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In 2019, Norwood was honored with the BMI President's Award at the BMI R&B/Hip-Hop Awards, organized by Broadcast Music, Inc. In June, she appeared on Canadian singer Daniel Caesar's sophomore album Case Study 01, lending vocals to their duet "Love Again". Released as a single through Golden Child Recordings, eOne Music and Norwood's new imprint, Brand Nu Inc., it earned them a Grammy Award nomination for Best R&B Performance at the 62nd awards ceremony and reached the top of the Billboard Adult R&B Songs chart, becoming Norwood's first song to do so. In September 2019, she released the buzz single "Freedom Rings" which was released to coincide with the 25th anniversary of her self-titled debut album. In May 2020, Norwood released “Baby Mama” as the lead single from her seventh studio album B7, set for release July 31, 2020. In an interview with Rated R&B, Brandy shared her vision for B7. "I wanted to reconnect with music and find my sound — that unique sound that I’ve been searching for," she said.

Brandy also names her father, vocal coach Willie Norwood, as instrumental to her discovery and development as a musician. She exclaims that her dad “taught me everything that I know [about singing]”. About her dad, Brandy states: “I grew up singing in church with my dad, where he was the musical director and we sang gospel songs in acapella almost exclusively. He bought me my first 4-track tape recorder. At first, I didn’t like my own voice, but he encouraged me to embrace the unique qualities of my voice.”

As of July 2018, she has sold over 40 million records worldwide, with over 8.62 million albums sold in the U.S., making her one of the best selling female artists of all time. The Recording Industry Association of America (RIAA) lists Norwood as one of the top-selling artists in the United States, with 10.5 million certified units in album sales. Her work has earned her numerous awards and accolades, including a Grammy Award, an American Music Award, and seven Billboard Music Awards. She has become known for her distinctive sound, characterized by her peculiar timbre, voice-layering, and intricate riffs, which has earned her the nickname "The Vocal Bible" from industry peers and critics.

In January 2017, Norwood competed with her brother Ray J on the FOX reality cooking series My Kitchen Rules. In July 2018, Norwood became a series regular on the Fox musical drama television series Star. She played the role of Cassie, starting as a recurring role in the second season, and remained a series regular until the series' ending in 2019. The same year, she appeared on "Optimistic", a Sounds of Blackness cover that preceded the self-titled debut of supergroup August Greene, consisting of Common, Robert Glasper and Karriem Riggins, as well as on Dutch DJ's Lucas & Steve's "I Could Be Wrong," a dance-heavy rework of her 1994 single "I Wanna Be Down" that became a minor hit on the dance charts.

Norwood has also made her impact in the film and television industry as well. Norwood was the first African American to play the role of Cinderella. Her role as Cinderella inspired many African American actors. Speaking on the role, Keke Palmer said "I feel like the reason I'm able to do this [becoming the first African American Cinderella on Broadway] is definitely because Brandy did it on TV". Norwood's TV-show Moesha on UPN was also one of the longest-running Black sitcoms of all time. On stage, Norwood made Broadway history along with co-star Lana Gordan by becoming the first black co-leads in Chicago the Musical in 2017.

In January 2016, Norwood starred as the lead in the BET sitcom Zoe Ever After, which she also co-created and co-executive produced. Filmed in Atlanta, Georgia, the multi-camera romantic comedy revolved around Zoe Moon, a newly single mom stepping out of the shadow of her famous boxer ex-husband, while trying to balance dating, motherhood, and a blossoming career in cosmetics. While it debuted to respectable ratings, Norwood decided not to return to the show, and it was soon after cancelled. The same month, Norwood unveiled "Beggin & Pleadin," a previously unreleased song, on SoundCloud. The unconventional record garnered strong reviews from industry experts, prompting her to officially release it as a digital single through her own label Slayana Records on January 21. That February, Norwood announced her Slayana World Tour, which highlighted stops in both Europe and Oceania. Her first headlining tour in eight years, it was ended ahead of schedule on June 30 after Norwood was hospitalized due to exhaustion. In March, Norwood sued Chameleon Entertainment Group and its president, Breyon Prescott, after the label reportedly refused to allow her to record and release new albums. In November, Norwood became the second recipient of the Lady of Soul Award at the Soul Train Music Awards. Her stripped-down nine-minute song medley was met with overwhelming praise.

After finishing the filming of the final season of The Game, Norwood made her Broadway debut in the musical Chicago, in which she played the lead role of Roxie Hart, beginning in April 2015. Although initially a six-week run, her engagement was extended until August 2015, prompting Norwood to reprise the role on several occasions in 2016 and 2017. Also in 2015, Norwood appeared on the 99 Souls mashup single "The Girl Is Mine", for which she re-recorded her vocals from "The Boy Is Mine." The song reached the top 10 in the United Kingdom and top 40 on other international charts, where it became her highest-charting single in years.

Since the start of her career, Brandy has named Whitney Houston as her most prominent music and entertainment influence. Early in her career, she would often describe Houston as her “idol”, crediting her voice, music, and performances as critical to her, both personally and professionally. In a 2014 interview, Brandy stated that, “as a professional musician, I would say that Whitney Houston is the greatest voice of all time.” She elaborates, saying “She was always the idea for me. I wanted to be like her, sing like her, and do everything she was doing.” Beginning in the late 1990s, Houston would evolve as a personal friend and mentor to Brandy, with Houston nicknaming herself as Norwood's “godmother”.

Afrodisiac has been credited as one of predecessors to the Alternative R&B subgenre. In a 2014 music and fashion conversation with NPR, singer and model Solange discussed the album, saying "Brandy is really the foundation of a lot of this very innovative, progressive, experimental R&B. Brandy really influenced a lot of that. Frank Ocean will say it. Miguel will say it." In an interview with MalcolmMusic, Miguel revealed that he was a "huge fan growing up", stating that Brandy had "killed it from the first album".

In March 2013, Norwood returned to film, joining an ensemble cast consisting of Jurnee Smollett-Bell, Lance Gross and Vanessa L. Williams in Tyler Perry's drama Temptation: Confessions of a Marriage Counselor. Norwood plays supporting character Melinda, a woman with secrets. The film received generally negative reviews from critics but became a moderate US box office success. In June 2013, Norwood signed with Creative Artists Agency, headquartered in Los Angeles, and in early 2014, she arranged a management deal with MBK Entertainment with CEO Jeff Robinson. In July, she was also inducted as an honorary member of Alpha Kappa Alpha sorority. The same month, Norwood released a cover version of Coldplay's song "Magic" to her TwitMusic account; it peaked at number one on Billboard' s Trending 140 chart. Also in 2014, Norwood made guest appearances on VH1's Love and Hip Hop: Hollywood and the TV Land sitcom The Soul Man. At the 2014 BET Hip Hop Awards, she reunited with Queen Latifah, MC Lyte, and Yo-Yo to perform the hip hop remix of "I Wanna Be Down" in celebration of its 20th anniversary.

In 2011, Norwood joined the cast of the BET comedy series The Game, playing the recurring role of Chardonnay, a bartender. She became a regular cast member by the next season. In February 2012, Norwood reteamed with Monica on "It All Belongs to Me", which was released as a single from the latter's album New Life. Norwood's own comeback single "Put It Down" featuring singer Chris Brown was released later that year. The song reached number three on Billboard' s Hot R&B/Hip-Hop Songs chart, becoming her first top ten entry in ten years. Her sixth album Two Eleven, which was released in October, saw a return to her R&B sound, but with what Norwood described a "progressive edge". A moderate commercial success, it was viewed as a humble comeback from Norwood, reaching number three on the US Billboard 200, and the top of the Billboard US Top R&B/Hip-Hop Albums chart.

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. 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. She starred in and executive produced a sitcom titled Zoe Ever After on BET which premiered in January 2016.

In April 2010, Norwood and Ray J debuted in the VH1 reality series Brandy and Ray J: A Family Business along with their parents. The show chronicled the backstage lives of both siblings, while taking on larger roles in their family's management and production company, R&B Productions. Executive produced by the Norwood family, the season concluded after eleven episodes, and was renewed for a second season, which began broadcasting in fall 2010. A Family Business, a compilation album with previously unreleased content from the entire cast was released on Saguaro Road Records in June 2011. Critics such as The Washington Post declared it an "awkward and adorable and really, really wholesome collection." While the album failed to chart, it produced three promotional singles, including the joint track "Talk to Me".

In fall 2010, Norwood appeared as a contestant on season 11 of the ABC reality show Dancing with the Stars, partnered with Maksim Chmerkovskiy. She ultimately placed fourth in the competition, which was a shock to the judges, viewers, studio audience, and other contestants that considered her one of the show's frontrunners throughout the entire competition. In August 2011, it was confirmed that Norwood had signed a joint record deal with RCA Records and producer Breyon Prescott's Chameleon Records. In September, a new talent show, Majors & Minors, created by musician Evan Bogart, premiered on The Hub. It followed a group of young performers age 10–16 and their chance to be mentored by some established artists such as Norwood, Ryan Tedder and Leona Lewis. Later that same year, Norwood returned to acting roles with recurring appearances on The CW's teen drama series 90210, and in the fourth season of the Lifetime's comedy series Drop Dead Diva, in which she played the role of Elisa Shayne.

In December 2009, she officially introduced her rapping alter-ego Bran'Nu with two credits on Timbaland's album Timbaland Presents Shock Value 2, and was cast in the pilot episode for the ABC series This Little Piggy, also starring Rebecca Creskoff and Kevin Rahm, which was recast the following year.

Norwood's fifth studio album, Human, was released in December 2008, produced by Toby Gad, Brian Kennedy, and RedOne. Distributed by Koch Records and Sony Music, the album marked Norwood's debut on the Epic Records label, and her reunion with long-time contributor and mentor Rodney Jerkins, who wrote and executive produced most of the album. Generally well received by critics, Human debuted at number fifteen on the U.S. Billboard 200 with opening week sales of 73,000 copies. With a domestic sales total of 214,000 copies, it failed to match the success of its predecessors. While lead-off single "Right Here (Departed)" scored Norwood her biggest chart success since 2002's "Full Moon", the album failed to impact elsewhere, resulting in lackluster sales in general and the end of her contract with the label, following the controversial appointment of Amanda Ghost as president of Epic Records, and Norwood's split with rapper Jay-Z's Roc Nation management.

In December 2007, Norwood's attorney Blair Berk stated that the Los Angeles City Attorney determined Norwood should not be charged with any "crime relating to the accident back in 2006." In May 2009, Norwood stated, "The whole experience did completely change my life, and I can say that I think I'm a better person from it. You know, I still don't understand all of it and why all of it happened, but I definitely have a heart, and my heart goes out to everyone involved. I pray about it every single day, and that's all I can really say on the subject."

Nevertheless, there have been multiple lawsuits filed against Norwood, all of which were ultimately settled out of court by her attorney Ed McPherson. Aboudihaj's parents filed a $50 million wrongful death lawsuit against Norwood. Filed on January 30, 2007, the lawsuit was initially set to go to trial in April 2009, but was eventually canceled as Norwood had settled out of court with Aboudihaj's parents. Aboudihaj's husband also filed a lawsuit against Norwood, suing her for an undisclosed amount of financial relief to cover medical and funeral expenses, as well as legal costs and other damages. He rejected his part of a $1.2 million settlement offer in February 2009, but did settle in November of that year. The couple's two children, who also filed a lawsuit against Norwood, received $300,000 each, according to court documents filed in L.A. County Superior Court on June 2, 2009. Two other drivers who were involved and injured in the accident also filed a lawsuit against Norwood. They settled with Norwood for undisclosed amounts.

In February 2006, Norwood began appearing in a recurring role on UPN sitcom One on One, playing the sister to brother Ray J's character D-Mack. In June, she was cast as one of three talent judges on the first season of America's Got Talent, an amateur talent contest on NBC executive-produced by Simon Cowell and hosted by Regis Philbin. The broadcast was one of the most-watched programs of the summer, and concluded on August 17, 2006 with the win of 11-year-old singer Bianca Ryan. Norwood was originally slated to return for a second season in summer 2007, but eventually decided not to, feeling that she "couldn't give the new season the attention and commitment it deserved," following the fatal 2006 car accident in which she was involved. She was replaced by reality TV star Sharon Osbourne.

Driving home on December 30, 2006, Norwood was involved in a fatal automobile collision on Los Angeles' 405 Freeway. Thirty-eight-year-old Awatef Aboudihaj was the driver of a Toyota that was struck by Norwood's Range Rover. Aboudihaj died from her injuries at the L.A. Holy Cross Hospital the following day.

Returning from yet another hiatus, Norwood's fourth album Afrodisiac was released in June 2004, amid 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's handling of the lead single "Talk About Our Love", and failed negotiations of a purported co-headlining tour with R&B singer Usher. Despite the negative publicity, Afrodisiac became Norwood's most critically acclaimed album, with some highlighting the "more consistently mature and challenging" effect of Timbaland on Norwood's music, and others calling it "listenable and emotionally resonant", comparing it to "Janet Jackson at her best." A moderate seller, the album debuted at number three on the Billboard 200, and received certifications in the United States, Europe and Japan. "Talk About Our Love" reached number six in the United Kingdom, but subsequent singles failed to score successfully on the popular music charts. Later that year, she guest-starred as Gladys Knight in the third-season premiere of American Dreams, in which she performed "I Heard It Through the Grapevine".

After eleven years with the company, Norwood asked for and received an unconditional release from Atlantic Records at the end of 2004, citing her wish "to move on" as the main reason for her decision. Completing her contract with the label, a compilation album titled The Best of Brandy was released in March 2005. Released without any promotional single, it reached the top 30 in Australia, the United Kingdom and the United States, where the collection was appreciated by contemporary critics who noted the creativity of Norwood's back catalogue. Andy Kellman of AllMusic expressed, "This set, unlike so many other anthologies from her contemporaries, hardly confirms dwindling creativity or popularity." Thereupon she reportedly began shopping a new record deal under the auspices of Knockout Entertainment, her brother's vanity label.

By the following year, Norwood had begun a relationship with NBA guard Quentin Richardson, who was then playing for the Los Angeles Clippers. The couple soon became engaged in July 2004 but Norwood eventually ended their 15-month engagement in October 2005. It was reported that Norwood had to get a tattoo of Richardson's face on her back transformed into a cat. In 2010, she briefly dated rapper Flo Rida. At the end of 2012, Norwood became engaged to music executive Ryan Press. In April 2014, Norwood called off her engagement with Press following their breakup earlier that year.

During the production of her album Full Moon in mid-2001, Norwood became romantically involved with producer Robert "Big Bert" Smith. The couple kept their relationship secret until February 2002, when Norwood announced that she was expecting her first child. However, a year after the birth of their daughter, Sy'rai Iman Smith, on June 16, 2002, an event tracked by the four-part MTV reality series Brandy: Special Delivery—Norwood and Smith separated. In 2004, Smith revealed that the pair had never been legally wed, but that they had pretended to marry to preserve Norwood's public image. Norwood later stated that she regarded her relationship with Smith as a "spiritual union and true commitment to each other."

After a lengthy hiatus following the end of Moesha, and a number of tabloid headlines discussing her long-term battle with dehydration, Norwood returned to music in 2001, when she and brother Ray-J were asked to record a cover version of Phil Collins' 1990 hit "Another Day in Paradise" for the tribute album Urban Renewal: A Tribute to Phil Collins. Released as the album's first single in Europe and Oceania, the song became an instant international success overseas, scoring top-ten entries on the majority of all charts it appeared on. Full Moon, Norwood's third studio album, was released in February 2002. It was composed of R&B and pop-oriented songs, many of them co-created with Jerkins, Warryn Campbell and Mike City. Its lead single "What About Us?" became a worldwide top-ten hit, and the album's title track was a Top 20 hit in the United States and the UK. Media reception was generally lukewarm, with Rolling Stone describing the album as "frantic, faceless, fake-sexy R&B." Within the coming year, Norwood and Robert "Big Bert" Smith began writing and producing for other artists such as Toni Braxton, Kelly Rowland, and Kiley Dean. Norwood's foray into reality television began in 2002 with the MTV series Diary Presents Brandy: Special Delivery; the show documented the final months of Norwood's pregnancy and the birth of her daughter Sy'rai.

Throughout the 2000s, Norwood held a precarious position in the pop industry. In 2002, she starred in the reality series Brandy: Special Delivery, documenting the birth of her daughter. Her third and fourth albums, Full Moon (2002) and Afrodisiac (2004), were released to critical and commercial success. She served as a judge on the first season of America's Got Talent before being involved in a widely publicized car accident in 2006. After several lawsuits stemming from the accident, Norwood's fifth album, Human (2008), was released to commercial failure.

Songwriter Sean Garrett credits the vocal work on the album Full Moon for his approach to writing, saying "I take a lot from what [Brandy] and Rodney did on the Full Moon album. I was extremely impressed with it and I always try to outdo that album". B.Slade spoke of the album, commenting Full Moon single-handedly changed the vocal game. "It has been the template for vocal choices and background vocal arrangements [for years]." R&B singer Melanie Fiona, especially admired the singer's work on that album. Neo soul singer India.Arie often cites the album, particularly the song "He Is" as being the template for a wide array of singers." The oft-praised vocal work on the album sparked the idea of Norwood gaining the subjective nickname the "vocal bible". Canadian R&B singer Keshia Chanté credited the album for inspiring her writing for her album Night & Day, while American singer Luke James referred to Full Moon as the "bible" of 2000s contemporary R&B, calling it the "blueprint of how to do vocals."

Norwood has had many endorsements in her career. In 1999, she became a CoverGirl, appearing in a number of commercials. She also represented the brands Candie's in 1998 and DKNY in the Spring of 2000. In the late 1990s Norwood was represented by Wilhelmina Agency, one of the leading modeling agencies in the industry. In 1999, Mattell released the Brandy Doll. The doll featured Norwood in a reddish orange blouse and orange long skirt. Next to this, the Holiday Brandy Doll was released in 2000 along with another "Brandy Doll". Millions of the dolls were sold and they were one of the biggest selling toys for Mattel. In 2005, Brandy became the spokesperson for Ultima, a company for hair weaves and wigs. As of 2014, she no longer represents them.

Fledgling producer Rodney "Darkchild" Jerkins was consulted to contribute to Norwood's second album Never Say Never, which was released in June 1998. 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 that has become the most successful song by a female duo in the music industry. Exploiting the media's presumption of a rivalry between the two young singers, the song was one of the most successful records in the United States of all time, spending a record-breaking thirteen weeks atop the Billboard charts, and eventually garnering the pair a Grammy Award for Best R&B Performance by a Duo or Group with Vocal. The album's success was equally widespread, and after extensive radio play of the single overseas, the label released it globally during the summer. Never Say Never eventually became Norwood's biggest-selling album, selling over 16 million copies worldwide. Critics rated the album highly, with AllMusic's Stephen Thomas Erlewine praising Norwood and her team for wisely finding "a middle ground between Mariah Carey and Mary J. Blige—it's adult contemporary with a slight streetwise edge." Altogether, the album spawned seven singles, including Norwood's second number-one song, the Diane Warren-penned "Have You Ever?" She also embarked on the successful Never Say Never World Tour in 1998, consisting of sold out performances in Europe, Asia, and the United States.

In 1997, Norwood was hand-picked by producer Whitney Houston to play the title character in Rodgers and Hammerstein’s television version of Cinderella featuring a multicultural cast that also included Jason Alexander, Whoopi Goldberg, and Houston. The two-hour Wonderful World of Disney special garnered an estimated 60 million viewers, giving the network its highest ratings in the time period in 16 years, and won an Emmy Award for Outstanding Art Direction for a Variety or Music Program the following year.

American neo soul singer Erykah Badu noted that her 1997 debut album, Baduizm, was partly influenced by Norwood's debut album, while Barbadian singer Rihanna said of her 2007 album Good Girl Gone Bad, "[Brandy] really helped inspire that album. I listened to [Afrodisiac] every day [while in the studio]." Kelly Rowland cited Norwood, who also wrote and produced for Rowland's debut album, as one of the inspirations for her second studio album Ms. Kelly (2007). Rock musician John Frusciante, former guitarist of rock group Red Hot Chili Peppers cited Norwood as the "main inspiration" behind the guitar work on Red Hot Chili Peppers' 2006 album, Stadium Arcadium. When discussing the work on her debut project H.E.R., singer H.E.R., who worked with the producer DJ Camper, revealed that Brandy was a "huge inspiration" to her, and that her being inspired Brandy impacted her musical output.

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. Originally bought by CBS, the program debuted on UPN in January 1996, and soon became their most-watched show. While the sitcom managed to increase its audience every new season and spawned a spin-off titled The Parkers, the network decided to cancel the show after six seasons on the air, leaving it ending with a cliffhanger for a scrapped seventh season. Norwood was awarded an NAACP Image Award for Outstanding Youth Actor/Actress for her performance. In 1997, Brandy, Ray J, and their parents started The Norwood Kids Foundation, which helps disadvantaged, at-risk youths in Los Angeles and Mississippi through the arts and self-help programs.

After backing out of a role in F. Gary Gray's 1996 film Set It Off, Norwood made her big screen debut in the supporting role of Karla Wilson in the slasher film, 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 to 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 a Blockbuster Entertainment Award and an MTV Movie Award nomination for Best Breakthrough Female Performance. In 1999, she co-starred with Diana Ross in the telefilm drama Double Platinum about an intense, strained relationship between a mother and daughter. Shot in only twenty days in New York City, both Norwood and Ross served as executive producers of the movie which features original songs from their respective albums Never Say Never (1998) and Every Day Is a New Day (1999), as well as previously unreleased duets. The same year, Norwood headlined VH-1's Divas Live '99, alongside Whitney Houston, Tina Turner, and Cher.

Norwood attended Hollywood High School, but studied with a private tutor beginning in 10th grade. In 1996, she had a brief relationship with future Los Angeles Lakers player Kobe Bryant, whom she accompanied to his prom at Lower Merion High School in Ardmore, Pennsylvania. She also dated Boyz II Men lead singer Wanya Morris, whom she cited as her "first love." Morris, who is six years older than she, reportedly ended their relationship a month before her nineteenth birthday. Also during their work on the Never Say Never album, she briefly dated rapper Mase.

In 1996, Norwood along with her brother Ray J, created the Norwood Kids Foundation. Its goal of is to "use performing arts as a catalyst to shape the youth of today into self-confident, disciplined, responsible, and caring individuals capable of making a positive impact in their communities." In 1999 Brandy was the first international spokesman person for youth by UNICEF. Norwood is also an avid supporter of the Make A Wish Foundation and RAINN. In 2000, Brandy donated $100,000 to 2000 WATTS, an entertainment community center founded by singer Tyrese Gibson in the underprivileged community of Watts, California. Brandy teamed up with Skecher's “Nothing Compares to Family” campaign in 2008. In 2010 Norwood became involved with Get Schooled, a national non-profit mobile phone calls by celebrities to wake up students for school. In 2014, Norwood teamed up with "text4baby", which spreads health and wellness to expecting moms via text message, and became an honorary co-chairman of the 2014 Unstoppable Foundation. In 2018, she also appeared in a PSA for the American Heart Association and Hands-Only CPR with fellow Chicago the Musical cast members.

Brandy went on to sell over six million copies worldwide, and produced three top ten hits on the Billboard Hot 100, including "I Wanna Be Down" and "Baby", both of which reached the top of the Hot R&B Singles chart and were certified gold and platinum by the Recording Industry Association of America. "Brokenhearted", a duet with Wanya Morris of Boyz II Men, became a number-two hit on the charts. 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 1995, she finished a two-month stint as the opening act on Boyz II Men's national tour, and contributed songs to the soundtracks of the films Batman Forever and Waiting to Exhale, with the single "Sittin' Up in My Room" becoming another top-two success. In 1996, Norwood also collaborated with Tamia, Chaka Khan, and Gladys Knight on the single "Missing You", released from the soundtrack of the F. Gary Gray film Set It Off. The single won her a third Grammy nomination in the Best Pop Collaboration with Vocals category.

Since her 1994 debut album, Brandy has sold more than 40 million albums worldwide with over 8.62 million albums sold in the United States alone. According to the RIAA Brandy has 10.5 million Gold & Platinum certification's. Her song "The Boy Is Mine" is also one of the longest running number one songs in the United States, and is one of the best selling duets of all time. In 1999, Billboard ranked Norwood among the top 20 of the Top Pop Artists of the 1990s. In 2010, Billboard included Norwood in their Top 50 R&B and Hip Hop Artists list of the past 25 years. Norwood was one of the youngest artists nominated for the Grammy Award for Best New Artist. Her second album Never Say Never appeared in the "Top 100 Certified Albums" list by the RIAA.

In 1993, Williams hired producer Keith Crouch and R&B group Somethin' for the People to work with Norwood, and within eight months the team crafted Brandy. A collection of street-oriented rhythm-and-blues with a hip hop edge, whose lyrical content embraced her youthful and innocent image in public, Norwood later summed up the songs on the album as young and vulnerable, stating, "I didn’t really know a lot—all I wanted to do was basically sing. You can just tell that it’s a person singing from a genuine place, and also a place of basically no experience. I was singing about being attracted to the opposite sex, but I had no experience behind it." Released in September 1994, the album peaked at number twenty on the U.S. Billboard 200. Critical reaction to Brandy was generally positive, with AllMusic writer Eddie Huffman declaring Brandy "a lower-key Janet Jackson or a more stripped-down Mary J. Blige [...] with good songs and crisp production." Anderson Jones of Entertainment Weekly asserted, "Teen actress Norwood acts her age. A premature effort at best, that seems based on the philosophy 'If Aaliyah can do it, why can't I?'."

In 1990, her talent led to a contract with Teaspoon Productions, headed by Chris Stokes and Earl Harris, who gave her work as a backing vocalist for their R&B boy band Immature, and arranged the production of a demo tape. In 1993, amid ongoing negotiations with East West Records, Norwood's parents organized a recording contract with the Atlantic Recording Corporation after auditioning for the company's director of A&R Darryl Williams. To manage her daughter, Norwood's mother soon resigned from her job, while Norwood herself dropped out of Hollywood High School later, and was tutored privately from tenth grade on. During the early production stages of her debut album, Norwood was selected for a role in the short-lived ABC sitcom Thea, portraying the daughter of a single mother played by comedian Thea Vidale. Initially broadcast to high ratings, the series' viewership dwindled and ended up running for only one season, but earned her a Young Artists Award nomination for Outstanding Youth Ensemble alongside her co-stars. Norwood recalled that she appreciated the cancellation of the show as she was unenthusiastic about acting at the time, and the taping caused scheduling conflicts with the recording of her album. She stated, "I felt bad for everybody else but me. It was a good thing, because I could do what I had to do, because I wanted to sing."

Norwood's initial sound was contemporary R&B, heavily rooted in gospel and hip hop soul. Her lyrics spoke of various types of love, from casual and friendly love to romantic and spiritual affairs. Influenced by Houston and Carey, she incorporated adult contemporary pop and an emphasis on smooth, mature R&B ballads into the sound for her second studio album Never Say Never. Her third studio album Full Moon saw Norwood, and her then-creative partner Rodney Jerkins, experiment with blending her previous R&B sounds with futuristic, forward-thinking productions, including influences of electro-funk. Along with her style, her voice had gone through an evolution, with her light, girlish voice becoming much deeper, warmer, and smokier than it had been throughout the 1990s. The lyrics also reflected the change, as the album explored more adult, sexual topics and focused on both physical and emotional aspects of an intimate relationship. In 2004, her recent motherhood, life experiences, and growing affinity for British rock band Coldplay, caused her to shift toward a more experimental vision her fourth studio album Afrodisiac. The album, a collaboration with producers Timbaland and Kanye West, utilized the distinctive illbient aesthetic, which fuses ambient pop, dub, and breakbeat soundscapes with progressive sampling methods. A four-year hiatus and a few life-changing occurrences caused Norwood to return to the music industry in late 2008 with Human, her fifth studio album, which discussed topics of love, heartache and honesty. Experiencing a career and personal rejuvenation in 2012, Norwood was eager to scale back her previous album's pop style and return to R&B on her sixth studio album Two Eleven. The album was a melding of both Norwood's 1990s R&B sound and the bass-heavy trends of post-2000s contemporary hip-hop.

Brandy Rayana Norwood (born February 11, 1979), better known by her mononym Brandy, is an American singer, songwriter, record producer, and actress. Born into a musical family in McComb, Mississippi and raised in Carson, California, she began her career as a child and performed as a backing vocalist for teen groups. In 1993, Norwood signed with Atlantic Records. The following year, she released her self-titled debut album, which was certified quadruple Platinum in the U.S., selling six million copies worldwide. Norwood starred in the UPN sitcom Moesha as the title character, which lasted six seasons and resulted in numerous other roles. She resumed her music career in 1998 with the wildly 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. This launched her into international stardom, with films, endorsements, sold out concert tours, and her own line of Barbie dolls.

Norwood was born on February 11, 1979, in McComb, Mississippi, the daughter of Willie Norwood, a gospel singer and choir director, and his wife, Sonja Norwood (née Bates), a district manager for H&R Block. Brandy is the older sister of entertainer Ray J, as well as a cousin of rapper Snoop Dogg and WWE wrestler Sasha Banks. Raised in a Christian home, Norwood started singing through her father's work as part of the local church choir, performing her first gospel solo at the age of two. In 1983, her parents relocated to Los Angeles, California, where Norwood was schooled at the Hollywood High Performing Arts Center. Norwood's interest in music and performing increased after becoming a fan of singer Whitney Houston at the age of seven, but at school, she experienced trouble with persuading teachers to send her on auditions as she found no support among the staff. Norwood began entering talent shows by the time she was eleven, and, as part of a youth singing group, performed at several public functions.