While maintaining a recording career Norwood also gained fame for starring in several film and television productions, including popular UPN sitcom Moesha (1996-2001), a 1997 version of Rodgers and Hammerstein Cinderella and a supporting role in the 1998 horror sequel I Still Know What You Did Last Summer among others.
Norwood has sold over fourteen million albums worldwide. The RIAA ranks her as one of the best-selling female artists in American music history having sold 10.5 million albums.
Rodney "Darkchild" Jerkins consulted on the album Never Say Never, which was released on June 9, 1998 and became Brandy most successful album worldwide. Norwood co-wrote and produced six songs on the album which yielded her first number-one song on the U.S. Billboard Hot 100, "The Boy Is Mine", a duet with singer Monica. The song rose to one of the most successful records of the year, staying on top of the Billboard Hot 100 for thirteen weeks, and eventually garnered the pair a Grammy Award for "Best R&B Performance by a Duo or Group with Vocal". Critics rated Never Say Never highly, with All Music Guide Stephen Thomas Erlewine praising Brandy and her team for wisely finding "a middle ground between Mariah Carey and Mary J. Blige - it adult contemporary with a slight streetwise edge". Altogether the album spawned seven airplay and CD singles respectively, including Norwood second number-one song, Diane Warren written "Have You Ever".
By the following year, Norwood had entered a relationship with New York Knicks guard Quentin Richardson. The couple soon got engaged in July 2004 but Brandy eventually ended her 15-month engagement with the NBA player in October 2005. As reported, Norwood who had Richardson face tattooed on her back had to get the tatto transformed into a cat.
Returning from yet another musical hiatus, Brandy fourth album Afrodisiac was released on June 29, 2004 in North America, amidst both her weakest promotional blitz ever and the well-publicized termination of her short-lived business relationship with entertainment manager Benny Medina. Norwood ended her contract with his Los Angeles-based Handprint Entertainment after less than a year of representation following controversies surrounding Medina handling of the lead single "Talk About Our Love", and failed talks of a purported co-headlining tour with R&B singer Usher. Upon parting Norwood admitted her switch to Medina made her appreciate what she had with her mother, stating that "It was such a drastic change that it didn work for me. Nobody out there can match her passion for me."
Despite the negative blitz, Timbaland-produced Afrodisiac became Brandy most critically acclaimed album to date, with some citing the "more consistently mature and challenging" effect of Timbaland on Brandy music, and others calling it "very listenable and emotionally resonant", comparing it to "Janet Jackson at her best". Norwood described the CD as her most mature and versatile effort by then: "I just wanted to sing my heart out and connect with people. I was not old enough or mature enough before to get into people hearts. Now I am." Nevertheless Afrodisiac became the least successful album of Brandy career: While it debuted at number three on the Billboard 200, barely selling 500,000 copies domestically, the album widely failed to chart or sell noticeably outside the United States. "Talk About Our Love" reached number 6 in the UK but follow-up singles failed to obtain success on the pop charts.
In June 2006, Norwood was cast as one of three talent judges on the first season of America Got Talent, an amateur talent contest on NBC with executive producer Simon Cowell and host Regis Philbin. The broadcast was one of the most-watched programmes of the summer, and concluded on August 17, 2006 with the win of 11-year-old singer Bianca Ryan. Brandy was originally scheduled to return for a second season of the show in summer 2007, but eventually decided to step down following her recent legal woes, feeling that "she couldn give the new season the attention and commitment it deserved." She was replaced by U.S. reality TV star Sharon Osbourne.
In 1993 while recording her debut album, Brandy landed the role of Danesha Turrell in the ABC sitcom Thea, playing the 12-year-old daughter of protagonist Thea Turrell (Thea Vidale). The series was taken off the screens eight months after its release but earned her a Young Artist Award nomination for "Outstanding Youth Ensemble in a Television Series."
A year after Brandy made her big screen debut after winning the supporting role of sassy Karla Wilson in the franchise-flick I Still Know What You Did Last Summer. The movie outperformed the original with a total of 16.5 million at its opening weekend but critical reaction towards the film was largely disappointing, with film review site Rotten Tomatoes calculating a poor rating of 7% based on 46 reviews. Norwood, however, earned positive reviews for her "bouncy" performance which garnered her both Blockbuster Entertainment Award and MTV Movie Award nominations for "Best Actress" and "Best Breakthrough Female Performance" respectively. In 1999, she co-starred with Diana Ross in the telefilm drama Double Platinum.