Gwyneth Paltrow as Thomas Kent in Shakespeare in Love

Gwyneth Paltrow won the 1999 best actress Oscar for her role in Shakespeare in Love as a leading woman Viola De Lesseps, with whom the actor Fiennes' playing Shakespeare falls in love. He seeks inspiration while writing the classic romance Romeo and Juliet.

Gwyneth was great in the role of Viola De Lesseps. Her portrayal of a woman who nurses a dream of taking to the Elizabethan stage in a time when only men got to be actors. Besides that, she was also excellent as Thomas Kent, who masked her feminity to play a man.

She was among the few actresses who got to play both the characters with aplomb and had the critics raving about her performance and won over the audience with her flawless act. Yes, she did take help from faux facial hair, but her body language for both roles was spot on, not to forget the voice modulation. Way to go, Gwyneth!

Ted Levine as Buffalo Bill in Silence of the Lambs

Frank Theodore or Ted Levine is an American actor and is famous for playing the chilling role of Buffalo Bill in the film The Silence of the Lambs. He is also famous for his role as Leland Stottlemeyer in the television series Monk.

However, no role of his comes close to his gender-bending menacing act in Silence of the Lambs. He went into the character's skin like a pro, and we could almost imagine being in the shoes of Jodie Foster as she tries to capture the vicious serial killer.

The last few moments of the film are mind-numbingly scary thanks to the excellent acting skills of all three actors in general, namely, Jodie Foster, Anthony Hawkins in general, and Ted Levine in particular. After that, there have been many films where the villains left a deep impact on us. However, it is never a match to Ted Levine. His costumes and his body language, his voice is what makes the film memorable!

John Lithgow as Roberta Muldoon in The World According to Garp

A list of the best cross-dressing characters in films wouldn't be complete without the mention of John Lithgow in the film, The World According to Garp. There was a transgender subplot, with John Lithgow playing the transitioning football player Roberta Muldoon's role. He was fabulous in the role, and no wonder he won an Oscar nomination for the film.

The film is an adaptation of the novel by John Irving, The World According to Garp.  It is a complex film focusing on women's issues in the late 1970s.  Roberta (John Lithgow) played a transgender woman who becomes Garp's (Robin Williams) closest buddy.

He managed to hold his own in the role of a transgender person. His screen presence and acting skills became the talking point when the film hit the screens in 1982. And we cannot emphasize enough how that's no mean feat!

Jared Leto as Rayon in the Dollars Buyers Club

After his Oscar-winning portrayal of a transgender woman in the film Dallas Buyers Club, Jared Leto played many drag looks. He took on the quirky traits of the role with great elan.

Leto pulled off his role so well that he looked more breathtaking than any woman we have ever seen. Looking at him, we can say that he enjoyed it to the hilt too. He even admitted that women had to go through a lot to look a certain way, putting in hours of work.  But in the end, everything comes together perfectly after that quick dash of lipstick.

With his perfect portrayal, he went on to win the Oscar for the best supporting role. He looked the part too with his eyebrows removed, putting on a fluffy brunette wig, a willowy physique for which he dropped 30 pounds. Kudos to him for pulling off the role so well.

Barbra Streisand as Yentl in Yentl

The most striking feature of Barbra Streisand’s Yentl was distinctive owing to its cultural specificity.  The feminist undertones, unorthodox musical gave the film a distinctive edge. Streisand directed, produced, co-wrote, and starred in the film and performed in most of the nine songs featured in the film.  The film incorporates humor and music to convey the story of an Ashkenazi Jewish girl in Poland.

She dresses and lives like a boy to receive an education in Talmudic Law after the death of her father. It is very different from the kind of films people enjoy watching. It is non-homogenized, and its aesthetic value and intellectualism still set it apart from regular films.

The most difficult part for a female actor playing the role of a man and vice versa is to get the mannerisms right. And Barbara, the versatile, actress, singer, and filmmaker, got it just right.

Julie Andrews as Victor in Victor/Victoria

Victor/Victoria is a Blake Edwards-directed musical comedy film. It stars Julie Andrews, James Garner, Robert Preston, Lesley Ann Warren, Alex Karras, and John Rhys-Davies.  The film went on to earn seven Academy Awards. Besides that, it also won the Academy Award for Best Original Score. It is a remake of the 1933 German film Viktor und Viktoria.

In Victor Victoria, Julie Andrews plays the role of Victoria Grant, an unlucky singer who is also a female impersonator. So, she is playing the confusing role of a woman who pretends to be a man, pretending to be a woman.

She did play the perfect role rather perfectly. It just proves what a versatile actress Julie Andrews is. Yes, she proved to her audience, that there is more to her than sweet, girl-next-door roles.

Amanda Bynes as Sebastian in She's the Man

She's the Man is an Andy Fickman directed 2006 American romantic comedy sports flick starring Amanda Bynes, Channing Tatum, Laura Ramsey. The film draws inspiration from William Shakespeare's play the Twelfth Night. And it revolves around the life of a teenager, Viola Hastings. She tries to get into the place of her brother's new boarding school, Illyria Prep. And she goes there to secure a place in the boys' soccer team after her team gets cut from the school.

Amanda Bynes is excellent at taking on the role of her brother at his boarding school. But she has her plate full when she meets her brother's hot roommate, Duke (Channing Tatum).

The film became very popular and was a bonafide hit. Amanda got her cult following after the release of the film. Besides that, a lot of people count this as one of the cult classics by Byne. No wonder, because she was so good in the film!

Chiwetel Ejiofor as Lola in Kinky Boots

Kinky Boots dabbles real deep in the themes of diversity and tolerance when a drag queen, Lola, played to perfection by Chiwetel Ejiofor, helps a young man to save his family shoe business by catering to men who have a passion for footwear.

The story draws inspiration from true events and focuses on Charlie Price. As he inherits the shoe factory from his father, Charlie befriends cabaret performer and drag queen Lola. The duo finally discovers that they aren't too different from each other.

The Dirty Pretty Things actor later did admit it wasn't easy playing the character. And the real challenge was playing someone who strutted her stuff in six-inch heels and those clothes, but he managed to pull it off! Kudos to you, Chiwetel!

Hilary Swank as Brandon Teena in Boy's Don't Cry

Boys Don't Cry is a Kimberly Peirce-directed 1999 American biographical film. The film dramatizes the real-life story of Brandon Teena ( Hilary Swank), an American trans man who undergoes a journey of self-discovery and finding love in Nebraska. But fate intervenes and falls prey to brutal hate crime meted to her by two male acquaintances. The film also co-stars Chloë Sevigny and Lana Tisdel.

Hilary was excellent as Brandon. She also won an Oscar for her perfect portrayal of a trans man who meets tragic consequences.

Both audience and critics loved the film. And the critics raved about the sensitive handling of the subject matter and the protagonists, particularly Hilary's exemplary performance. Many critics even hailed it as one of the best films of the year (1999).

Billy Crudup as Ned Kynaston in Stage Beauty

Stage Beauty is a 2004 romantic period drama directed by the uber-talented Richard Eyre. The screenplay by Jeffrey Hatcher draws inspiration from the play written by Compleat Female Stage Beauty. This movie draws inspiration from the references made in the detailed private diary of Samuel Pepys by the 17th-century actor Edward Kynaston.

A female theatre dresser creates a revolution of sorts when she acts on stage in seventeenth-century London theatre by playing Desdemona in Othello. But when powerful people rally around her and support her, King Charles II (Rupert Everett) lifts the ban on female stage performers. And just like Maria helped Ned, she needs Ned's help to learn the role of a new profession.

The story also finds answers about the male actor she once worked for and finally replaced Billy Crudup. He plays the role pretty effortlessly, conveying the conflicts that rage in him and how he deals with them.

Anthony Perkins as Norman Bates in Psycho

Psycho, the 1960 American psychological horror-thriller film produced and directed by Alfred Hitchcock. The screenplay draws inspiration from the 1959 novel by Robert Bloch. The film stars Anthony Perkins, Janet Leigh, Vera Miles, John Gavin, and Martin Balsam. Perkins left an indelible impression on the audience as Norman Bates. Psycho wouldn't have been Psycho if it hadn't been for him.

The plot revolves around an encounter between on-the-run embezzler Marion Crane (Leigh) and shy motel proprietor Norman Bates (Anthony Perkins) and its aftermath, in which a private investigator (Balsam) investigates the cause of her death.

The last scene chills the viewers to the bones as Norman unleashes his beastly self. Norman is menacing, scary as he wears his mother's clothes and a wig and enters the cellar brandishing a chef's knife. It still gives people goosebumps.

Neil Patrick Harris as Hedwig in Hedwig and the Angry Inch

Hedwig and the Angry Inch is a rock and musical that follows Hedwig Robinson, a genderqueer East German singer of a fictional rock and roll band. The music draws inspiration from the androgynous 1970s glam rock style of David Bowie and the work of John Lennon. It explores the life of early punk performers Lou Reed and Iggy Pop.

While Neil Patrik Harris was amazing in his role, getting the femininity part right was the hardest part of the transformation for him to crack. It's tough to strut around in high heels and tougher to manage a full wig of hair and everything that comes with it.  Harris even lost a lot of weight for the role as he wanted to fit into the slip of a girly boy.

The How I Met Your Mother high-profile return to the stage as the title character in Hedwig and the Angry Inch, created quite a buzz, and why not? He was exceptional in the drag queen role.

Michael J. Fox as Marlene in Back to the Future

The film Back to the Future Part II follows Marty McFly (Fox) and his friend Dr. Emmett "Doc" Brown (Lloyd). Their time travel from 1985 to 2015 to prevent Marty's son from jeopardizing the McFly family's future forms the plot. When their arch-rival Biff Tannen (Wilson), steals Doc's DeLorean time machine and uses it to change the course of history for his benefit, the duo has to return to 1955 to restore the timeline.

In Back to the Future Part II, Michael J Fox played the role of both Marty McFly and Marty McFly's daughter, Marlene.

Michael J Fox plays Marlene McFly, the daughter of the 2015 version of Marty McFly and Jennifer Parker, and sister to Marty McFly Jr. She looks very similar to her father, doesn't she? That's because Michael J. Fox plays the role, with great aplomb. Kudos to him for essaying the role perfectly.

Guy Pearce as Adam Whitely in The Adventures of Priscilla, Queen of the Desert

The Adventures of Priscilla, Queen of the Desert is a 1994 Australian road comedy film focused on two drag queens played by Hugo Weaving and Guy Pearce and a transgender woman, played by Terence Stamp. They travel across the Australian Outback from Sydney to Alice Springs in a tour bus that they called 'Priscilla,' meeting various groups and individuals along the way.

The film's title refers to the word 'queen' as in a drag queen or female impersonator. In truth, many famous actors dressed in drag in this film, but the one or two impactful roles that made a huge impression on the audience were that of Guy Pearce and Hugo Weaving.

The guy, or rather Guy, looked quite good as a lady, and yes, can he act? You bet he can with great aplomb. The film was a big worldwide hit. It became popular mainly because its positive portrayal of LGBT individuals helped to acquaint LGBT themes to a mainstream audience.

Glenn Close as Albert in Albert Nobbs

Glenn Close, arguably, 'the greatest actress of all times,' wowed the audience as Albert Nobbs in a British-Irish drama film, Albert Nobbs. A masterpiece by director Rodrigo Garcia, this movie is everyone's all-time favorite without an iota of doubt.

The humane aspect of the story is what drew the audience to the story. Also, Genn's spectacular turn as a taciturn butler in a Dublin hotel who happens to be a woman added to the allure. In the film, Close brings to life the heartbreaking loneliness of a woman living as a man. She flawlessly portrays the struggle she experiences to find love in 19th-century Ireland.

The role was challenging for Close as Nobbs is a woman who pretends to be a man. She masked her inner turmoil with practiced stoicism and was beautifully eloquent with her eyes and body language. Indeed it was one of her outstanding performances as she got under the skin of Albert, who was trying valiantly to save herself from poverty.

Cate Blanchett as Jude Quinn in I'm Not There

Cate Blanchett plays Jude Quinn in a riff on electric guitar 60s counter-revolutionary Bob Dylan. I'm Not There is a Todd Haynes-directed 2007 biographical musical film draws inspiration from the life and career of the revolutionary American singer-songwriter Bob Dylan.

Six actors depict Bob Dylan's public personas: Cate Blanchett, Richard Gere, Christian Bale, Marcus Carl Franklin, Heath Ledger, and Ben Whishaw. The film came into much praise, and particular praise came to Cate Blanchett for her scintillating performance. It won her the Volpi Cup from the Venice Film Festival, the Golden Globe Award.

Besides that, she also got an Academy Award nomination for Best Supporting Actress. No wonder, as Cate managed to bring a new and fresh take on Bob Dylan's life with her excellent acting skills. Kudos to Cate for pulling off the role even as she competed with five other actors playing the same personality.

Angelina Jolie as Evelyn Salt in Salt

One interesting tidbit on the movie, Salt , initially went to Tom Cruise. But after many discussions. He turned down the role as he felt it was too close to his Mission: Impossible series. The role finally went to Angelina as Amy Pascal, the executive producer of Columbia Pictures, did the unthinkable and changed the film's protagonist from male to female.

Angelina Jolie, played Evelyn Salt is a CIA operative accused of being a Russian sleeper agent. She had to go on the run away from her colleagues as she investigates to clear her name. And while at it, she also tries to find her missing husband. Things become complicated as her past is revealed and Salt's loyalties are questioned.

Angelina plays the role of perfection as she fights tooth and nail to clear her name and dons various looks and disguise for the same. In one of her looks, she plays a tough as nails naval officer, and she is oh-so-good in that.

Patrick Stewart as Walter Blunt in Blunt Talk

Stewart plays a newscaster in Blunt Talk, a show made by Seth MacFarlane. It was everything that Patrick had not ever attempted to do, taking weirdness to a whole new level. He played a no-holds-barred bacchanalia one would take care to avoid in polite company.

The show follows the life of a British newscaster, Walter Blunt, who moves to Los Angeles to conquer American nightly cable news. However, he falters in the path, and his several misguided decisions on and off the air prove that it would be difficult for him to realize his ultimate dreams.

Blunt's name was taken from one of the minor characters of Sir Walter Blunt in William Shakespeare's Henry IV, Part 1. While Stewart donned many roles, playing a drag queen was difficult, complete with over-the-top hair, makeup, costumes, and heels. He pulled it off with great flair.

Eddie Redmayne as Elbe in the Danish Girl

Playing the role of a transgender person is never easy. However, Eddie Redmayne pulled it off in The Danish Girl, Eddie Redmayne took pains to build the character from the inside out. He studied Lili Elbe's pseudo-autobiography Man Into Woman to prepare for the role. He even went to meet separately with six transgender women from different generations to know all about their experiences.

The Danish Girl is a 2015 biographical romantic drama film and draws inspiration from the life of Danish painters Lili Elbe and Gerda Wegener. Eddie Redmayne as the Elbe, who was one of the first known recipients of a body reassignment surgery.

Redmayne's performance received a lot of praise, and he even earned an Academy Award nomination for the role. This film gave us glimpses of Eddie Redmayne's phenomenal acting skills. The appreciation and applause he received for the role were completely well-deserved.

Cillian Murphy as Kitten in Breakfast on Pluto

Breakfast on Pluto is a comedy-drama film starring Cillian Murphy as a transgender person, Kitten. It explores Kitten's journey in search of love, her long-lost mother in small-town Ireland and London in the 1970s.

Cillian Murphy did not disappoint anyone with his performance. Murphy could even give women a run for their looks as his performance as Kitten and his costume and makeup was flawless.

Playing a transvestite woman is far removed from his usual portrayal of gangsta Tommy Shelby in Peaky Blinders. He's not only convincing, but also pulls off the role of a girl with delicate nature and innocent air to the T. The film, was poignant, effervescent, albeit a tad eccentric. And we could say that his performance was heartfelt and gave a clear portrayal of a lost soul trying to find his past.

Jason Isaacs as Chaz Watley in Sweet November

Sweet November is a 2001 American romantic drama film based in San Francisco. It features Keanu Reeves and Charlize Theron, and Jason Isaacs. However, Jason did not play the lead. Instead, he gave strong support as Sara's downstairs neighbor Chaz.

He may play the stereotypical gay best buddy who was ever ready to lend pithy retort, but he does it well. Isaac's character has several secrets that amp the film's interest value and ensures an interesting interaction with Reeves' character.

Jason ensured the character was breezy, fun, and easy-on-the-eye too! Well, it turns out to be some of the more memorable drag roles of mainstream actors who go beyond the conventional to try something completely different and non-stereotypical. Kudos to the actor for doing such a good job! We hope to see him playing more such interesting roles in the future.

Willem Dafoe as Paul Smucker in The Boondock Saints (1999)

William James Dafoe, is popular by his professional name Willem Dafoe. He has displayed amazing acting skills in almost all the movies he has been a part of. His filmography includes Once Upon a Time in Mexico, Murder on the Orient Express, Spider-Man, The Boondock Saints, and many others. He has joined hands with several renowned filmmakers to gift us some fabulous work on celluloid over the years.

Willem has earned enough wealth in his life to stay away from any financial headache. His role in the 1999 film, The Boondock Saints will hold a special place in every fan's heart. Willem plays a special agent working for the FBI who is inclined towards men.

The part of the plot where he switches loyalties is brilliant. It is one of his must-watch performances.  Willem has always been an asset to the film industry ever since he stepped into it.

Ving Rhames as Holiday Heart in Holiday Heart (2000)

A successful acting career has provided him financial security for sure.  Irving Rameses Rhames, or just Ving Rhames, grabbed the limelight with his portrayal of Luther Stickell in the iconic Mission: Impossible franchise. Side by side, he also gained recognition as Marsellus Wallace in the 1994 flick, Pulp Fiction.

His ensemble of films also includes Out of Sight, Bringing Out the Dead, Striptease, and Holiday Heart. The 2000 television film, Holiday Heart, presented Ving Rhames quite differently from the way we are familiar with. Ving's fans probably never saw him play a drag queen before.

His character, Danny Glover, aka Holiday Heart, becomes friends with a single mother and her daughter and does everything to protect them from an environment of animosity and hatred. It’s needless to say that this was one of his best performances to date.

Tyler Perry as Madea in Diary of a Mad Black Woman (2005)

Tyler Perry is an actor, screenwriter, director, and producer. He found a mention in the list of the highest-paid star in entertainment by Forbes magazine in 2011. Between 2010 and 2011, Tyler had over $130 million in his bank account. Well, that's massive.

After all, talents like Tyler never go unnoticed. He is truly an asset to the industry and a terrific performer as well. His role of a drag queen in the 2005 comedy-drama, Diary of a Mad Black Woman received rave reviews and earned him applause and acclamation.

It happens to be his debut project. Tyler played the role of Mabel ‘Madea’ Simmons to such perfection, that he could lead the audience to forget that it was him playing the role. Only actors with this level of brilliance can accomplish such things. Kudos to you, man!

Tom Hanks as Buffy in Bosom Buddies (1980)

Tom Hanks doesn't need any introduction, does he? The legendary Hollywood actor is one of the finest performers ever to have graced the silver screen in the history of the film industry.

His repertoire of films comprises  You've Got Mail, Saving Private Ryan, Cast Away, Bridge of Spies, and several others. No wonder, he has laid his hands on numerous awards to date, and his banks have always jingled with the currency he has earned.

He played dual roles in the much popular 1980 television sitcom on the ABC network, Bosom Buddies – one that of Kip Wilson and the other that of Buffy, the role of a woman he disguises himself in. Tom carried off the roles with elan and proved his potential. It was during his initial years, but he was, no doubt, brilliant.

Tim Curry as Doctor Frank-N-Furter in The Rocky Horror Picture Show (1975)

Tim Curry has dabbled in films, television, and theater and often plays villainous roles. He has received a lot of appreciation for his work in Home Alone 2: Lost in New York, The Three Musketeers, Peter Pan & the Pirates, Star Wars: The Clone Wars,, etc.

But it was his portrayal of Doctor Frank-N-Furter in the 1975 film, The Rocky Horror Picture Show was the one that gave him the breakthrough. His role was that of a cross-dresser scientist who had an interest in both males and females.

He pulled off the role with his raw talent and stole the hearts of both the critics and fans alike. His ability to carry any character on his shoulders has accentuated his credibility as an actor. Besides that, it also shot his net worth significantly, keeping him away from any financial tensions. Tim has also churned out three studio albums as Simplicity, Fearless, and Read My Lips.     

Stephen Dorff as Candy Darling in I Shot Andy Warhol (1996)

Stephen has been brilliant in almost all the roles he has portrayed. This includes the role of Roland West in True Detective, Stuart Sutcliffe in Backbeat, and so on. We all have loved his work in films such as Blood and Wine, Den of Lions, Cecil B. Demented, Tomorrow You're Gone, etc.

However, his performance as Candy Darling in the 1996 movie, I Shot Andy Warhol stands out. The British-American film revolved around the relationship that radical feminists, Valerie Solanas, shared with the artist, director, and producer Andy Warhol.

Stephen as the Warhol superstar with an expression that wasn’t in any way related to his gender, had a key role to play, and he certainly came out with flying colors. Candy shot for many of Warhol’s films like Women in Revolt and Fresh. The project certainly gave Stephen’s savings the much-needed boost and made him a household name.

Shawn Wayans and Marlon Wayans as FBI Agents in White Chicks (2004)

Shawn Wayans has had his fingers in many pies. He is an actor, producer, comedian, writer, and DJ who has many achievements to his credit. He has been a part of several comedy films such as Little Man, Scary Movie, Don't Be a Menace, Scary Movie 2, etc.

Joining his hands with brother Marlon Wayans, Shawn has written and starred in The Wayans Bros. Marlon has also been quite an accomplished actor, starring in Fifty Shades of Black, A Haunted House, A Haunted House 2, as well as Joe: The Rise of Cobra. The siblings also appeared together in the 2004 comedy, White Chicks.

The duo portrayed two FBI agents who disguised themselves as women and worked undercover to get to the bottom of a kidnapping plot. Their respective roles gave them the security they needed on the financial front.

Robin Williams as Mrs. Euphegenia Doubtfire in Mrs. Doubtfire (1993)

Robin Williams caught everyone's fancy when he ventured into the world of stand-up comedy in the mid-70s and attained popularity with his portrayal as Mork in Mork & Mindy, the sitcom. He played numerous roles in various films, and his acting prowess soon led everyone to hail him as one of the best comedians ever.

One of Williams' iconic performances was that of Mrs. Euphegenia Doubtfire in the 1993 comedy, Mrs. Doubtfire. It narrates the story of a divorced actor who disguises himself as a female to take up a job at his former wife's place. He attempts to stay close to his children and what follows is a rib-tickling journey.

William’s fabulous acting helped the film bag an Academy Award in the Best Makeup category. The makers did rake in some hefty returns on the investment they made on this classic.

Patrick Swayze as Vida Boheme in To Wong Foo Thanks for Everything, Julie Newmar (1995)

Patrick Swayze might not be amongst us anymore, but his legend will continue to live till the end of time. The actor left for his heavenly abode in the year 2009. But his fans from all over the world do have fond memories that they will cherish forever.

He set the screen on fire with his tough roles and touched the strings of our hearts with the romantic ones. Among the films that he received Golden Globe nominations for, To Wong Foo, Thanks for Everything, Julie Newmar, deserves a special mention.

The way he transformed himself and stepped into the shoes of a drag queen, Vida Boheme, is praiseworthy. He was so convincing in the role that the audience was in for confusion. A lot of them believed that it was Patrick essaying the character. This was all due to his sheer talent. Therefore, he was immensely successful and was financially strong enough to avoid a refinance.

Wesley Snipes as Noxeema Jackson in To Wong Foo Thanks for Everything, Julie Newmar (1995)

Wesley Snipes has been a man of many talents. He has proved his worth as an actor, author, film producer, and martial artist. He has played integral roles in various films such as White Men Can’t Jump, Demolition Man, The Expendables 3, and the Blade trilogy.

Though he has been an outstanding performer in all the films, he has appeared that one movie that stands out in his career is To Wong Foo, Thanks for Everything, Julie Newmar. He starred as Noxeema Jackson, a drag queen, in the 1995 flick, alongside Patrick Swayze, who played Vida Boheme.

Noxeema and Vida’s partner-in-crime and Wesley’s punch into the character made this film a must-watch. The combination of Wesley and Patrick was a treat for the fans and Wesley ensured that enough goes into his bank account after the film so that he can fill up his savings account.

Nathan Lane as Albert Goldman in The Birdcage (1996)

Nathan Lane has enjoyed a long career of 45 years, and his whole journey has been decorated with his excellent work on the stage, the small screen, and the big screen as well. He has a People's Choice Award, two Daytime Emmys, and has one Screen Actors Guild Award under his belt.

Nathan has been honored with an induction into the prestigious American Theater Hall of Fame and has a star in his name on the esteemed Hollywood Walk of Fame. Nathan Lane played the role of Albert Goldman in the 1996 comedy, The Birdcage.

Albert was the partner of Armand Goldman, the owner of a drag club, The Birdcage, and was famous for his flamboyant and effeminate nature. Aside from Robin Williams' performance as Armand, Nathan's enactment of Albert was surely another highlight of the movie. The film went on to be a grand success.

Martin Lawrence as Hattie Mae "Big Momma" Pierce in Big Momma’s House (2000)

Martin has displayed stupendous skills as an actor, comedian, talk show presenter, and a former boxer. He rose to prominence as a lead actor in the 90s decade. His portrayal of Maurice Warfield in the ABC sitcom, What's Happening Now!!

His work in Wild Hogs, A Thin Line Between Love and Hate, House Party, and Big Momma's House ensured that he would never have to appoint a bankruptcy lawyer at any point in his career. Big Momma's House was a special project for Martin.

He played the role of an agent from the FBI who had to disguise himself as an overweight elderly lady and carry out a covert operation. The film was a landmark in Martin’s journey as an actor. Though critics didn’t quite like the movie, Martin’s performance received appreciation from all quarters. Big Momma’s House was a success at the box-office.

Kurt Russell as Lieutenant Gabriel "Gabe" Cash in Tango & Cash (1989)

Kurt Russell has always had a special place in our hearts. The underrated actor has never won an award, but no one can doubt that his abilities to outperform many actors on a given day. Among his vastly impressive resume, Kurt has worked in films like Escape from L.A., The Fast and the Furious series, Once Upon a Time in Hollywood, and Tango & Cash.

While talking about Tango & Cash, the 1989 action flick, Kurt (Cash) paired up with Sylvester Stallone (Tango) and delivered a kick-ass performance. Do you remember the sequence where Cash dresses up as a female, and Tango's sister (Teri Hatcher) helps him escape from the nightclub after being surrounded by the cops?

Kurt won positive reviews for that and accentuated his earnings. Well, that was one of the major highlights of this story about two LAPD detectives.

Jude Law as Minx in Rage (2009)

When you talk about the most talented stars from Hollywood, the name of Jude Law is bound to crop up. With multiple awards and nominations to his name, Law doesn't need to prove his mettle as an actor.

Road to Perdition, Fantastic Beasts: The Crimes of Grindelwald, Sherlock Holmes as well as Sherlock Holmes: A Game of Shadows, are some of his films that have made his bio-data a brilliant one. As a result, his financial advisor has been having quite a busy time, managing all his money.

In Rage, the 2009 satirical mystery, we saw a new side of Law and that is his feminine side. He dressed up as a beautiful and sensuous supermodel and truly speaking, he was hardly unrecognizable. With a black wig, scarlet lipstick, and a stunning strapless dress, he looked simply out of the world.

Johnny Depp as Bon Bon in Before Night Falls (2000)

Johnny Depp is one of the most versatile actors ever to have worked in Hollywood. Banking on his electric performances, Depp has been flooded with accolades and various nominations. He made his debut with A Nightmare on Elm Street in 1984 and burst into the big league with his role in 21 Jump Street.

His filmography also includes Charlie and the Chocolate Factory, Alice in Wonderland, Public Enemies, and the iconic Pirates of the Caribbean film series. But, we can't simply leave out the 2000 film, Before Night Falls.

In the biographical romantic flick, we saw Depp playing the dual role of first Bon Bon, a man who loves to dress up and behave like a woman, and then as the prison interrogator, Lieutenant Victor. Depp looks glamorous as Bon Bon, and that spoke volumes about his credentials as a performer.

John Travolta as Edna Turnblad in Hairspray (2007)

American singer and actor Travolta made remarkable progress in his career during the 1970s. He appeared on Welcome Back Kotter, the TV sitcom, and starred in several box office successes like Saturday Night Fever, Carrie, and Grease, to name a few.

Despite his acting career suffering a blow in the 1980s, he made a great resurgence in the 1990s, thus consolidating his finances. With films like Broken Arrow, Get Shorty, Pulp Fiction, Face/Off, Swordfish, and more. And over the years, he continued to win hearts and thus adding to his list of film awards. In Hairspray, a 2007 musical romantic comedy, he did a fantastic job.

As Edna Turnblad, a laundry business owner and Tracy’s mother, Travolta ensured he delivered a performance that dragged the portrayal of the original 1988 film.  John was in fact the most coveted actor for this role, as producers Neil Meron and Craig Zadan rooted for him the most.

Jamie Farr as Corporal Maxwell Q. Klinger in MAS*H (1972)

The American TV star who is in his mid-80s is one of the most notable theatre artists and film comedians. Most popular for essaying the role of Corporal Maxwell Q. Klinger in M*A*S*H, the CBS TV sitcom. The popularity of the show won him a place in the Hollywood Walk of Fame in 1985.

Alongside Alan Alda, Jamie Farr was one of the main cast members in the US Army in South Korea. In his role, he served as an orderly or sentry. He was the first main character in the series who did not appear in the original movie or the successive movies.

Jamie was brilliant in his role. Going by the character's requirements, he habitually wore clothing for women and even performed 'crazy' stunts! While there's no doubt that Farr made a lot of earnings, but perhaps no one would have been even close to how he had portrayed his character.

Hugo Weaving as Mitzi Del Bra in The Adventures of Priscilla, Queen of the Desert (1994)

English actor Hugo Wallace Weaving was born in Colonial Nigeria. His parents were English, but he stayed in Australia throughout his professional career. The 60-year old man has also been the recipient of six Australian Academy of Cinema and TV Arts Awards.

Hugo was splendid in film roles like The Matrix trilogy, The Hobbit, V for Vendetta, and Captain America: The First Avenger. He also did several voiceover roles, like Babe, Happy Feet, Happy Feet Two, and the Transformers series.

Weaving ensured he was the perfect match to Anthony in The Adventures of Priscilla, Queen of the Dessert. The 1994 road comedy film, written and directed by Stephan Elliott, became a surprise hit worldwide. Alongside some of the biggest awards, it received a lot of critical appreciation from far and wide. With whatever he earned via this film, it requires no second mention that the actor notched up great investments.

Eddie Murphy as Mama and Grandma Klump in The Nutty Professor (1996)

Eddie Murphy has wowed everyone with his acting prowess ever since he started his journey in the tinsel town. He grabbed attention as a cast member of the late-night variety show, Saturday Night Live. His comic timing has led Comedy Central to include him in the list of 100 greatest stand-ups ever.

Eddie has been fantastic in movies such as Vampire in Brooklyn, Coming to America, The Nutty Professor, and the iconic Shrek franchise. Many of you will surely remember his amazing portrayal of Grandma Klump in the 1996 flick, The Nutty Professor.

With his abilities to carry off any role he has been assigned, Eddie played the role of Grandma Klump to perfection. He was so convincing in the role that the audience couldn’t stop themselves from going gaga over him. The film certainly fattened his bank account after the release.

Dustin Hoffman as Dorothy Michaels in Tootsie (1982)

There is probably no Hollywood fan who doesn't know who Dustin Hoffman is. With his versatile portrayals of characters, whether it's an anti-hero or an emotionally vulnerable one, Dustin has swept the audience off their feet time and again.

His filmography comprises Kramer vs. Kramer, The Graduate, Rain Man, and Tootsie, among various others. Among all the awards he has won, there is the Primetime Emmy Award, the British Academy Film Award, the Golden Globe Award, and of course, the Academy Award. You remember Dorothy Michaels from Tootsie, don't you?

Dustin played the role of Michael Dorsey, who dresses up as a woman and takes up the name of Dorothy Michaels to audition for a role and eventually gets it. You don't need us to tell you that he was out-of-the-world. The 1982 film paved the way for handsome net worth for Dustin.

Adam Sandler as Jill Sadelstein in Jack and Jill (2011)

Adam Sandler became a prominent face right from when he appeared on Saturday Night Live, one of the most-watched shows on TV. He capitalized on his fame and starred in numerous blockbusters like Grown Ups, The Wedding Singer, Jack and Jill, Uncut Gems, etc.

Amongst all his works, we can't help but mention Adam's performance in the 2011 comedy Jack and Jill. And this happens to be one of his finest to date, which won the hearts of the audience and critics alike. After all, not many actors can carry the roles of both Jack and Jill, the fraternal twins, with such confidence.

We couldn't believe our eyes that we were seeing the same individual in both roles. Adam cemented his position in the industry with this one. And the success of the movie made sure that he does not need a bankruptcy lawyer in this lifetime.