A Legacy Of Laughs: Highlighting Our Favorite Sketches From ‘Chappelle’s Show’

Source:
Jason
Mendez
/
Getty

One
of
the
funniest
shows
we’ve
ever
seen
premiered
21
years
ago
today
(January
22).
Click
inside
to
check
out
some
of
the
best
sketches
from
the
groundbreaking
series!

Dave
Chappelle
is
and
will
always
be
a
household
name
in
comedy.
The
Washington,
D.C.
native
got
his
start
studying
theater
arts
at
the
Duke
ellington
School
of
the
Arts,
where
he
graduated
in
1991.
Upon
graduating,
he
moved
to
New
York
City
to
pursue
his
comedy
career.
Chappelle
has
often
noted
that
being
booed
off
stage
while
performing
at
Harlem
Apollo
Theater’s
“Amateur
Night”
gave
him
the
courage
to
continue
his
show
business
aspirations.

It’s
a
good
thing
that
he
kept
going.
In
1992,
Chappelle
started
to
gain
critical
and
popular
acclaim
for
his
performance
on
Russell
Simmons’

Def
Comedy
Jam on HBO.
His
popularity
began
to
grow
so
much
that
he
became
a
regular
on
late-night
television
shows
(including
David
Letterman,
Howard
Stern
and
Conan
O’Brien).
Over
the
next
couple
of
years,
he
continued
working
on
his
stand-up
career
while
also
appearing
in
films
and
sitcoms.
He
got
his
biggest
break
to
date
in
1996
when
he
appeared
in The
Nutty
Professor. Two
years
later,
he
and
Neal
Brennan
co-wrote
the
1998
stoner
comedy Half
Baked
(in
which
Chappelle
also
starred).
In
2000,
Chappelle
recorded
his
first
hour-long
HBO
special Dave
Chappelle:
Killin’
Them
Softly. He
appeared
in Undercover
Brother in
2002
before
turning
his
focus
to
the
show
that
would
launch
him
into
unquestioned
superstardom.

After
reuniting
with
co-creator
Neal
Brennan,
Chappelle
debuted
his
weekly
sketch
comedy
show
on
Comedy
Central
called Chappelle’s
Show in
2003.
The
show
parodied
many
aspects
of
American
culture,
including racial
stereotypes,
politics
and pop
culture.
The
show
also
featured
musical
performances
from
various
hip-hop
and
soul
artists.
The
show’s
popularity
skyrocketed
to
new
heights
so
much
that
Comedy
Central’s
parent
company
Viacom
offered
Chappelle
a
$55
million
(Dave
would
get
a
share
of
DVD
sales)
contract
to continue
production
of Chappelle’s
Show
for
two
more
years
while
allowing
him
to
do
side
projects.
Unfortunately,
Chappelle
started
to
become
frustrated
with
the
direction
the
show
was
going
(and
the
entertainment
industry’s
tone
deaf-ness
to
Black
entertainers
and
viewers)
and
ended
up
walking
away
from
it
all.

Although
the
show
coming
to
an
end
was
sad
for
a
lot
of
people,
the
laughter
and
iconic
moments Chappelle’s
Show gave
viewers
will
never
be
forgotten
or
duplicated.
To
celebrate
its
legacy,
check
out
a
gallery
of
the
best
sketches
from
the
legendary
show.Slide
in
the
comments
and
let
us
know
which
ones
are
your
favorites
and
if
you
think
we
forgot
any!