1.Jessica Lange secures a lead role
Before director Sydney Pollack had come on board, Dustin Hoffman had interviewed more than a hundred actresses for the part of Julie, soap opera co-star and love interest of Dorothy/Michael. Pollack wanted Jessica Lange for the part, and she eventually got it. "The role [of Julie] required that you understand immediately why he's in love with her," Pollack said. "There was never a question why anyone was in love with Marilyn Monroe. She walked in a room and the guy would go – " Pollack made a face "if he had just seen Marilyn Monroe for the first time." "And you shot a close up of him and the audience said, 'That's it, they're in love.' Well, it saves you pages... Jessica Lange had it for me, in 'King Kong' of all things. I made a mental note: There's a movie star."
Makeup for Dorothy
The makeup testing process to perfect the look of Dorothy Michaels was endless, and no one was more relentless about it than Hoffman. "The first thing I said is that we have to do a bunch of make-up tests until we arrive at myself looking like a woman," he said. "Let's see if I can look really believable, not camp, not uglified, not denigrated... Because if I were a woman, I'd want to look as attractive as possible."
Identifying with the movie's themes
Hoffman said during the film's production that he felt like he knew Dorothy, his alter ego, and women identified with her, too. Costumer Jennifer Nichols watched one scene in which Dorothy, frustrated at being called pet names like "Tootsie" and "sweetie" by the director, blows up at him. "Now Alan is always Alan," she says. "Tom's always Tom and John's always John. I have a name, too. It's Dorothy." Nichols told Hoffman afterwards, "Oh, Dusty, that's it, that's just what we go through, that's just how we feel."
Sydney Pollack's interest in everything
Director Pollack knew a lot about every aspect of the filmmaking process, and some crew members became frustrated when they felt like their territory was being infringed upon. Director of photography Owen Roizman said he started to joke with Pollack when the director started reading the meter for light, something a director never normally did and usually left to the crew. "He used to read the meter all the time, and he checked the contrasts in his viewing glass the same as the cameraman would do," Roizman said. "I would take the meter out and read the light... I'd tell the assistant cameraman what f/stop I was using and I'd give him an f/stop that was totally unbelievable for the amount of light that was on the set. And Sydney would say, 'How can you see at that f/stop?' And I said: 'Don't worry about it, Syd, I have a special way of doing it, it'll be fine.' And just before we'd go, the assistant cameraman would open up the f/stop we were really gonna use. And we'd go to dailies and, of course, the stuff looked fine."
Splurging on a coat
While Hoffman was still a struggling young actor, before he was cast in "The Graduate," he had a variety of jobs, including working at a counter at Macy's (once blaming a woman for shoplifting just to see what would happen), demonstrating toys for the holiday season, and holding down people who were getting electroshock therapy in a psychiatric institute. Another actor told him that if he ever wanted to get hired, he'd have to look more clean-cut, so Hoffman went out and bought a $150 coat after he'd gotten a check from a role on TV. "I had never spent so much money on myself before," Hoffman said. "I went to pay for it and I was trembling. Such luxury! When I walked out with the coat.... everything went black in front of me.... And I thought – I really did – 'I'm being punished.' What it was was the night of the big blackout."