Naomi Watts’ Jean Holloway, a therapist, mother and wife, is struggling to reject the suburban stereotype. She and her husband Michael, portrayed by the ever charming Billy Cudrup who stole all our gypsy hearts in Cameron Crowe’s Almost Famous, are the cool, progressive parents, raising a daughter who says she’s not really a girl. But surburbia, however they despise it, is their world — and coming to terms with that causes Jean to dangerously spiral into delusion, eventually leading a double life.
Watt’s ethereal beauty, at once off-beat and elegant, makes her the perfect Jean — once free-spirited, now bound to routine. She won’t do it; she’s so perfect and intelligent, you’ll think, every time she gets herself into trouble, while Stevie Nicks calmly croons in the background. Cudrup, the steadfastly faithful and understanding husband, matches Watts’ charm. He’s too handsome; he’ll cheat one day, you’ll think, every time he tries his hardest to dodge the advances of his hot assistant. But their marital instability isn’t what makes Gypsy the psychological thriller that it is.
Gypsy, through Jean, sees life with an openness to ambiguity — one that has been repressed by authority figures in her life: her tenacious mother, the law, society, reason. As a therapist, she becomes too involved in her patient’s lives, too invested in their realities, that she begins to immerse herself, quite literally, in them, posing as a random person on the street, a fan at a coffee shop, a nice lady getting a blowout at the salon.
She takes a special interest in her patient Sam, who is devastated after her girlfriend Sidney breaks up with him. Looking out for Sam, she investigates Sidney, tries to see what he sees in her, why he can’t let go, what is so darn alluring — and finds herself growing attached. This breaks the dam and causes her to completely unravel, invading her patients’ private lives, their homes, taking pills, nursing a drinking habit, and contemplating on cheating on her husband. It all gets very messy and you can’t look away.
However faulty the story’s heroine is, you find yourself rooting for her, condoning her actions, even apologizing for them. In one episode, she is in Sidney’s apartment, and Michael is away on a business trip with his secretary, Lexi. Both on the brink of consummating extra marital desires, it’s odd how you find yourself wanting Jean to go and just do it, and hoping and praying that Michael doesn’t. Gypsy traps you into seeing your own biases — I wanted Jean to be her true self, knowing full well that “true self” is a lying, cheating sociopath. But I wanted Michael to remain pure, an ideal, a pillar of strength and reason, a moral anchor for Jean.
Though you’ll find yourself hating Jean, you’ll also be captivated. Interested. Her life is so perfect, why is she ruining it? On the other hand, you’ll get it. Her life is so ideal, everything is in place, everything is scheduled, planned and executed to perfection. Ruin it. A song featured in the show, Cindy Lauper’s cover of The Animal’s Don’t Let Me Be Misunderstood sums it up: I’m just a soul who’s intentions are good / Oh Lord, please don’t let me be misunderstood. If you think you’re doing the right thing, does it make you right? Gypsy says “Hell, yes!” Thank God it’s only TV.