to build up a tolerance take
number eight a moment in the life of Lil
Jon Chappelle’s Show
the early 2000s saw the rise of crunk
music hint its leader went by the name
of Lil Jon in addition to deep thumping
booty shaking rhythms well jon is known
for his full-throated strange utterances
like yeah and okay throughout his songs
this got taken to a new level when Dave
spoofed Lil Jon and this skit on the
seminal Chappelle’s Show fractured your
arm besides becoming one of the most
popular of Dave skits it also shot
little Jon to even greater heights of
Fame you have your proof of insurance
yet he still claims that he can’t walk
down the street without some fan running
up and screaming yeah right in his face
[Music]
[Applause]
mr. Jolin you’re all set number seven
revealing interview The Oprah Winfrey
Show what would you do if you got
offered tens of millions of dollars to
continue a super popular sketch comedy
show well if you’re Dave Chappelle you
quit leave for Africa and spark rumors
that you have literally gone crazy by
the time he made it onto Oprah’s famous
couch in 2006 fans were on edge to hear
if they would ever see their beloved
Chappelle’s Show again and find out the
truth about all the seemingly strange
behavior generates money yeah people
have a vested interest in controlling
the queen of daytime talk was the only
person that he would interview with at
the time and he spent the hour walking
through the highs and lows that got him
to a point of no return I know the
difference of people laughing with me
and people laughing at me and was the
first time I’ve ever got a laugh that I
was uncomfortable with but like number
six return to form deep in the heart of
Texas and the age of spin after some
time away from TV Dave Chappelle
culminated his return to fame with a
vengeance in 2017 with two stand-up
comedy specials released by Netflix they
of course garnered a hot buzz before
their release and Netflix has stated
that the specials became the most viewed
programs on the streaming service ever
Dave’s ease with the audience and
effortless storytelling a reminiscent of
the glory of Chappelle’s Show monologues
and please walk up to the window mr.
Chappelle
we had to arrest your friend he refused
to take our breathalyzer test doesn’t
love it but Netflix wasn’t the only
winner Dave reportedly took home 60
million dollars haiya
number five Thurgood Ekans sir smoke a
lot half-baked this doner cult classic
which he also co-wrote was one of Dave’s
first starring roles the 1998 film
brought together Chappelle and writer
slash comedian Neal Brennan who would
together go on to co-create Chappelle’s
Show
the film is no stranger to controversy
with the opening scene almost yanked by
the studio because it showed kids
smoking marijuana another great reason
to love this movie are all the cameo
appearances from other comics like Tracy
Morgan Janeane Garofalo Jon Stewart and
Bob Saget meanwhile Chappelle had to
show off his acting chops both as
protagonist durga jenkins and sir smoke
a lot for the ni GGA our family
Chappelle’s Show this famous skit is a
spoof of a 1960s Andy Griffith style
sitcom that stars a family with an
unfortunate last name wrapped in this
uncomfortable sequence is the social
question of the use of the n-word and
the effect that it would have if it were
just another name jenny has a date
tonight his name Timmy for some viewers
it raised questions about racial versus
racist humor and it certainly pushed the
limits of what you could get away with
on television for others it was a damn
funny skit that proved that we were all
taking things a bit too seriously
three men and women Dave Chappelle
killing them softly this bit comes from
Dave’s killing them softly special a fan
favorite performed at the Lincoln
Theater in Washington DC in 2000
chivalry is dead and women killed it
this stand-up set is seen as a turning
point in Dave’s career pointing him
towards superstardom men have nice cars
not because they like nice cars because
they know women like nice car
although Dave is known for his racial
humor this skit is a departure instead
focusing on the craziness between men
and women and the things that people go
through to have relationships
the page you turn you start feeling
fatter and uglier and you feel like your
clothes aren’t good enough and the
magazines have you forgettin how
beautiful you are and that’s what
happened look what happens
this was another look at cool calm and
collected Dave on stage and easily
working an audience number two election
night skit Saturday Night Live
election night 2016 was quite the
emotional roller coaster in the u.s. at
a time when the country was riven by
partisanship and anger Dave was one of
the first to get people to laugh at an
intense situation we’re about to have
our first woman president like this is
gonna be a story night this election
night skit highlights the surprise and
dismay of Hillary supporters who weren’t
anticipating Donald Trump’s win oh my
god I think America is racist oh my god
as the night goes on more and more
states are called for Trump and the
election night gathering turns from
happiness to disbelief to depression
plus bonus surprise guest Chris Rock God
this is the most shameful thing America
has ever done before we unveil our
number-one pick here are some honorable
mentions
[Music]
[Applause]
this is the way the dialogue Suites you
trying to get some of this hot fire
tastes like athlete’s foot I feel sick
but I’m not really hot then I looked in
the mirror
number one Rick James Chappelle’s Show
[Music]
yes it’s this skit bitch
Chappelle’s hilarious outsize turn as
the couch disrespecting funk legend Rick
James earth catchphrases and memes
galore the skit part of cast mate
Charlie Murphy’s true Hollywood story
segment also included the real Rick
James bustin out his classic line pun
intended about drug use cocaine is a
hell of a drug the quote ability of the
skit made it prime shareable and viral
content for the burgeoning internet hype
machine and while Rick James passed in
2004 and Charlie Murphy in 2017 this bit
of peak Chappelle remains forever
alive do you agree with our picks check
out these other great clips from
WatchMojo and subscribe for new videos
every day
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