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.^[4] "Po' Folks" is the second single from the debut album, Watermelon, Chicken & Gritz (2002).^[5] 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).^[6][7] 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." 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. Hamilton's first compilation album, Soulife was released in June 2005 and was composed of songs recorded during the early part of his career. 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.^[8]

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.^[9] 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.^[10] 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.^[11] 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.^[12] The album features guitarists Gary Clark, Jr. and Vince Gill, and songs produced by Mark Batson, Salaam Remi, and James Poyser, among others.^[13][14] Hamilton worked with the background singers the HamilTones,^[15] who often perform soul renditions of hip hop tracks.^[16][17] That same month, Hamilton partnered with Cracker Barrel Old Country to release a deluxe version of the album sold online and in their stores.^[18] 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."^[19] Chris Brown recruited Hamilton to perform on the "Legends" remix of his single "Back to Sleep," which was released on April 10, 2016.^[20] 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.^[21]