Most Popular Cross Dressing Movies and TV Shows
- Movies or TV
- IMDb Rating
- Instant Watch Options
- In Theaters
- On TV
- Release Year
51. House of Lies (2012–2016)
TV-MA | 28 min | Comedy, Drama
A subversive, scathing look at a self-loathing management consultant from a top-tier firm. Marty, a highly successful, cutthroat consultant is never above using any means (or anyone) necessary to get his clients the information they want.
R | 104 min | Comedy, Music
Two drag performers and a transgender woman travel across the desert to perform their unique style of cabaret.
Votes: 44,022 | Gross: $11.22M
55. Wild Wild West (1999)
PG-13 | 106 min | Action, Comedy, Sci-Fi
The two best special agents in the Wild West must save President Grant from the clutches of a diabolical, wheelchair-bound, steampunk-savvy, Confederate scientist bent on revenge for losing the Civil War.
Votes: 146,700 | Gross: $113.81M
56. The Black Dahlia (2006)
R | 121 min | Crime, Drama, Mystery
Two policemen see their personal and professional lives fall apart in the wake of the "Black Dahlia" murder investigation.
Votes: 69,198 | Gross: $22.52M
57. Just One of the Guys (1985)
PG-13 | 100 min | Comedy, Romance
Terry feels discriminated against when the summer jobs at Sun Tribune go to 2 guys. She decides to do something about it. She dresses like a guy and gets a haircut. Will students at the other high school notice? Girls notice "him".
Votes: 12,776 | Gross: $11.50M
58. The Hot Chick (2002)
PG-13 | 104 min | Comedy, Fantasy
An attractive and popular teenager, who is mean-spirited toward others, finds herself in the body of an older man, and must find a way to get back to her original body.
Votes: 86,139 | Gross: $35.08M
61. The Fisher King (1991)
R | 137 min | Comedy, Drama, Fantasy
A former radio DJ, suicidally despondent because of a terrible mistake he made, finds redemption in helping a deranged homeless man who was an unwitting victim of that mistake.
Votes: 74,893 | Gross: $41.90M
62. The Witcher 3: Wild Hunt (2015 Video Game)
M | Action, Adventure, Drama
Geralt of Rivia, a monster hunter for hire, embarks on an epic journey to find his former apprentice, Ciri, before The Wild Hunt can capture her and bring about the destruction of the world.
63. Velvet Goldmine (1998)
R | 118 min | Drama, Music
In 1984, British journalist Arthur Stuart investigates the career of 1970s glam superstar Brian Slade, who was heavily influenced in his early years by hard-living and rebellious American singer Curt Wild.
Votes: 32,271 | Gross: $1.05M
64. The Limehouse Golem (2016)
Not Rated | 109 min | Crime, Mystery, Thriller
In Victorian London, a Scotland Yard inspector hunts down the sadistic killer behind a series of gory, Jack the Ripper-Like murders.
65. The Passion of Joan of Arc (1928)
Not Rated | 114 min | Biography, Drama, History
In 1431, Jeanne d'Arc is placed on trial on charges of heresy. The ecclesiastical jurists attempt to force Jeanne to recant her claims of holy visions.
Votes: 42,402 | Gross: $0.02M
66. Insidious: Chapter 2 (2013)
PG-13 | 106 min | Horror, Mystery, Thriller
The Lamberts believe that they have defeated the spirits that have haunted their family, but they soon discover that evil is not beaten so easily.
Votes: 145,582 | Gross: $83.59M
67. Norbit (2007)
PG-13 | 102 min | Comedy, Romance
A mild-mannered guy, who is married to a monstrous woman, meets the woman of his dreams, and schemes to find a way to be with her.
Votes: 64,487 | Gross: $95.67M
68. The Scorpion King (2002)
PG-13 | 92 min | Action, Adventure, Fantasy
A desert warrior rises up against the evil army that is destroying his homeland. He captures the enemy's key sorcerer, takes her deep into the desert and prepares for a final showdown.
Votes: 125,126 | Gross: $91.05M
69. Martin (1992–1997)
TV-PG | 30 min | Comedy, Drama, Romance
Sassy sitcom centering on radio and television personality Martin Payne. Series focuses on his romantic relationship with girlfriend Gina, her best friend Pam and escapades with best friends Tommy and Cole.
71. Walk of Shame (2014)
R | 95 min | Comedy
A reporter's dream of becoming a news anchor is compromised after a one-night stand leaves her stranded in downtown L.A. without a phone, car, ID or money - and only 8 hours to make it to the most important job interview of her life.
Votes: 48,930 | Gross: $0.04M
72. All I See Is You (2016)
R | 109 min | Drama, Mystery, Romance
A blind woman's relationship with her husband changes when she regains her sight and discovers disturbing details about themselves.
Votes: 9,299 | Gross: $0.22M
73. Stage Beauty (2004)
R | 106 min | Drama
A female theatre dresser creates a stir and sparks a revolution in seventeenth century London theatre by playing Desdemona in Othello. But what will become of the male actor she once worked for and eventually replaced?
Votes: 9,631 | Gross: $0.78M
74. The Three Stooges (2012)
PG | 92 min | Comedy, Family
While trying to save their childhood orphanage, Moe, Larry and Curly inadvertently stumble into a murder plot and wind up starring in a reality television show.
Votes: 28,928 | Gross: $44.34M
75. 100 Girls (2000)
R | 94 min | Comedy, Romance
Matt spends the night with a girl in an elevator during power outage in a girls' college dorm. He never sees her. Waking up in the morning, panties are all that's left of her. How does he find her in a building with 100 girls?
76. Casanova (2005)
R | 112 min | Adventure, Comedy, Drama
The fabled romantic Giacomo Casanova, after failing to win the affection of the Venetian woman Francesca Bruni, strives to discover the real meaning of love.
Votes: 50,119 | Gross: $11.29M
78. Malibu Express (1985)
R | 105 min | Comedy, Crime, Mystery
A womanizing private detective is assigned the task of investigating who is behind the hi-tech computer technology leaks to the Russians.
79. Pee-wee's Big Adventure (1985)
PG | 91 min | Adventure, Comedy, Family
When eccentric man-child Pee-wee Herman gets his beloved bike stolen in broad daylight, he sets out across the U.S. on the adventure of his life.
Votes: 47,235 | Gross: $40.90M
80. All Good Things (2010)
R | 101 min | Crime, Drama, Mystery
Mr. David Marks was suspected but never tried for killing his wife Katie who disappeared in 1982, but the truth is eventually revealed.
Votes: 50,511 | Gross: $0.58M
81. Dead Man (1995)
R | 121 min | Drama, Fantasy, Western
On the run after murdering a man, accountant William Blake encounters a strange Native American man named Nobody who prepares him for his journey into the spiritual world.
Votes: 85,463 | Gross: $1.04M
82. Madea's Family Reunion (2006)
PG-13 | 107 min | Comedy, Drama, Romance
While planning her family reunion, a pistol-packing grandma must contend with the other dramas on her plate, including the runaway who has been placed under her care, and her love-troubled nieces.
Votes: 10,238 | Gross: $63.26M
83. The Flowers of War (2011)
R | 146 min | Drama, History, Romance
An American finds refuge during the 1937 Japanese invasion of Nanking in a church with a group of women. Posing as a priest, he attempts to lead the women to safety.
Votes: 46,686 | Gross: $0.01M
85. Breakfast on Pluto (2005)
R | 128 min | Comedy, Drama
In the 1970s, a young trans woman, Patrick "Kitten" Braden, comes of age by leaving her Irish town for London, in part to look for her mother and in part because her gender identity is beyond the town's understanding.
Votes: 19,991 | Gross: $0.83M
86. Victor Victoria (1982)
PG | 134 min | Comedy, Music, Musical
A struggling female soprano finds work playing a male female impersonator, but it complicates her personal life.
Votes: 18,311 | Gross: $21.93M
88. The Flintstones in Viva Rock Vegas (2000)
PG | 90 min | Comedy, Family, Romance
In this live-action prequel to The Flintstones (1994), the Flintstones and the Rubbles go on a trip to Rock Vegas, where Wilma Slaghoople (Kristen Johnston) is pursued by playboy Chip Rockefeller (Thomas Gibson).
Votes: 20,054 | Gross: $35.27M
89. Head in the Clouds (2004)
R | 132 min | Drama, Romance, War
From the roaring 1920s to the ruinous Spanish Civil War and Adolf Hitler's rise into power, the lives of an Irish schoolteacher, a provocative heiress and her Spanish muse are intricately interlaced, sharing the same destiny and passion.
Votes: 14,122 | Gross: $0.40M
91. Bad Grandpa (2013)
R | 92 min | Comedy
86-year-old Irving Zisman takes a trip from Nebraska to North Carolina to take his 8 year-old grandson, Billy, back to his real father.
Votes: 86,682 | Gross: $102.00M
92. Orlando (1992)
PG-13 | 94 min | Biography, Drama, Fantasy
Young nobleman Orlando is commanded by Queen Elizabeth I to stay forever young. Miraculously, he does just that. The film follows him as he moves through several centuries of British ... See full summary »
Votes: 12,661 | Gross: $5.29M
94. Thunderbolt and Lightfoot (1974)
R | 115 min | Comedy, Crime, Drama
With the help of an irreverent young sidekick, a bank robber gets his old gang back together to organize a daring new heist.
Votes: 20,706 | Gross: $25.00M
95. Black Lagoon (2006)
TV-MA | 25 min | Animation, Action, Adventure
A Japanese businessman, captured by modern-day pirates, is written off and left for dead by his company. Tired of the corporate life, he opts to stick with the mercenaries that kidnapped him, becoming part of their gang.
96. Big Momma's House (2000)
PG-13 | 99 min | Action, Comedy, Crime
In order to protect a beautiful woman and her son from a robber, a male FBI agent disguises himself as a large grandmother.
Votes: 77,424 | Gross: $117.56M
99. Little Britain (2003–2006)
TV-MA | 29 min | Comedy
Matt Lucas and David Walliams, the creators of this character-comedy sketch show, delight in all that is mad, bad, quirky and generally bonkers about the people and places of Britain.
100. Shaolin Soccer (2001)
PG | 87 min | Action, Comedy, Fantasy
A young Shaolin follower reunites with his discouraged brothers to form a soccer team using their martial art skills to their advantage.
Votes: 70,370 | Gross: $0.49M