21 Iconic Gender-Swapping Performances (8 of 11)

14. Adam Sandler — Jack and Jill

In this 2011 comedy flick, Adam Sandler takes on the dual role of Jack, a successful advertising executive, and his loud, quirky twin sister, Jill. Sandler fully embraces the over-the-top humor of playing both siblings, using exaggerated physical comedy and mannerisms to distinguish between the two characters. While the film leans heavily into slapstick and absurdity, Sandler’s commitment to the dual roles is evident, creating a dynamic, albeit chaotic, interplay between the contrasting personalities of Jack and Jill.

15. John Travolta — Hairspray

John Travolta’s performance in Hairspray is an unexpected departure from his typical roles. He plays Edna Turnblad, a plus-sized mother who becomes a local celebrity while fighting for racial integration in 1960s Baltimore. Travolta is both hilarious and heartwarming, as he effortlessly encapsulates Edna’s infectious optimism and determination.