Bruno Mars
Saturday Night Live often sees pop stars branching out into comedy. With predictably hilarious results. Two minutes into this clip – a spoof of one of those Christians-to-the-lions talk shows – Bruno Mars comes on dressed as Crystal, the teenage daughter at odds with her mother. Mirth ensues.
Robbie Williams
The promo for Robbie’s 2011 single opens with Robbie delivering a straight-faced interview while clad in a black bobbed wig and a plunging dress. It soon becomes apparent he’s playing himself, but as someone whose offstage persona is as a transvestite. It’s oddly moving.
Queen
Arguably the most famous cross-dressing clip of all time, features Freddie Mercury in mini-skirt, wig (and moustache), Roger Taylor as a schoolgirl, Brian Deacon as an old lady and Brian May as a housewife in rollers. Popular legend holds that this video killed Queen’s career in the US. However, the single did go gold there, and Queen were hardly a hitmaking machine in the States anyway.
Katy Perry
In which the star dresses up as a 70s-style game show host. Do not expect to laugh.
Eminem
Just shy of two minutes in, Eminem is imagining being forced to attend the Grammys, “so you can sit me here, next to Britney Spears”. And, lo, there he is, dressed as Britney, and doing a rather good job of it. Britney escaped better than Christina Aguilera, who is portrayed by a blow-up doll, while Fred Durst and Carson Daly get to play themselves.
Miley Cyrus
Miley Cyrus dressed as Justin Bieber is a startling piece of reimagining. Startling in that she still looks like Miley Cyrus and Miley Cyrus alone. See Katy Perry and Bruno Mars for number of laughs delivered.