Never Say Never became Norwood's highest-selling and highest-charting album to date in most international markets, being certified quintuple platinum by the Recording Industry Association of America (RIAA) and selling over 16 million copies worldwide.

[16] Production for the album dates back as early as May 1997, during this time MTV News reported that Norwood was "taking up two recording studios in both New York and Los Angeles, and is working on what she hopes will be a fall release".

[23] Accompanied by his brother Fred Jerkins III and songwriter LaShawn Daniels, he ended up completing five songs in five days with her, including “Learn the Hard Way”, “Happy”, “Put That on Everything,” and title track “Never Say Never.”[23] Satisfied with their output, Atlantic Records secured a production deal with Jerkins's team and encouraged them to work on more material for the album.

[18] Jerkins and his circle worked excessively on the album, with typical sessions starting in the afternoon and lasting until the early morning hours.

[18] Despite the physical distance between the recording studios and Jerkins's native in New Jersey, he brought many of his family and friends to Los Angeles to help work on the album.

[23] With Jerkins being inspired by the singer/producer partnerships of Jimmy Jam & Terry Lewis and Janet Jackson as well as the influence of DeVante Swing on Jodeci's sound, he envisioned a full body of work for Norwood's second album, telling: "I wanted to make records where you fell in love with and heard the journey of the artists from beginning to end.

[29] Set as the album's lead single, "The Boy Is Mine" was originally intended to be a solo song for Brandy, but due to Monica's success at the time, it was conceived as a duet.

Inspired by Michael Jackson and Paul McCartney's 1982 duet "The Girl Is Mine", the lyrics of the mid-tempo R&B track revolve around two women fighting over a man.

The song's background revolves around Norwood telling a man "it's a shame you had to learn the hard way", and the lyrics quote: "You did me wrong / You told me lies / Treated me bad / All of the time."

The Guy Roche-produced "Almost Doesn't Count" follows; its lyrics revolve around its writer Shelly Peiken's powerful but unfruitful on-again, off-again relationship she had with a man while in college.

Entertainment Weekly describes her voice in the song as "soft and smoky" and as a "gospel-fired ballad that finds her effortlessly raising the roof".

[41] The co-marketing venture between Vibe and Atlantic Records resulted in a number of joint projects, such as a Vibe–Brandy website, a college marketing tour, and several retail and radio promotions.

[61] On January 11, 1999, Brandy and actress Melissa Joan Hart hosted the 1999 American Music Awards at the Shrine Auditorium in Los Angeles.

[65] On April 13, Brandy performed alongside Whitney Houston, Tina Turner, Cher, Chaka Khan, and Faith Hill, among others, at VH1 Divas Live '99.

[41] Atlantic also discussed plans with Disney for a cross-promotion between the home video version of Cinderella (1997) and the album, as well as the production of a major TV special, involving corporate sponsors.

In the United States, "The Boy Is Mine" became the best-selling song of the year, spending 13 weeks on top of the US Billboard Hot 100 during the summer of 1998.

The ballad reached the top twenty on the majority of all charts it appeared on and was promoted by a performance in the 1999 film Double Platinum, starring Diana Ross and Brandy herself.

Stephen Thomas Erlewine from AllMusic gave the album four out of five stars and noted it a "better, more adventurous record than her debut," adding: "Brandy wisely decides to find a middle ground between Mariah Carey and Mary J. Blige — it's adult contemporary with a slight streetwise edge.

However, given that a lot of R&B in the late 90s sounds like an ornate musical box revolving, the album is an intelligent brew that deviates sufficiently from that template and plays to Brandy and executive producer Rodney Jerkins's considerable strengths.

Verna felt that Brandy showed maturity and confidence on songs like "The Boy Is Mine"; yet the album as a whole was filled with “trend-conscious moves” from guest raps from Mase to “sound alike melodies ” similar to Janet Jackson.

[8] Although he indicated that it was "hard to argue with Brandy's deference to the rhythm, especially when she rides one of producer Rodney Jerkins itchily propulsive tracks," he also noted that it was flattening "its emotional range, until the romantic bliss of "Happy," the dogged determination of "Never Say Never," and the conflicted affection of "Angel in Disguise" all end up sounding pretty much the same.

[8] Angela Lewis, writer for The Independent was disappointed with the album, saying: "This is pop R&B without the soul, and could see Brandy without a future in the adult big league.

"[83] Music Week stated that due to her past success Brandy will have "little trouble storming the UK charts with this second album" and that she "displays a maturity beyond her years.

[104] In December 1999, the album was certified quintuple platinum by the Recording Industry Association of America (RIAA) for five million shipped units.

[116] Claire Lobenfeld from Fact found that while "Brandy's self-titled debut was sweet and flirty, its follow-up separated her from being just a pop singer with an accelerating star to one with something to say.

"[117] HipHopDX's Aaron McKrell remarked that "Brandy's newfound maturity was reflected in her music, and audiences and critics alike raved about the pop-tinged R&B that permeated the album,"[118] with Lela Olds, writing for The Boombox, further reporting that she "grew confident as both an artist and a young woman on Never Say Never, creating an album that showed both personal and vocal growth.

She felt that "it is arguably one of the best R&B albums of the 90s [...] There were a plethora of young female R&B singers at this time, but Brandy's star power allowed her to transcend genres by transforming her style of R&B into pop music.

"[121] In a similar article, Da’Shan Smith from Revolt noted that while the album "had an electric sensibility directed towards the approaching new millennium, they helped finalize the standard for what a pop&B diva's midtempos and ballads should consist of [...] Looking back at Never Say Never, one could argue that Brandy remodeled the construct of a teen-star-pushing-20.

"[120] Critics noted that her ability to grow musically while simultaneously balancing life as an actress served as role model material for other teen singers such as Britney Spears and Christina Aguilera who had upcoming studio debuts.

[124] The trio would go on to work with industry veterans such as Michael Jackson, Whitney Houston, and Toni Braxton as well as upcoming performers such as Jennifer Lopez and Destiny's Child, while reteaming with Norwood – to varying commercial and critical success – on her third and fifth studio albums Full Moon (2002) and Human (2008).