Jess used to be a man. Then he found himself in a female body. It wasn't funny. Why would anyone even think it was?
There's a scene in Tootsie (1982) that is surely one of the most unacclaimed scenes of all time: Dustin Hoffman's character, Michael, as 'Dorothy', makes a suggestion on the set, and the director dismisses it out of hand. As I remember it, Hoffman's face-conveying surprise, confusion, indignation-shows perfectly Michael's reaction to the absence of (and, just maybe, awareness of) male privilege. The entire movie should've been about that. Just that. It wasn't. And so I wrote Jess.