When Breathless Mahoney first appears on-screen in Dick Tracy, you almost get the sense that Billy Wilder affixed Madonna with a cheap blonde wig to accentuate her “sleazy phoniness.” After all, it’s how Wilder styled Barbara Stanwyck in Double Indemnity, to give his noir femme fatale an air of honeysuckle-drenched murder. When Stanwyck was cast as Phyllis Dietrichson, she initially balked at playing someone so wicked after years of portraying heroines. It wasn’t until director Wilder asked her, “Well, are you a mouse or an actress?” that she agreed to star in a role that would leave a permanent mark on Hollywood. Stanwyck’s DNA is all over Madonna’s turn as Breathless, and in honor of the star’s 58th birthday (August 16), we’re returning to the look that declared her pop music’s femme fatale.

Much like Stanwyck transformed herself into the iciest blonde to never grace a Hitchcock film, one of Madonna’s greatest makeovers occurred in 1990’s Dick Tracy. She’d previously been in the spotlight in 1985 and 1987 with the Virgin tour and the Who’s That Girl world tour, but the albums she toured with showcased Madonna in her Downtown New York guise. She was fun, flirty, wore a shit-ton of costume jewelry, and all she wanted to do was dress you up in her love or cause a commotion. She was two years away from her controversial Erotica album in 1990, and she was still the girl next door — albeit more of a Mary Jane than a Gwen Stacy.

Madonna’s turn as Breathless Mahoney almost didn’t happen, but not for her own efforts. At the time, she was in a relationship with Warren Beatty and insisted on having the role, but she hadn’t exactly proven herself as a bankable actress after successive flops Shanghai Surprise and Who’s That Girl. But she was determined to make herself into a movie star. While Beatty earned $9 million for his role as Dick, Madonna worked for scale and earned only $1,440 a week. In turn, she also promoted the film herself by performing “Now I’m Following You” on her 1990 Blond Ambition tour. Madonna was determined to make Dick Tracy a hit and, consequently, her role as Breathless a star turn.

Madonna’s penchant for bawdy humor and double entendres was borne out of her Dick Tracy transformation. Her previous songs were straight to the point with regards to sex, like 1983’s “Physical Attraction”: “You say you want to stay the night / But you’ll leave me tomorrow, I don't care / All of your moves are right / We can take it anywhere / This physical attraction.” But by 1990, she had more of a theatrical approach to sex. Before she brought her Dick Tracy look-alike on stage, she introduced him with, “You know, a lot of people, they say I have a lot of balls. But you know what? They’re wrong. ’Cause what I have … is a Dick.” It’s the kind of lyric that would fly in a noir, where rapid wordplay is foreplay. It’s why her collaboration with Stephen Sondheim on the soundtrack album I’m Breathless is what truly made Breathless come alive.

On songs like “More” and “What Can You Lose,” Madonna shed the girl next door’s denim jackets for silk satin dresses and a deep, husky chainsmoker’s voice. She even smoked cigarettes while recording to get that of-the-era voice like Stanwyck.

Dick Tracy would go on to win several Academy Awards. Appearing with Michael Jackson as her date and dressed like a sultry mix of Phyllis Dietrichson and Harlow Jean, Madonna performed “Sooner or Later” and snagged the Best Original Song award for it. From that moment, she was a woman transformed. The poster for the Blond Ambition tour was a classic boudoir photo, showing a nearly naked Madonna curled up on a bed, her back facing the camera, with a come-hither glance over her shoulder. Gone were the earthy, free-love vibes of “Express Yourself” and “Like a Prayer.” She was now a woman who would kill to get her man — and then kill him when she was finished with him. “Give me that gun,” Madonna snaps at her lover on “He’s a Man,” the opening track to I’m Breathless. She’s been firing it at pop music ever since.