The primary task went to makeup department head Ann Pala, hair department head Thomas Real, and costume designer Ellen Lutter.
In the film, Jack (Sandler) was living an almost perfect life, with the exception of one, annoying constant – his twin sister Jill (also played by Sandler). Every year he has to tolerate a Thanksgiving visit from his smothering sister, who doesn’t take long to turn his life upside down.
Pala and Real went through dozens of hair styles, textures, colors, and lengths (short, curly, and long), various nail colors and lengths, lip colors, skin tones, lashes, and teeth, all in different combinations. Working with three Sandler look-alikes, they created a number of different options for the filmmakers to choose from.
“Adam had played a girl in various sketches on ‘Saturday Night Live,’” says Pala, indicating that they had some idea of what might work with the actor. “The key factors in giving him feminine features were his eyes, cheeks, teeth, and bangs. We used nine different makeup skin tones to highlight and conceal.”
It was key to the filmmakers to try to create a real character in Jill. “Adam’s not playing a man playing a woman; he’s playing a woman,” notes Lutter. “It wasn’t a question of drag – we wanted to create a real woman, with specific features, character traits – it had to be genuine and natural. On the other hand, we were able to have a little fun because part of the character is that she looks exactly like her brother. We had the room to play and have some fun with Adam’s muscles and masculine demeanor – Jill is not a hyper-feminine character.”
Lutter says that when it came to Jill’s clothes, “Adam likes to be very comfortable, but being comfortable has nothing to do with being a woman. We tapped into the lightness of the character – and that’s where we had all our fun. Adam would always say, ‘I know you guys like Jill better,’ and it was true!”
Still, dressing Sandler as Jill wasn’t as simple as putting him in a dress. “Everything had to be manipulated – whether it was adding a detail around the neckline, or something with the arms, or working with the waist to build some hips. Everything had to be altered and adjusted to play with the proportions. It’s not like the clothes were just hanging around.”
Opening across the Philippines on Feb. 22, “Jack and Jill” is distributed by Columbia Pictures, local office of Sony Pictures Releasing International.