My addition to your list would be Martin Lawrence in the Big Momma’s House series. Though some scenes are ham-handed and are sheer slapstick, Martin Lawrence has to be given credit for playing Hattie Mae Pierce, that singular house help who doubles as an FBI agent, superwoman nanny and caretaker. Whether it is struggling to fit into Hattie’s massive silicon mould, or hiding from his girlfriend, Martin has all our sympathy. And genuine applause when he has to resort to karate chops while dealing with the bad guys even while struggling with wigs, frocks, an enormous girth and fake face moulds. (Add to the list of male actors who played memorable women on the big screen... August 25)

Pampa Paul

The list of male actors who played memorable women on the big screen is incomplete without Vijay Sethupathi playing a transgender in Thiagarajan Kumararaja’s path-breaking film Super Deluxe which deserves more than one watch to understand the depth of each character.

Cillian Murphy in Breakfast on Pluto

Sethupathi plays Shilpa, a transperson, who goes back to their wife and son after seven years. His segment in this ensemble film features his wife and son questioning gender dynamics and one’s basic freedom to choose who he or she wants to make us sit up and ponder. Scenes between Sethupathi and his son go beyond father-son bonding, and Kumararaja makes us understand that it is perfectly alright to embrace who we are. Vijay Sethupathi makes us empathise with his transwoman character with restraint and sensitivity. In one scene, as Shilpa comes out of the room after being sexually assaulted, her little son asks her “Adichaangala (Did they beat you)?” Shilpa, wiping her tears, says, “Yes”. He then asks, “What did you do in response?” Shilpa subtly puts, “Kadichaen (I bit).” If the movie is a psychedelic trip, then Sethupathi is ecstasy!

Dyutiman Bhattacharya

My fondest male actor playing a woman will always be Robin Williams in Mrs. Doubtfire (1993), owing to his seminal performance, as pointed out by t2. It is also the role of a remarkable dad that, albeit being a comic one, shows us how far a father’s love towards his children can take him. Another memorable performance on this list is Cillian Murphy’s portrayal of Patrick “Kitten” Braden in Breakfast on Pluto (2005), a complex and nuanced character. Murphy does a remarkable job playing a transgender person who navigates their way through a tumultuous, and often hostile world blending resilience, innocence and self-discovery. He captures the essence of a person who deals with a society that often fails to understand, let alone appreciate them. The performance brings depth, empathy and authenticity to a character who embodies the complexities of identity, resilience and the pursuit of happiness.

Arjun Kapoor in Sandeep Aur Pinky Faraar

In Indian cinema, Shreyas Talpade is one Bollywood actor who has flawlessly nailed each one of his female avatar scenes on screen. His performances in movies like Paying Guests (2009) along with Jaaved Jafferi, and Golmaal Returns (2008) in a comical sequence about Women’s Day at a shopping mall with Ajay Devgn, Tusshar Kapoor and Arshad Warsi, showcase his versatility as an actor. Talpade’s ability to portray women with finesse deserves appreciation.

Camellia Paul

In cinema, the portrayal of women characters by male actors draws praise as well as backlash from the masses. Despite the mixed reactions, many such portrayals become memorable and form a part of pop culture. One such spectacular performance was delivered by Martin Lawrence in the comedy film series Big Momma’s House. His character Malcolm Turner is a top FBI agent and is known as the master of disguise. In his latest mission to nab a criminal, he disguises himself as a vivacious old woman and attempts to search for information about a robbery. Dressed in a pretty red polka-dot dress with blonde, curly hair, the character was frenzied, emotional and packed with humour, making the audience laugh in even some of the most tense scenes of the film. Martin Lawrence portrayed the high-spirited character with flamboyance and fun and retained the character’s essence throughout the series.

Aayman Anwar Ali

Terence Stamp, Hugo Weaving and Guy Pearce in The Adventures of Priscilla, Queen of the Desert (1994), a movie telling the story of three drag queens portrayed by the three actors. Sparkling costumes, songs, wit and charm, comedy and the cast’s performances are nothing less than perfect. Big Momma’s House series in which Martin Lawrence, an FBI agent, goes undercover as the larger-than-life grandmother of his love interest to solve crimes, is insanely funny and Lawrence’s portrayal of the cantankerous Southern granny Big Momma makes it a joy to watch. Michael J. Fox in Back to the Future Part II (1989) where he hilariously plays multiple characters, including his daughter.

Ramyani Sanyal

I can’t really add to the list, as it already covers some of the most remarkable ones I have seen (fave being Kamal Haasan as the inimitable Chachi). A certain portion of a film has stayed with me, though. It features a tough(ened), disillusioned and yet tender-hearted Haryanvi cop called Satinder ‘Pinky’ Dahiya who dons the robes and make-up of a cross-dresser to dance his way through a Pithoragarh wedding procession and out-of-reach of a bunch of corrupt cops hot on his trail, as they haplessly look on. The sequence just prior is especially poignant, when, after all they had been through together, Pinky tells Sandeep within the cover of the back of a goods truck, that if she were to ever commit a criminal act, it should be top-notch, or else she’d end up just like him. The entire act is funny, ironically real yet extremely moving and human. It leaves a bittersweet feeling in the mind of the viewer. Both Arjun Kapoor (as Pinky) and Parineeti Chopra (as Sandy) really shine in that sequence, one of many in a really underrated film (Sandeep Aur Pinky Faraar).

Akshay Kumar in Laxmii

Krishna Kumar

Adding to the list of male actors dressed as women are Rishi Kapoor and Paintal in Rafoo Chakkar; Govinda in Aunty No. 1 and also Ajay Devgan, Tusshar Kapoor, Shreyas Talpade and Arshad Warsi in a small scene in Golmaal Again.

Mohua Sen Dasgupta

In the 1959 American movie Some Like It Hot, directed by Billy Wilder, Tony Curtis and Jack Lemmon play Joe and Jerry, two musicians who disguise themselves by cross-dressing as women to escape from mafia gangsters they saw committing a crime. Joe and Jerry take up the identities of two women named Josephine and Daphne respectively. They join an all-female band who are headed to Miami by train. On the train, they befriend Sugar Kane (Marilyn Monroe), the band’s vocalist and ukulele player.

Once in Miami, Joe woos Sugar by assuming a second disguise as a millionaire, Junior. On the other hand, an actual millionaire Osgood (Joe E. Brown) falls for and proposes marriage to ‘Daphne’. At the end of the film, Jerry declares he cannot marry Osgood because he is a man. In reply, Osgood says the iconic line, “Well, nobody’s perfect”.

Both Curtis and Lemmon did a great job playing women and the make-up artists should also be lauded for their brilliant efforts.

Kushangkur Das

I will fondly remember the legendary actor Bhanu Bandyopadhyay’s portrayal of a nurse in the 1967 film Miss Priyambada.

Kajal Chatterjee

Bollywood male actors have tried to entertain the audience in female costumes in several films. Some of them include:

1. Shashi Kapoor played a female role in Haseena Maan Jayegi.
2. Shammi Kapoor performed in a female role with charisma in the movie Bluffmaster in 1963.
3. Paresh Rawal, handled a female role very well in the film Tikku.
4. It was amazing to see ‘Comic King’ Govinda playing female roles in the movies Raja Babu and Aunty No. 1.
5. Aamir Khan’s performance as a female character in Baazi is truly praiseworthy.
6. Shahid Kapoor pulled off a female role quite well in Milenge Milenge with a short skirt, blonde hair and high heels.
7. Shreyas Talpade absolutely nailed it in a female avatar in Paying Guests and Golmaal 2.
8. It was really fun to see Akshay Kumar in a feminine look in the iconic film Khiladi (1992). He also did justice to the role of Laxmii (2020).
9. Versatile Rajpal Yadav’s role in the film Ardh, streamed on Zee5, won the hearts of audiences, all over again.

Sohini Raychaudhuri

Bhanu Bandyopadhyay’s performance as a woman was fun to watch in the Bengali movie Miss Priyambada (1967). In the film, he disguised himself as a lady nurse to gain entry to his friend’s girlfriend’s (Doli) house. His expressions were brilliant in every scene, especially when Doli’s uncle proposed to Priyambada. Wearing a sari, short hair, jewellery and a bindi on his forehead, his look was perfect for this hilarious film.

Sarbani Banerjee

I want to add the name of John Travolta in the 2007 movie Hairspray to the t2 list. In this modern musical remake of John Waters’ 1988 movie of the same name, Travolta very beautifully and convincingly portrayed the character of Edna Turnblad, Tracy’s loving mother.

Sourish Misra