The film was a box-office success and established a dynamic with Sandler — who was, at that point, one of the more bankable comic presences in Hollywood — that would be productive for both of them over the following years. More broadly, it established that Drew Barrymore was not simply a former child star who had survived; she was a current adult actress with commercial appeal and the ability to anchor mainstream entertainment.
Ever After (1998) followed, a revisionist Cinderella adaptation that gave her the opportunity to play a character of genuine substance and intelligence in a period setting. The film received positive reviews and expanded her audience. Roger Ebert, who was consistently one of the more perceptive critics of her adult career, noted that she had the ability to hold the screen and make viewers invested in her characters — qualities that are not as common as the industry sometimes pretends.
Never Been Kissed (1999) was the first Flower Films production on which Drew also served as executive producer. It grossed $84.5 million worldwide and confirmed that her production company was not simply a vanity project but a functional operation capable of identifying, developing, and delivering commercially successful films. The combination of acting and producing — of being both the face of the work and one of the people responsible for making it exist — was the model she would pursue for the next several decades.
Charlie’s Angels (2000) was the confirmation. A major studio action-comedy based on the 1970s television series, it required a star who could carry action sequences, comedy, and a certain amount of knowing self-awareness about the genre conventions it was operating within. Drew Barrymore, as producer and co-star, delivered all of those things. The film made over $264 million worldwide. Its sequel, Charlie’s Angels: Full Throttle (2003), added another $200 million. By any measure, these were hits — the kind of results that, in Hollywood’s accounting, translate directly into power.