SINCE TIME IMMEMORIAL, pop stars have tried to cross the rickety bridge from the music world to Hollywood. The scant few that make it to the other side are rightfully revered for taking the artifice of the stage and translating it to film. The rest fall through the cracks or are still clinging on for dear life, hoping for that one role that will shove them across.

Madonna is an unusual case. To stretch this metaphor out even further, she's made it across that bridge, bringing her charisma, sex appeal, and attitude to films like Desperately Seeking Susan, Evita, and A League of Their Own. But her outsized ego insists that she keep trying to make the journey, resulting in a filmography that is littered with woeful acting, worse box office returns, strange cameos in prestige pictures, and lots and lots of bare skin.

As with most of the artistic decisions she's made throughout her career, Madge's choice of projects seem to strain under the weight of her ego and her desire for respectability. This is how she attached herself to a knuckleheaded comedy like Who's That Girl, the horrific melodrama of The Next Best Thing, and the disjointed Damon Runyon adaptation Bloodhounds of Broadway. She has also let her heart be her guide, starring in the notoriously bad Shanghai Surprise, stinking up the otherwise dynamic Dick Tracy, and agreeing to star in a pitiful remake of Swept Away, just to be close to the man in her life at the time (Sean Penn, Warren Beatty, and Guy Ritchie, respectively).

What Madonna has never seemed to realize is that she only ever succeeds on the silver screen when she's playing some version of herself. When Desperately Seeking Susan was filmed, she was the titular Susan, all mesh tank tops and Wayfarers as she sashayed through the Lower East Side. She flexed her working-class muscles to portray a tough-as-nails female baseball player in A League of Their Own. And there's no way in Evita that she could have missed the correlation between playing the adored first lady of Argentina and being an arena-pop superstar. Naturally, then, Madonna's best onscreen work is when she reveals her behind-the-scenes self in the 1991 documentary Truth or Dare.

The trouble with Madonna nowadays is that every cinematic move she makes appears as calculated and rehearsed as her live performances. She leaves nothing to chance, which may be good for her celebrity but it's bad for an acting career. Try as she might, Madonna may never be herself on film again.