Women have always been underrepresented in movies and not until recently has the representation of women in movies improved. To investigate the improvement of female representation and its relationship with a movie's success, we propose a new measure, the female cast ratio, and compare it to the commonly used Bechdel test result. We employ generalized linear regression with $L_1$ penalty and a Random Forest model to identify the predictors that influence female representation, and evaluate the relationship between female representation and a movie's success in three aspects: revenue/budget ratio, rating, and popularity. Three important findings in our study have highlighted the difficulties women in the film industry face both upstream and downstream. First, female filmmakers, especially female screenplay writers, are instrumental for movies to have better female representation, but the percentage of female filmmakers has been very low. Second, movies that have the potential to tell insightful stories about women are often provided with lower budgets, and this usually causes the films to in turn receive more criticism. Finally, the demand for better female representation from moviegoers has also not been strong enough to compel the film industry to change, as movies that have poor female representation can still be very popular and successful in the box office.