1. It showed me that I was NOT destined to marry a hot tub salesman named Gary. Even though I was a tween when the movie was released, Rosanna Arquette’s turn as melancholic housewife Roberta revealed what I suspected a life in the suburbs might mean for me. I began plotting my escape from the clutches of my hometown on Long Island right away.
2. The set took my obsession with Greenwich Village to a brand new level. I was already intrigued by the Village thanks to my hippie parents, who had played Dylan’s “Positively 4th Street” over and over during my formative years. But as I watched quirky, gypsy-bohemian Susan traipse around underground East Village clubs clad in black lace, I was instantly smitten with a whole new subculture. I was still too young to go clubbing, but this was the moment I decided I would live downtown—and I still do.
3. I found a role model in Susan, who refused to be slut-shamed. As Susan, Madonna beautifully and brutally smashed the madonna-whore complex to smithereens. She was splendidly sexual on her own terms, but unlike almost every single other female character who dared to have sex (and like it), she was not punished for her promiscuity. All hail this rare, positive example of female sexuality in a zany rom-com.
4. I saw a vision of swoon-worthy true love with Dez. Dreamy Aidan Quinn as loft-living, cat-loving Dez was the character that launched a thousand musician/actor hybrid boyfriends into my life, for better or worse. OK, mostly worse.
5. Oh, and did I mention the clothes? This film gave me permission to become the sartorial freak I secretly longed to be. (Oh, those BOOTS. That JACKET.) I suspected that my fashion sense was cutting edge, but I was still wearing Guess Jeans and Seven Stars sneakers like the rest of my 8th grade class. Thus began my addiction to vintage shopping. Madonna’s glorious, utterly original punk ensembles helped me to break free and find my own style.