A Charlotte native, Hamilton began singing in his church's choir at age 17. He attended
South Mecklenburg High School, where he performed as part of in their award-winning choir directed by Mark Setzer. In 1992, he met producer
Mark Sparks, who encouraged Hamilton to leave Charlotte and head to
New York City, where he signed with
Andre Harrell's
Uptown Records. Hamilton co-wrote the 1999 hit "
U Know What's Up" for singer
Donell Jones. In 2000, he joined
soul singer
D'Angelo's international tour in promotion of the
Voodoo album, where he featured as a
backup singer.
Nappy Roots Hamilton was first introduced to mainstream audiences with after performing the chorus to
Nappy Roots 2002 single "
Po' Folks", which earned a
Grammy Award nomination for "
Best Rap/Sung Collaboration" in
2003. "
Po' Folks" is the second single from the debut album,
Watermelon, Chicken & Gritz (2002). Hamilton further collaborated with Nappy Roots on their songs the songs "Sick & Tired", "Push On", and "Organic" from their second studio album for
Atlantic Records:
Wooden Leather (2003); he also guest performed on the lead single—"Down N' Out"—to their third album,
The Humdinger (2008). Nappy Roots and Hamilton both guest performed on
Mark Ronson's 2003 song "Bluegrass Stain'd" from the latter's album
Here Comes the Fuzz.
2002–present Hamilton made a guest appearances on
Tupac Shakur's posthumous album
Better Dayz (2002)—on the album's second disc version of "
Thugz Mansion". In 2003 he released his debut album ''Comin' From Where I'm From'' that featured the hit single "Charlene". He guest featured on
Jadakiss' 2004 single "
Why", which peaked at number 11 on the
Billboard Hot 100 and received a
Grammy Award nomination for
Best Rap/Sung Collaboration. In the period 1999 to 2001, prior to his 2003 official debut, Hamilton's first compilation album,
Soulife was released in June 2005 and was composed of songs recorded . After the record company went bankrupt the recording were shelved. Arista asked Hamilton to revisited the material and with parts re-recorded, a selection was released as
Soulife in June 2005. ''Ain't Nobody Worryin'', his third studio album, was released on December 13, 2005 and received
gold certification by the
Recording Industry Association of America (RIAA). Hamilton guest appeared on a song from
the RH Factor's 2003 album
Hard Groove—"Kwah/Home". He appeared on
Angie Stone's "Stay For A While" in 2004. He made a guest appearance on
blues singer-guitarist
Buddy Guy's 2005 album ''
Bring 'Em In'', contributing vocals to a
cover version of
Bob Dylan's 1969 "
Lay Lady Lay", which featured
Robert Randolph. At the 2006
BET Awards, Hamilton won the
BET J "Cool Like That" Award. Comedian
Dave Chappelle had Hamilton as a musical guest on his show ''
Chappelle's Show'' in episode 6, Season 2 that premiered on
Comedy Central. In later 2006, he guest performed on Tupac Shakur's "
Dear Mama (Frank Nitty Remix)". He made a guest appearance on the
UPN show
All of Us in Season 2. Hamilton made a cameo as a soul singer in the film
American Gangster, to whose soundtrack he contributed. During the 2008 BET Awards, Hamilton performed
Al Green's "
Tired of Being Alone" during a tribute to Green's career. Later in 2008, he was featured on
Jeezy's album
The Recession, which peaked atop the
Billboard 200. In July 2011,
Jill Scott released her single "So In Love" featuring Hamilton. The song spent 19 weeks at number one on the Urban
adult contemporary charts. In 2012, Hamilton made guest appearances two successful releases for
Def Jam Recordings artists:
Big K.R.I.T.'s
Live from the Underground and
Life Is Good by
Nas, the latter of which debuted atop the
Billboard 200. Hamilton also co-performed on the
soundtrack to
Quentin Tarantino's
Django Unchained with his the song "Freedom", a duet with soul singer
Elayna Boynton. British DJ
Ben Pearce sampled vocals from Hamilton's song, "Cornbread, Fish & Collard Greens" in his 2013 song, "
What I Might Do". In February 2015, Hamilton made a cameo appearance on the television series
Empire, where he performed "Point of It All" as part of main character Luscious Lyon's proposal to his girlfriend. The episode aired February 4, 2015. In August 2015, Hamilton made a guest appearance on the song "That One", the first single from
Teedra Moses' second album
Cognac & Conversation. On February 24, 2016, Hamilton performed at the last "In Performance at the White House" hosted by President Barack Obama and First Lady Michelle as part of a tribute to singer
Ray Charles. On March 25, he released his sixth album ''
What I'm Feelin'' (2016), which he describes as an "emotional" cleanse reflecting on some of the hurdles he has faced. The album features guitarists
Gary Clark, Jr. and
Vince Gill, and songs produced by Mark Batson,
Salaam Remi, and
James Poyser, among others. Hamilton worked with the background singers the HamilTones, who often perform soul renditions of hip hop tracks. That same month, Hamilton partnered with
Cracker Barrel Old Country to release a deluxe version of the album sold online and in their stores. On March 28, 2016, Hamilton performed on NPR's critically acclaimed
Tiny Desk Concerts, where he performed his the singles "Amen", "Best of Me", "Cool", and "Charlene".
Chris Brown recruited Hamilton to perform on the "Legends" remix of his single "
Back to Sleep", which was released on April 10, 2016. On April 21, 2016, Hamilton embarked on a nationwide tour with
Fantasia. In 2017, Hamilton co-performed on the song "Carnival" for the virtual band
Gorillaz from their fifth album
Humanz. On May 15, 2020, Hamilton released the single "Back Together" featuring
Rick James through Hamilton's label My Music Box, in partnership with
BMG. The song was co-written by Hamilton and Ed D. Kane, and produced by
9th Wonder. It served as the lead single from his seventh album,
Love Is the New Black, released on September 24, 2021. On August 28, 2025, Hamilton and actor
Omari Hardwick released the collaborative album
Pages, a mixture of spoken word poetry and melody. ==Personal life==