Maxwell scored his first Billboard Top 40 hit with 1996's "Ascension (Don't Ever Wonder)." Written and produced by Maxwell, the smooth single also won a Soul Train Music Award for Best R&B/Soul Single, Male. Check out vintage Maxwell above at only 23 years old. 

The moving single about a man’s love for a woman was composed and produced by R. Kelly for the soundtrack of the movie Life, starring Eddie Murphy. "Fortunate" won a 1999 Billboard Music Award for R&B Single of the Year and a Soul Train Music Award for Best R&B/Soul Single, Male. It was also nominated for a Grammy for Best Male R&B Vocal Performance. It was Maxwell's first number one single on the Billboard R&B chart. It was also number one on the Urban Adult Contemporary charts.
 

This single is romantic gold. "Sumthin' Sumthin': Mellosmoothe" appeared on the track of the 1997 film Love Jones, starring Larenz Tate and Nia Long, which is regarded as a Black cult classic and one of the best romance movies of all time. Originally it was the third single from Maxwell's 1996 debut album, Urban Hang Suite, "Sumthin' Sumthin,'" peaking at No. 10 on the Urban Contemporary chart. However, the version from the Love Jones is a fan favorite, listen above.

From Maxwell's 2001 Now album, "Lifetime" was nominated for a Grammy Award for Best Male R&B Vocal Performance. It reached number five on the Billboard R&B chart, and Now became his first No. 1 album. See the music video for the song above.
 

Maxwell’s super sexy single, "This Woman's Work," appeared as a studio version on his  Now album in 2001. However, it was also released in 1997 for an MTV Unplugged live album. The song was originally released by Kate Bush in 1989. Maxwell managed to take a powerful song from a woman's perspective and turn it into a heartbreaking ballad about longing for love.

After a sever-year hiatus from the release of his last recording, Maxwell returned in 2009 with BLACKsummers'Night, and a Grammy winning smash single,“Pretty Wings.” The single peaked at No. 1 in 2009 on the Billboard R&B chart. In an interview with MTV News, he described the song as “a bittersweet love song about meeting the right girl at the wrong time." 

After seven nominations, he won his first Grammy in 2009 for Best Male R&B Vocal Performance for "Pretty Wings'' and Best R&B Album for BLACKsummers'Night. He made his Grammy stage debut at the 52nd GRAMMY Awards in 2010, performing "Pretty Wings" and "Where Is The Love'' with Roberta Flack.

Check out the official video of "Pretty Wings" below:

The song is the first track on his 2009 BLACKsummers'Night. He broke down the lyrics in an interview with NPR’s Michel Martin, but refused to reveal the name of the person for whom he wrote the song. He explained that "Bad Habits" is about “an addictive sort of fatal attraction.” Here is a snippet of the lyrics: “This is the highest cost. Take you and make you off. Live you and leave you lost. Will you forgive me? Asked out all over town. Drags you and keeps you down. Two times and I take a round. Will you forgive me?”” Whew, check out the song above.
 

It’s easy to mistake this song from Maxwell’s 2009 #1 album, BLACKsummers'Night, for one of his love songs. But he told VH1 the single, which peaked at No. 11 in 2010 on the Billboard R&B chart, was actually inspired by the wars in Iraq and Afghanistan. “The fact that we're fighting a religious war is crazy to me," Maxwell tells the entertainment outlet. “I mean, everyone should believe whatever they want to believe in, just don't mess with me. If your god is named this and my god is named that, it's cool.”  

“Love you” is another beautiful love song from the singer’s 2009 BLACKsummers' Night album. It was not released as a single, but it was nominated for a Grammy Award for Best Male Pop Vocal Performance. Maxwell sums up his soul music experience perfectly in a quote on the Grammys website: "Soul music is soul music. It can be wrapped up in a neo soul package; it can be called hip-hop soul. But soul is soul, and it's been around; it will never go away."

Maxwell and Alicia Keys reached No. 1 on the Billboard Urban Contemporary chart with "Fire We Make" from her 2013 album, Girl On Fire. Co-written by Maxwell, the song is a beautiful from duet from powerhouses of contemporary soul. 

In 2021, 25 years after his first single was released, "OFF" charted at No. 1 on Billboard's Urban adult contemporary chart. In the beautiful song, Maxwell sings, “I see you in the dark / And like a moon-lit spark / I’ve never been so in awe / Creamy chocolate work of art." It was a full circle moment, 25 years of endless hits with die-hard fans by his side.

Happy birthday, Maxwell!