| 1 | Which movie sees Jack Lemmon and Tont Curtis dressed as women in an all girl band? Some Like It Hot |
| 2 | In which of Shakespeare’s plays does the character Viola pose as a boy, Cesario? Twelfth Night |
| 3 | Barry Humphries plays Dame Edna Everage, but which character does he plays as the "Australian Cultural Attache"? Sir Les Patterson |
| 4 | Who plays the killer in the 1960 film Psycho where he dresses in his mother’s clothes? Anthony Perkins |
| 5 | Which character in the TV series MASH dresses as a woman in an attempt to be dismissed from the army? Klinger |
| 6 | Which movie starred Michael Caine as a murderous transvestite psychiatrist? Dressed To Kill |
| 7 | Which 1970 hit for the Kinks was about a young man’s experience with a transvestite in a bar? Lola ("Well I’m not dumb but I can’t understand why she walked like a woman and talked like a man") |
| 8 | Which male actor played a female soap star in the film Tootsie? Dustin Hoffman. |
| 9 | Which British comedian describes himself as an "executive transvestite"? Eddie Izzard |
| 10 | The film Mrs Doubtfire, starring Robin Williams in the title role, was set in a Victorian property known as one of the "painted ladies". In which city is this tourist attraction? San Francisco |