Madonna’s Directorial Ambitions: The Movie She Couldn’t Save
Madonna left acting behind to try her hand at directing, but her films struggled with critics and audiences alike. Even after seeking help for her second feature, WE, the pop icon couldn’t turn things around.
When Madonna decided to step away from acting, few in Hollywood mourned the loss—except maybe the folks at the Razzies, who could always count on her to fill out their annual list of worst performances. With nine Razzie wins under her belt, the pop superstar had become a reliable fixture for the parody awards. After her last live-action appearance in Die Another Day and a voice role in 2006’s Arthur and the Invisibles, she quietly exited the acting scene for good.
But Madonna wasn’t finished with the movie business. Instead, she shifted her focus behind the camera, hoping to make her mark as a director. Her first feature, Filth & Wisdom, which she also co-wrote, was packed with ambition but lacked the clarity and skill needed to win over critics. On the bright side, she managed to dodge nominations for Worst Picture and Worst Director at the Razzies, a small victory in an otherwise rocky debut.
Taking on WE: A Bigger Challenge
Undaunted by her first film ’s reception, Madonna set her sights on a more ambitious project: the historical drama WE. She soon realized she was in over her head. The film did manage to snag an Academy Award nomination for Best Costume Design and even took home a Golden Globe for Best Original Song, thanks to her track “Masterpiece.” Still, these accolades couldn’t mask the fact that WE flopped at the box office, earning back less than a fifth of its budget and failing to win over critics.
Madonna initially planned to write the screenplay herself, but the scope of the story proved overwhelming. She brought in Alek Keshishian, who had directed her in Truth or Dare, to help shape the script. As she explained 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 and Creative Struggles
Even with a co-writer on board, the film struggled to find its footing. The script, credited to both Madonna and Keshishian, failed to bring coherence to the sprawling narrative. Madonna herself admitted she couldn’t condense the story into a workable script without help, and the final product reflected those challenges. The movie’s critical and commercial failure suggested that, despite her best efforts, she hadn’t found her stride as a filmmaker.
After two back-to-back disappointments, Madonna’s transition from acting to directing didn’t deliver the creative redemption she might have hoped for. With both films falling flat, the prospect of her directing her own biopic remains uncertain—and, for many, a questionable idea from the start.