Madonna pursued Hollywood because she viewed filmmaking as a natural extension of creating music videos and narrative stories, and because her fame gave her opportunities to take prominent roles. Although Desperately Seeking Susan, A League of Their Own and Evita received praise, several other films were criticised or commercially unsuccessful, reinforcing the view that her acting career never matched her musical achievements.

Madonna said her celebrity image made it difficult for audiences to separate her from the characters she played, creating an additional challenge on screen. However, the article argues that her biggest problem was a lack of self-awareness: musical success did not necessarily indicate acting ability, and continuing to accept unsuitable roles contributed to her record number of Golden Raspberry Awards.