1 Madhubala in Raj Hath (1956)
Sohrab Modi's romantic fantasy Raj Hath (1956) concentrated on the tensions between two neighbouring kingdoms in Rajasthan when a wedding proposal between two goes awry. When things escalate to all-out war, Madhubala plays the gutsy princess who dons a male disguise to spy on the opposing kingdom.
2 I.S. Johar in Bewakoof (1960)
A complete I.S. Johar film (he wrote, produced and directed the feature), Kishore Kumar and Pran played half-brothers alleged 'switched' at birth. But the highlight of the film was Johar dressing up a woman to woo Mukhri and Ulhas in the song 'Dekh idhar dekh tera dhyaan kahaan hai', sung by Asha Bhonsle.
3 Kishore Kumar in Half Ticket (1962)
This adaptation of Jerry Lewis's You're Never Too Young (1955) has Kishore Kumar doubling up as male and female singers in the 'duet' 'Aake Seedhi Lagi Dil Pe' in Half Ticket. Kumar plays Vijay who is unknowingly used as a mule by Raja Babu, a drug smuggler played by Pran. This is regarded as one of the earliest instances of a mainstream actor dressing up in drag for a role, although this occurred fairly regularly in the early days of Indian cinema when women weren't permitted to act.
4 Shammi Kapoor in Bluff Master (1963)
In Manmohan Desai's Bluff Master (1963), Shammi Kapoor plays an irrepressible conman. He performs the memorable qawwali 'Oy Chali Chali Kaisi Hawa' in drag with his sidekick Mohan Choti. Accompanied onscreen by Saira Banu, the duet was sung by Shamshad Begum and Usha Mangeshkar and composed by Kalyanji-Anandji.
5 Mehmood in Arzoo (1965)
In the Sadhana-Rajendra Kumar romance, Arzoo (1965) set in Kashmir, Mehmood is Mamdu, a houseboat owner who practically urges the two youngsters to woo each and fall in love. As comic relief, he becomes a woman in order to obtain a house in Delhi for him and his fiancée.
6 Shashi Kapoor in Haseena Maan Jayengi (1968)
Prakash Mehra's directorial debut, Haseena Maan Jayengi (1968) featured Shashi Kapoor in a double role as the straightforward Kamal and duplicitious Rakesh, both who are trying to woo Babita's Archana. In the song 'Suno suno kanyaon ka varnan', he tries on different female avatars (from a Kashmiri girl to a jogan) in front of his fellow classmates.
7 Biswajit and Babita in Kismat (1969)
The popular song 'Kajra Mohabbat Wala' in the film was composed by O.P. Nayyar and sung by Asha Bhonsle and Shamshad Begum. Another Manmohan Desai production, the hit tune from Kismat (1969) was picturised on Biswajeet and Babita who both switched genders as they try to escape a terrorist gang. Biswajeet also dressed in drag for a scene in his previous film Biwi Aur Makaan (1966).
8 Tanuja in Do Chor (1972)
Tanuja starred opposite her mother Shobana Samarth in Padmanabh's Do Chor (1972). She played Sandhya, a con woman avenging her father's death and her mother's institutionalization. Dharmendra played a former thief Tony who aids Sandhya while she breaks into the houses of her adversaries disguised as a man.
9 Rishi Kapoor in Rafoo Chakkar (1975)
The grand tradition of Kapoor men in drag continued with Rishi Kapoor. In Rafoo Chakkar (1975), Kapoor and Paintal are the only witnesses to a murder and dress up as women to avoid being recognized. Inspired by the Tony Curtis-Jack Lemmon hit, Some Like It Hot (1959), Kapoor was paired opposite Neetu Singh, who later became his wife.
10 Amitabh Bachchan in Laawaris (1981)
Prakash Mehra's classic Laawaris with Amitabh Bachchan featured two versions of the popular hit 'Mere angne mein'. One version was sung by a young Alka Yagnik who received her first Filmfare nomination for it and the other by Bachchan. His enactment (in drag) of the different kinds of wives in the song is an all-time favourite for many
11 Sanjay Dutt in Mera Faisla (1984)
This lesser-known Sanjay Dutt film has him under disguise in the women's locker room in 'Allah meri laaj bacchana', sung by Mahesh Kumar. Co-starring Rati Agnihotri, Jayapradha and Pran, Dutt played a young man trying to become a police officer after his late father was labelled a traitor.
12 Sridevi in Mr. India (1987)
One of most memorable sequences in Shekhar Kapur's blockbuster Mr. India (1987) was of Sridevi mimicking Charlie Chaplin's Little Tramp. As investigative reporter Seema, Sridevi infiltrates a gambler's den and gets timely help by Mr. India himself.
13 Akshay Kumar in Khiladi (1992)
Akshay Kumar's big breakthrough came with the successful thriller Khiladi (1992). It led to Kumar starring in seven other films with 'Khiladi' in the title. He played an eternal prankster whose fake kidnapping scheme somehow becomes real. In the film's early funny sequences, Kumar poses as a woman along with co-star Deepak Tijori in order to woo co-eds.
14 Aamir Khan in Baazi (1995)
Before their successful collaboration in Lagaan (2001), Ashutosh Gowariker and Aamir Khan first came together as director-actor in Baazi (1995). Khan played Inspector Amar, a dedicated officer determined to get to the bottom of situation, even if it means frolicking as a club dancer in the song 'Dole dole dil dole'.
15 Kamal Haasan in Chachi 420 (1997)
Kamal Haasan's directorial debut, Chachi 420 (1997), was almost a direct lift of Robin Williams's Mrs. Doubtfire (1993). In the middle of a divorce and custody battle, Haasan becomes Mrs. Lakshmi Godbole, a nanny for his daughter, approved by both his father-in-law and soon-to-be ex-wife. Unfortunately, Mrs. Godbole gets involved in a few romantic entanglements that could very well be her undoing.
16 Govinda in Aunty No. 1 (1998)
Right on the heels of Kamal Haasan's Chachi came Govinda's Aunty No. 1 adapted from the Marathi play Moruchi Mavshi. Directed by Kirti Kumar, Aunty No. 1 had Govinda impersonating an foreign-return aunt to help out his friends. Like in Chachi 420, he too manages to find himself in the midst of an impossible love triangle.
17 Salman Khan in Jaan-e-mann (2006)
Shirish Kunder's first film as director was a big-scale romance set in New York and India. Salman Khan played Suhaan trying to set up his ex-wife Piya (Preity Zinta) with a former admirer Agastya played by Akshay Kumar. Suhaan goes to many lengths to ensure they get together, including beating up a gang of miscreants for Agastya in a bizarre sequence under disguise as a woman in a pink dress!
18 Rani Mukerji in Dil Bole Haddippa! (2009)
In Yash Raj Films' Dil Bole Haddippa!, Rani Mukerji is Veera, a village girl whose real ambition is to play cricket. Veera pretends to 'Veer' in order to be a part of the Aman Cup tournament against Pakistan. Fortunately for her, not many realize her grand deception until the big match day.
19 Vidya Balan in Bobby Jasoos (2014)
As Bilkis 'Bobb' Ahmed, Vidya Balan dons many different disguises, both male and female, as part of a private investigation to hunt down two missing girls. The aspiring detective relies more on chance and luck than actual spy work.
20 Saif Ali Khan, Riteish Deshmukh and Ram Kapoor in Humshakals (2014)
Humshakals is infamously referred to as the worst film in Indian history. It lives up to that honour by creating an improbable scenario in which Saif Ali Khan, Riteish Deshmukh and Ram Kapoor have doppelgängers and their doppelgängers have doppelgängers. To add insult to injury, writer-director Sajid Khan has the trio dress as up women in order to seduce their lookalikes.