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Director Nancy Meyers wrote the film with Nicholson in mind. "I haven't really seen him fall in love onscreen," says Meyers. "It was that part I wanted to see. I wanted to see Jack Nicholson fall in love with a middle-aged woman." At first blush, it feels like a piece of grotesque miscasting. After all, this is a man whose last serious girlfriend was Lara Flynn Boyle, a woman 33 years his junior. This is a man who has four children by three actresses, none of whom he is currently married to, and whose house sits on a hill near Marlon Brando's and Warren Beatty's. "I kind of squirm under sentiment," Nicholson admits, and he squirms visibly as he says it. "I've always been kind of a wisecracker and a deflector."
Granted, yes, it's totally unfair to saddle the character with the sins of an actor. It's something Nicholson has been dealing with his whole life--in part, as he's not slow to point out, because of the way his disarming ease onscreen fools audiences into thinking he's not acting at all. "It's a double-edged sword," he says. "They always say it's just like me. Always. And that's the best compliment. It's the most subtle compliment. When an audience says, 'Oooh, that's Jack, that's what he's really like,' you don't really want to hear it, but you've succeeded." Keaton--who has known Nicholson for more than 20 years, since they worked together in Reds--is more vehement in his defense. "Philosophically it's very different from many of the movies that he's been in," she says, "by nature of the fact that he's dating a woman who is his contemporary, which he may not do in his life, but who cares about his life? And I hope he has a great one, and if he dates a 25-year-old, it's not my business."
But a movie audience is like an unsequestered jury: How much can you reasonably expect it to set aside? Harry tells Erica, "I have never lied to you." Are those words he has ever, in fact, uttered in real life? The answer is classically Nicholsonian in its complexity. "I'll tell you the times I've said it," he explains carefully. "It would be a time, perhaps, when I'm with a serious girlfriend, at a time when I'm also in a relationship. Right? And I tell her--I've had this conversation more than once--'Look, I have the same kind of conflict about dissembling in a relationship that you do. It's not in the foreground with you, because that doesn't feel right, but don't think that I don't have this conflict. Therefore, I would never lie to you.' Not an attractive thing, but it's a very true thing from life." Got that? He's scrupulously honest--but only with the person he's cheating on somebody else with.