some were lovable some were laughable
and some were downright unrecognizable
experi can be welcome to watchmojo.com
and today we’re counting down our picks
for the top 10 cross-dressing roles for
this list we’ve decided to stay away
from more serious cross-dressing roles
and have instead focused on more comedic
films that made us laugh giggle and
sometimes cringe yeah well maybe my
balls don’t itch all balls itch it’s a
fact number 10
Joyce Heiser as Terry Griffith just one
of the guys sometimes I just wish I were
a guy in this enjoyable 80s romp Heiser
plays a teenage girl on a mission to
prove her skills as a journalist by
dressing as a teenage boy I’m gonna take
that article to Sturgis water and I’m
gonna submit it as a guy turned down for
an internship supposedly due to her good
looks she’s out to demonstrate that
she’s more than just a pretty face I
write an excellent article and just
because I’m cute no one takes me
seriously she makes a convincing teenage
boy and teenage girl making her
performance fairly spot-on wait a minute
are those what I think they are sorry
where do you get off having pits number
9 Johnny Depp as Edie would edwood heart
do you think you’re doing
under acting as a self-proclaimed
transvestite Edie would enjoyed the
occasional poodle skirt and heels combo
alright everybody let’s get set up for
scene 112 Johnny Depp’s turn as the cult
film director offered up the perfect
amount of pep perkiness and pleasant
disposition adding humor and the
occasional dash of gravitas to the role
I like to dress in women’s clothing
the film garnered rave reviews and even
though it’s not a huge plot point we
think Depp’s cross-dressing performance
helped it along
how can you casual when you’re dressed
like that it makes me feel comfortable
number 8 Shawn and Marlon Wayans as the
Wilson sisters white chicks the Wayans
brothers play two FBI detectives who go
undercover as a couple of socialites
sisters in this extreme case of
cross-dressing gone wild no hopping home
a Pune Hale what’s up yeah got problem
the brothers transformation into the
pair of white chicks is completed with
full body makeup contact lenses nasal
prosthetics and wigs it’s pretty
convincing in a creepy uncomfortable
pseudo racist kind of way
take them away downtown walking fast
Oh
number seven Martin Lawrence as Big Mama
Big Momma’s House look at you Big Mama
hardly recognize you
Janice only makeup that in this gender
swapping film Martin Lawrence plays
Malcolm Turner yet another FBI agent who
must go undercover as a woman to unravel
a criminal scheme then she’s just gonna
leave and then we have no case
worry Big Mama be here
Lawrence Don’s a fat suit and undergoes
hours of makeup to be turned into Big
Mama
a southern matriarch and the key to
cracking the bank robbery case
shenanigans ensue and Lawrence
eventually ends up solving the crime and
winning the girl at the end cuz it’s
what’s on the inside that counts
boo mama yeah is there another
flashlight over there
number six Nathan Lane as mrs. Coleman
The Birdcage oh yes Coleman the D is
silent in America Lane actually plays
Albert one-half of a gay couple who goes
all out to impress a conservative
straight-laced family well she told him
that you were the cultural attache to
Greece and Albert was a housewife what
Albert takes on the role of mrs. Coleman
a traditional wife and mother who must
convince the parents of his boyfriend’s
son’s fiancee that he and his partner
are a conventional right-wing American
family maybe I’m just an old-fashioned
girl but I pity the woman who’s too busy
to stay home and take care of a man of
course there’s lots of confusion but
Lane’s performance as a middle-aged
married woman is a standout moment in
the film
number five Patrick Swayze Wesley Snipes
and John Leguizamo as drag queens to
Wong foo thanks for everything Julie
Newmar darling if you’re going to become
a drag queen you’re gonna have to learn
this thing these three men deviate
entirely from their ultra macho action
hero personas with their performance as
three drag queens stranded in a small
town well ladies welcome to snydersville
thank you headed to a drag show pageant
when their car breaks down vida boheme
noxeema jackson and chi Chi Rodriguez
inject a little fabulousness into the
town before taking off in a trail of
glitter and fierceness we may have
cringed a fair amount but these
performances are undeniably entertaining
I’m just a sweet transvestite number
four Tim Curry as dr. Franken furder the
Rocky Horror Picture Show
curry plays this sweet transvestite in
his role in the 1970s cult classic
wearing tons of makeup heels and garters
curry struts and performs the iconic
character that garnered a cult following
unparalleled in movie history it’s just
a jump to the left his performance as
the swings both ways doctor is memorable
not just because of the lipstick but
also for his mischievous and
entertaining delivery it’s not easy
having a good time
number three Tony Curtis and Jack Lemmon
as Josephine and Daphne some like it hot
but you’re not a girl you’re a guy and
why would a guy want to marry a guy
security Kurtis and lemon pair up in
this classic comedy as a couple of jazz
musicians hiding out from the mob it’s
no use we’re not gonna get away with
each other name is Josephine in this
withdraw right in a first place after
witnessing the infamous st. Valentine’s
Day Massacre the two decide it would be
prudent to dress up as ladies and hit
the road with an all-female band we have
been playing with the wrong band John
Daphne maintaining the farce becomes
difficult however when they encountered
the sultry and irresistible miss sugar
cane does have anything I can do for you
I can think of a million things number
two Robin Williams as mrs. euphegenia
doubtfire
mrs. Doubtfire Williams plays an
unemployed actor and devoted father who
will do anything to spend more time with
his kids he’ll even wear a dress and get
a job as their nanny Oh
nigger this my first day as a woman
getting hot flashes his makeover is so
thorough not even his own children
recognize him and eventually he wins
their hearts as their strict yet lovable
caregiver mrs. Doubtfire not anymore the
only thing you’ll be watching is deep CN
n by the end of the movie he’s found out
but finds a less strange way to see his
kids
before we unveil our number one pick
here are a few honorable mentions that
woman is a woman a woman
you mean that good I must be absolutely
crazy how did I ever let it get this far
I don’t call me that
can’t help it a girl has a feeling thing
is deal you’re not a girl
details baby details I mean sorry you
have to see that but you know how it is
when you get those are manly urges huh
my name is Dorothy number one Dustin
Hoffman is Dorothy Michaels Tootsie
Michael Dorsey can’t land an acting job
for the life of him so he takes matters
into his own hands and decides to try
his luck as a woman you’re not
threatening and I’m threatening enough
how’s this you take your hands off me
Roman I need your balls right through
the roof your mass these efforts are
complicated by the relationships with
the women in his life the suitors
interested in his new persona and his
sudden jump into stardom
disqualified Hoffman’s role as Dorothy
Michaels was so spot-on it led to an
Oscar nomination
that means you dear Miss Marshall shame
on you you macho shithead do you agree
with our list what’s your favorite
cross-dressing role for more
entertaining top 10s published daily be
sure to subscribe to watchmojo.com what
are you looking at
and some were downright unrecognizable
experi can be welcome to watchmojo.com
and today we’re counting down our picks
for the top 10 cross-dressing roles for
this list we’ve decided to stay away
from more serious cross-dressing roles
and have instead focused on more comedic
films that made us laugh giggle and
sometimes cringe yeah well maybe my
balls don’t itch all balls itch it’s a
fact number 10
Joyce Heiser as Terry Griffith just one
of the guys sometimes I just wish I were
a guy in this enjoyable 80s romp Heiser
plays a teenage girl on a mission to
prove her skills as a journalist by
dressing as a teenage boy I’m gonna take
that article to Sturgis water and I’m
gonna submit it as a guy turned down for
an internship supposedly due to her good
looks she’s out to demonstrate that
she’s more than just a pretty face I
write an excellent article and just
because I’m cute no one takes me
seriously she makes a convincing teenage
boy and teenage girl making her
performance fairly spot-on wait a minute
are those what I think they are sorry
where do you get off having pits number
9 Johnny Depp as Edie would edwood heart
do you think you’re doing
under acting as a self-proclaimed
transvestite Edie would enjoyed the
occasional poodle skirt and heels combo
alright everybody let’s get set up for
scene 112 Johnny Depp’s turn as the cult
film director offered up the perfect
amount of pep perkiness and pleasant
disposition adding humor and the
occasional dash of gravitas to the role
I like to dress in women’s clothing
the film garnered rave reviews and even
though it’s not a huge plot point we
think Depp’s cross-dressing performance
helped it along
how can you casual when you’re dressed
like that it makes me feel comfortable
number 8 Shawn and Marlon Wayans as the
Wilson sisters white chicks the Wayans
brothers play two FBI detectives who go
undercover as a couple of socialites
sisters in this extreme case of
cross-dressing gone wild no hopping home
a Pune Hale what’s up yeah got problem
the brothers transformation into the
pair of white chicks is completed with
full body makeup contact lenses nasal
prosthetics and wigs it’s pretty
convincing in a creepy uncomfortable
pseudo racist kind of way
take them away downtown walking fast
Oh
number seven Martin Lawrence as Big Mama
Big Momma’s House look at you Big Mama
hardly recognize you
Janice only makeup that in this gender
swapping film Martin Lawrence plays
Malcolm Turner yet another FBI agent who
must go undercover as a woman to unravel
a criminal scheme then she’s just gonna
leave and then we have no case
worry Big Mama be here
Lawrence Don’s a fat suit and undergoes
hours of makeup to be turned into Big
Mama
a southern matriarch and the key to
cracking the bank robbery case
shenanigans ensue and Lawrence
eventually ends up solving the crime and
winning the girl at the end cuz it’s
what’s on the inside that counts
boo mama yeah is there another
flashlight over there
number six Nathan Lane as mrs. Coleman
The Birdcage oh yes Coleman the D is
silent in America Lane actually plays
Albert one-half of a gay couple who goes
all out to impress a conservative
straight-laced family well she told him
that you were the cultural attache to
Greece and Albert was a housewife what
Albert takes on the role of mrs. Coleman
a traditional wife and mother who must
convince the parents of his boyfriend’s
son’s fiancee that he and his partner
are a conventional right-wing American
family maybe I’m just an old-fashioned
girl but I pity the woman who’s too busy
to stay home and take care of a man of
course there’s lots of confusion but
Lane’s performance as a middle-aged
married woman is a standout moment in
the film
number five Patrick Swayze Wesley Snipes
and John Leguizamo as drag queens to
Wong foo thanks for everything Julie
Newmar darling if you’re going to become
a drag queen you’re gonna have to learn
this thing these three men deviate
entirely from their ultra macho action
hero personas with their performance as
three drag queens stranded in a small
town well ladies welcome to snydersville
thank you headed to a drag show pageant
when their car breaks down vida boheme
noxeema jackson and chi Chi Rodriguez
inject a little fabulousness into the
town before taking off in a trail of
glitter and fierceness we may have
cringed a fair amount but these
performances are undeniably entertaining
I’m just a sweet transvestite number
four Tim Curry as dr. Franken furder the
Rocky Horror Picture Show
curry plays this sweet transvestite in
his role in the 1970s cult classic
wearing tons of makeup heels and garters
curry struts and performs the iconic
character that garnered a cult following
unparalleled in movie history it’s just
a jump to the left his performance as
the swings both ways doctor is memorable
not just because of the lipstick but
also for his mischievous and
entertaining delivery it’s not easy
having a good time
number three Tony Curtis and Jack Lemmon
as Josephine and Daphne some like it hot
but you’re not a girl you’re a guy and
why would a guy want to marry a guy
security Kurtis and lemon pair up in
this classic comedy as a couple of jazz
musicians hiding out from the mob it’s
no use we’re not gonna get away with
each other name is Josephine in this
withdraw right in a first place after
witnessing the infamous st. Valentine’s
Day Massacre the two decide it would be
prudent to dress up as ladies and hit
the road with an all-female band we have
been playing with the wrong band John
Daphne maintaining the farce becomes
difficult however when they encountered
the sultry and irresistible miss sugar
cane does have anything I can do for you
I can think of a million things number
two Robin Williams as mrs. euphegenia
doubtfire
mrs. Doubtfire Williams plays an
unemployed actor and devoted father who
will do anything to spend more time with
his kids he’ll even wear a dress and get
a job as their nanny Oh
nigger this my first day as a woman
getting hot flashes his makeover is so
thorough not even his own children
recognize him and eventually he wins
their hearts as their strict yet lovable
caregiver mrs. Doubtfire not anymore the
only thing you’ll be watching is deep CN
n by the end of the movie he’s found out
but finds a less strange way to see his
kids
before we unveil our number one pick
here are a few honorable mentions that
woman is a woman a woman
you mean that good I must be absolutely
crazy how did I ever let it get this far
I don’t call me that
can’t help it a girl has a feeling thing
is deal you’re not a girl
details baby details I mean sorry you
have to see that but you know how it is
when you get those are manly urges huh
my name is Dorothy number one Dustin
Hoffman is Dorothy Michaels Tootsie
Michael Dorsey can’t land an acting job
for the life of him so he takes matters
into his own hands and decides to try
his luck as a woman you’re not
threatening and I’m threatening enough
how’s this you take your hands off me
Roman I need your balls right through
the roof your mass these efforts are
complicated by the relationships with
the women in his life the suitors
interested in his new persona and his
sudden jump into stardom
disqualified Hoffman’s role as Dorothy
Michaels was so spot-on it led to an
Oscar nomination
that means you dear Miss Marshall shame
on you you macho shithead do you agree
with our list what’s your favorite
cross-dressing role for more
entertaining top 10s published daily be
sure to subscribe to watchmojo.com what
are you looking at
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