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In 1998, Lopez starred alongside George Clooney in the crime film Out of Sight (1998). Later that year, Lopez starred as Terri Chavez in the film Anaconda, which garnered negative reviews from critics despite being a box office success.
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The film was a commercial and critical success and is often cited by critics as her breakout role. Lopez received her first leading role in the Selena biopic of the same name in 1997. Her next two film roles in Jack (1996) and Blood and Wine (1997) were received similarly however, critics were divided by the latter. The film faced negative reviews and is considered to be a box office bomb. Lopez's first major film role came in the 1995 motion picture Money Train, alongside Wesley Snipes and Woody Harrelson. Second Chances and Hotel Malibu ran for only a brief period, receiving negative reviews.
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Following her departure from the show in 1993, Lopez made two guest appearances in the television series South Central, appeared in the made-for-television movie Lost in the Wild (1993) and starred as Melinda Lopez in the television series Second Chances (1993) and its spin-off Hotel Malibu (1994). From there, she received her first high-profile job in 1992 as a Fly Girl dancer on the television comedy program In Living Color. Lopez made her acting debut at age 16 with a small role in the 1986 film My Little Girl. She is also the richest actress in Hollywood, with an estimated net worth of $400 million (as of 2020). She is one of the highest-paid actresses in Hollywood and is the highest-paid actress of Latin descent, making up to US$20 million per film role. Jennifer Lopez has appeared in many motion pictures and television programs. Lopez attending the premiere of Hustlers at the 2019 Toronto International Film Festival.