Why Madonna’s 1987 Screwball Comedy Was a Box-Office Bomb but a Touring Triumph

Why Madonna’s 1987 Screwball Comedy Was a Box-Office Bomb but a Touring Triumph
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In short: When Madonna pivoted from her successful music career to star in the 1987 comedy Who's That Girl, she expected a hit. Instead, the film became a notorious box-office failure. Yet, while critics savaged the movie, the accompanying world tour and soundtrack became massive, record-breaking successes that defined her cultural dominance.

Following the critical and commercial failure of her 1986 film Shanghai Surprise, Madonna sought redemption in a screwball comedy originally titled Slammer. She fought hard to convince Warner Bros. and producers to cast her as Nikki Finn, a street-smart woman framed for murder. She insisted on bringing in her friend James Foley to direct, despite his limited experience with major feature films. Production was plagued by delays, including a December 1986 halt due to heavy snowfall in New York, which Madonna used to work on the film's soundtrack and her upcoming tour.

Upon its August 7, 1987 release, the film was a disaster. It grossed only $2.5 million in its opening week and finished with a domestic total of about $7.3 million against a budget of up to $20 million. Critics were harsh, with some calling the film 'unbearable' and 'outrageously inept.' It earned five Golden Raspberry Award nominations, with Madonna winning Worst Actress. Observers, including biographer Andrew Morton, noted that the combination of a first-time director and a star struggling to find her footing in cinema failed to resonate with American audiences.

However, the project’s failure was strictly cinematic. The soundtrack sold over six million copies worldwide, and the title track became Madonna's sixth number-one single on the Billboard Hot 100. Simultaneously, the Who's That Girl World Tour—her first—grossed $25 million and played to 1.5 million people. Madonna later suggested that the film’s poor performance in the United States was partly because she 'upstaged' it with her tour, leading to audience confusion. While the movie faded, the music solidified her status as a global icon, proving that even a 'flop' could be part of a larger, unstoppable ascent.

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