Madonna’s Directing Dreams: When Ambition Outran Talent

When Madonna finally called time on her acting career, few in the industry shed a tear. Perhaps the only ones truly disappointed were the folks at the Razzies, who’d long relied on her to fill out their annual list of worst performances. With nine of those infamous trophies to her name, she’d become something of a regular. After her last live-action appearance in Die Another Day, and a voice role in Arthur and the Invisibles back in 2006, she quietly stepped away from the big screen.

But Madonna wasn’t quite done with the world of film. Instead of starring, she decided to try her hand at directing. Her first feature, Filth & Wisdom, which she co-wrote, was packed with ambition but struggled to find any real direction or spark. On the bright side, she managed to dodge nominations for Worst Picture and Worst Director at the Razzies, which, given her track record, was a minor victory.

Taking on WE: A Bigger Challenge Than Expected

Not one to back down, Madonna pressed on with her next project, WE. This time, she aimed for a sweeping historical drama. The film did manage to snag an Academy Award nomination for Best Costume Design and even picked up a Golden Globe for Best Original Song, thanks to her own track, ‘Masterpiece’. Still, these small wins couldn’t hide the fact that the film flopped at the box office, earning back less than a fifth of its budget and failing to impress critics or punters alike.

Initially, Madonna planned to write the script herself. It didn’t take long before she realised she was in over her head. She brought in Alek Keshishian, who’d previously directed her in Truth or Dare, to help shape the story. As she put it in an interview,

“I started writing it on my own, and then I realised that I needed help. It’s just too big a subject. I quite like the idea of collaborating in general. Not only is it lonely to do things on your own creatively, it’s also kind of arrogant. I guess some people are brilliant enough to be brilliant on their own and never doubt anything and come up with fabulous things.”

Collaboration Can’t Save a Sinking Ship

Even with a second writer on board, WE didn’t exactly set the world on fire. The film, with two credited screenwriters, still failed to deliver a compelling story. Madonna herself admitted she couldn’t wrangle the sprawling narrative into a workable script without help. It’s fair to reckon that if she’d gone it alone, the result might have been even messier.

After a string of lacklustre acting gigs, Madonna’s move behind the camera didn’t do much to change her fortunes. Both of her directorial efforts struggled to win over critics or audiences, and neither managed to shake her reputation for missing the mark in film. If she ever decides to direct her own biopic, it’s hard to imagine the outcome being much different.