He signed with Universal Motown Records to release his debut studio album, Country Boy (1999).

Richardson then co-wrote and performed on the track "Excuse Me", from Saadiq's 2002 Grammy Award nominated album Instant Vintage, as well as co-writing The Charlie Wilson single produced by Babyface "There Goes My Baby".

As of 2013, he has joined the upcoming reality series "Come Back Kings" with Ed Lover, Horace Brown, David "Davinch" Chance (of Ruff Endz), Jeff Sanders, Jameio, Mr. Cheeks and Black Rob.

[3][4][5] In January 2014, it was announced that Richardson signed a new deal with Eric Benét's label Jordan House Records[6] with distribution and marketing from the company Primary Wave Music.

[7] In April 2014, Richardson released the first single from his album "I Am Calvin" entitled "We Gon' Love Tonite".

Other artists that Richardson says has influenced him are Al Green, Marvin Gaye, Sam Cooke, Bobby Womack, K-Ci Hailey, and Stevie Wonder.