Lopez's first big break came in 1997, when she was chosen to play the title role in Selena, a biopic of the Tejano pop singer Selena. Despite having previously worked with Nava on Mi Familia, Lopez was subjected to an intense auditioning process before landing the lead role of Selena. She earned widespread praise for her performance, including a Golden Globe Award for "Best Actress - Motion Picture Musical or Comedy". Later that year Lopez appeared in two major films. She starred in the horror film Anaconda alongside Ice Cube and Jon Voight, playing the role of Terri Flores, a director who is shooting a documentary while traveling through the Amazon River. Though, despite being a modest box office hit, the film was critically panned. Lopez then starred as the leading actress in the neo-noir film U Turn, which is based on the book Stray Dogs, starring alongside Sean Penn and Billy Bob Thornton.
In 1998, she had one of her most acclaimed roles, starring opposite George Clooney in Out of Sight, Steven Soderbergh's adaptation the Elmore Leonard novel. Cast as a deputy federal marshal who falls for a charming criminal, Lopez won raves for her tough performance and in the process she became the highest paid Latina actress in Hollywood history. That same year, she provided the voice for Azteca on the computer-animated film Antz. Lopez then starred opposite Vince Vaughn, in the psychological thriller film The Cell. She portrayed Catherine Deane, a child psychologist who uses a virtual reality to enter into the minds of her patients to coax them from their comas. The film was released on August 18, 2000 and became a box office success opening at number one. The following year, Lopez took a hiatus from acting in films to work on her music career.
In 2001, Lopez starred alongside Matthew McConaughey in the romantic comedy The Wedding Planner. The film debuted at number one, making her the first actress and singer in history to have a film and an album, J.Lo, at number one in the same week. Her next role in the supernatural romance Angel Eyes (2001), and in the psychological revenge thriller Enough (2002), both failed to click with audiences and critics alike. She appeared alongside Ralph Fiennes in the romantic comedy film Maid in Manhattan (2002). Her character, Marisa Ventura, is a struggling single mother who lives in the Bronx and makes her living cleaning rooms in a super-luxurious Manhattan hotel, who gets mistaken for a socialite by a princely politician. Maid in Manhattan was a box office hit opening at number one. The New York Times compared the films storyline to her 2002 song, "Jenny from the Block", commenting, "In her new single, Jenny From the Block, Jennifer Lopez declares that despite her enormous wealth and global fame, she has not lost touch with her roots."
Some of her other critically-acclaimed films include An Unfinished Life and Shall We Dance?. Two independent films produced by Lopez were well-received at film festivals: El Cantante at the Toronto International Film Festival, and Bordertown at the Brussels film festival. Her modestly successful film includes Monster-in-Law (2005). Gigli, however, would be a critical and commercial disappointment. In August 2007, Lopez collaborated on the feature film, El Cantante, with her husband singer-actor Marc Anthony. The film is in English, with a creative use of subtitles for songs with Spanish lyrics. In addition, she will appear in the romantic comedy The Back-Up Plan.