[7] Through the album and its follow ups, Maxwell has been credited—alongside Lauryn Hill, D'Angelo, and Erykah Badu—with popularizing neo soul for mainstream audiences in the late 1990s.

[8] His second and third albums, Embrya (1998) and Now (2001), both received platinum certifications by the Recording Industry Association of America (RIAA);[9] the latter became his first to debut atop the Billboard 200 chart.

His 1999 single, "Fortunate" was released for the R. Kelly-produced soundtrack to the film Life, and yielded his furthest commercial success as it peaked at number four on the Billboard Hot 100.

[16] According to him, the R&B of the early 1980s contained "the perfect combination of computerized instrumentation with a live feel", and that the genre's dynamics later became lost due to the influence of hip hop on R&B.

[17] Despite facing ridicule from classmates for being shy and awkward, he progressed and continued to develop his musical abilities, and he also adopted the look of a more bohemian style outwardly in his clothing, growing long sideburns and letting his hair grow out wildly and combed in an extreme style, or sometimes putting his hair in long thin braids.

[17] The demo engendered interest, and his official debut concert performance at Manhattan nightclub Nell's drew a crowd.

[17] During the next two years, Maxwell wrote and recorded over three hundred songs and played frequently at small venues throughout New York City.

[16] Maxwell's performances continued to draw interest and increase the buzz about him, and he was called "the next Prince" by a writer from Vibe magazine who attended one of his shows.

[19] However, it was shelved for nearly a year,[20] due to issues with Columbia's management, the label's extensive reorganization and record executives' doubts of the album's commercial potential.

[30] The album's fourth single, "Suitelady (The Proposal Jam)", entered the Hot R&B/Hip-Hop Airplay component chart in May 1997, peaking at number 64.

"[14] With its internal focus and esoteric grooves, the album served as a departure for Maxwell, who did not regret risking his reputation with urban listeners for a more challenging record.

[36] The album experienced a critical backlash similar to that of other artists' work that broke their previous releases' successful formulas in favor of more compelling projects, now being termed "neo-soul.

[38] In a retrospective review for Allmusic, Stephen Thomas Erlewine wrote that Maxwell "overstuffs his songs with ideas that lead nowhere" and called Embrya "a bit of a sophomore stumble, albeit one with promising moments."

[3] Despite the negative press, the album sold more than one million copies and garnered Maxwell a new alternative fanbase, but confounded the traditional urban consumers.

[40] Embrya was nominated for a Grammy Award for Best R&B Album, losing to fellow neo-soul artist Erykah Badu's Baduizm (1997).

[60][61] Maxwell received six nominations for the 2010 Grammy Awards, winning "Best R&B Album" for BLACKsummers'night and "Best Male R&B Vocal Performance" for "Pretty Wings.

[66] On December 18, 2014, Maxwell announced on the social media site Twitter the second installment of his trilogy blackSUMMERS'night would be arriving sometime in winter 2015.

[67] On April 7, 2016, Maxwell released his first solo single in 6 years titled "Lake by the Ocean", and also revealed his long-awaited fifth album blackSUMMERS'night.

[32] Maxwell had a consecutive four-night concert run at the Kennedy Center, supported by the National Symphony Orchestra, in September 2019.

Along with fellow musicians D'Angelo and Erykah Badu, Maxwell has been credited with helping to shape the "neo soul" movement that rose to prominence during the late 1990s.

[14][7] Along with D'Angelo's Brown Sugar (1995) and Badu's Baduizm (1997),[7] Maxwell's Urban Hang Suite has been recognized by writers for beginning neo soul's popularity and helping the genre obtain commercial visibility.

[75] Its columnist wrote that Maxwell's Urban Hang Suite "heralded the arrival of a top-of-the-class graduate of the old school of soul, one who could sing about romantic aspiration and tribulation with heart-wrenching emotion.

It was as if the aesthetic that Gaye ascribed to — 'music that has feeling, hope and meaning – all the things people are looking for' — had been rediscovered after a long, hedonistic interlude.

[16] On his emergence with Maxwell's Urban Hang Suite, writer Carol Brennan cited him, along with the Fugees, D'Angelo and Tony Rich, as neo soul musicians that "exhibited the identifying characteristics of this new breed of R&B artists: lyrics that give voice to intense personal expression, creative control over the music, and an unexpectedly successful debut.