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She resumed her music career in 1998 with the widely successful duet with fellow R&B contemporary Monica, "The Boy Is Mine", which went on to become the best selling female duet of all time, and one of the longest running number one singles in history.
Her second album, Never Say Never, sold 16 million copies worldwide, featured two number one singles, and earned Norwood her first Grammy Award.
In 1996, her short-lived engagement on Thea led Norwood to star in her own show, the UPN-produced sitcom Moesha.
Appearing alongside William Allen Young and Sheryl Lee Ralph, she played the title role of Moesha Mitchell, a Los Angeles girl coping with a stepmother as well as the pressures and demands of becoming an adult.
In 2012 she became a series regular in the BET series The Game, and released her sixth album Two Eleven to critical praise.
In April 2015, Norwood made her Broadway debut in the musical Chicago.
Her work has earned her numerous awards and accolades, including a Grammy Award, one American Music Award, and seven Billboard Music Awards.
Never Say Never eventually became Norwood's biggest-selling album, selling over 16 million copies worldwide.
In the 2010s, Norwood received a critical and commercial resurgence.
In 2010, she returned to television as a contestant on the eleventh season of Dancing with the Stars and starred in the reality series Brandy & Ray J: A Family Business.
The album earned Norwood two Grammy Award nominations for Best New Artist and Best Female R&B Vocal Performance the following year, and won her four Soul Train Music Awards, two Billboard Awards, and the New York Children's Choice Award.
In 1996, Norwood also collaborated with Tamia, Chaka Khan, and Gladys Knight on the single "Missing You", released from the soundtrack of the F. The single won her a third Grammy nomination in the Best Pop Collaboration with Vocals category.