Hamilton's second studio album, Comin' from Where I'm From (2003) received platinum certification by the Recording Industry Association of America (RIAA), earned four Grammy Award nominations, and spawned the 2004 single "Charlene", which peaked at number 19 on the Billboard Hot 100.

[3] His third and fourth albums, Ain't Nobody Worryin' (2005) and The Point of It All (2008), both peaked within the top 20 of the Billboard 200 and received gold certifications by the RIAA.

[4] Hamilton has won a Grammy Award from 12 nominations,[5] and is also known his song "Freedom" (with Elayna Boynton) which he co-wrote and performed for the soundtrack album to the 2012 film Django Unchained.

[8] 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.

[13] 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.

[21] He guest featured on Jadakiss' 2004 single "Why",[22] which peaked at number 11 on the Billboard Hot 100 and received a Grammy Award nomination for Best Rap/Sung Collaboration.

[23] 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 .

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).

[26] 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.

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.

[29] The album features guitarists Gary Clark, Jr. and Vince Gill, and songs produced by Mark Batson, Salaam Remi, and James Poyser, among others.

[33][34] That same month, Hamilton partnered with Cracker Barrel Old Country to release a deluxe version of the album sold online and in their stores.