[1] He began his career in the late 1990s as part of the city's underground rap scene,[2] and signed with fellow Missouri-based rapper Tech N9ne's Strange Music as the label's first artist in 2004.

(2004),[4] and its follow-up, Feature Presentation (2008), were both met with critical praise; the latter debuted at number 60 on the Billboard Top R&B/Hip-Hop Albums chart.

[7] Calhoun's fourth studio album, Black Gold (2013),[8] debuted atop the Top Heatseekers chart and received continued critical praise.

[9][10][11][12][13][3] He parted ways with Strange Music in 2014 and subsequently founded the record label Black Gold Entertainment.

[16] By the 1990s he was involved in the underground hardcore rap scene of Kansas City, and he began actively recording in the late 1990s.

[2] Rapping professionally since 1998,[3] that year Calhoun appeared on the album Center Piece of the Puzzle by Snug Brim, using the alias Cutt Dawg.

[22] Rap Reviews greeted the album positively, writing "Calhoun has represented his hometown [Kansas City] admirably on B.L.E.V.E.

[26] A music video was shot for the album's single "Bunk Rock Bitch," and was released on January 15, 2009, with features from Tech N9ne and Krizz Kaliko.

[7] Meeting with a largely positive critical response,[11][12] the publication HipHopDX wrote that "Black Gold revels in its ability to highlight the unique approach of Strange Music while still sounding refreshingly conventional.

"[12] Like HipHopDX, David Jeffries of AllMusic also gave the album three and a half stars out of five, praising Calhoun's sense of humor in the lyrics.

[11] Calhoun decided to form his own imprint in 2014, and he split from Strange Music shortly afterwards[13] on amicable terms.

[15] Wrote MetroActive, on "the Kuttin Loose EP, he demonstrates a devastating flow, razor sharp wit and some downright nasty Dirty South production.

"[3] Among other themes, album's single "Handz Up (Shut Shit Down)" explicitly addressed police brutality, with Kutt directing the music video himself.