After starting out performing in a Hip Hop style, a series of mixtapes and independent releases, particularly Stereo: A Hip Hop Tribute to Classic Rock and Arena Rap, introduced a Rap Rock style. His 2010 mixtape Trunk Muzik marked his breakthrough, and helped him develop a substantial online following. In 2010 and 2011, he raised his profile further via appearances on albums by rappers Big Boi, Paul Wall, TechN9ne, Gucci Mane, and Big K.R.I.T., leading to him signing with Eminem's Shady Records label, the same year he was featured in XXL's Top 11 Freshmen of 2011. After working more in a Hip Hop style for his Shady Records debut, Radioactive, the mixtape Trunk Muzik Returns and subsequent albums Love Story and Trial by Fire saw a return to the Rap Rock style of Yelawolf's indie releases, as well as seeing him begin to incorporate elements of Country Music into his music.
Since leaving Shady Records in 2019, Yelawolf has predominantly released recordings through his own record label, Slumerican.
He is married to singer Fefe Dobson, who appeared on his Shady Records debut, Radioactive.
Yelawolf demonstrates examples of the following tropes:
- Concept Album: Stereo is a Concept Mixtape in which he hijacks a Classic Rock radio station. All of the songs on the mixtape are heavily sampled from Classic Rock songs (Brick in the Wall, Rich Like Me, Brown Sugar, which was named after the Rolling Stones song but actually samples a song by The Eagles, Heroine, TNT). Trial by Fire is also a Concept Album.
- Mighty Whitey: When Eminem told Kid Rock that he'd just signed the best unsigned rapper he'd ever heard (Yelawolf), Kid Rock presumed that Yelawolf would be black, due to white rappers outside of Eminem and Kid Rock having a reputation for not being good, but when Kid Rock went to shake the hand of a black member of Yelawolf's crew, he was informed that Yelawolf was white. Though Yelawolf is half-Cherokee, and the "Yela" part of his stage name is a Cherokee word meaning "sun".
- Mistaken for Racist: Due to the Confederate flag controversy (see Old Shame), Yelawolf was this; however, at that time, he was raising his three half-black children from a previous relationship, and his then-girlfriend, now wife, Fefe Dobson, is also black. Yelawolf subsequently cleared up the misconception on the non-album single "To Whom It May Concern", which made it clear that he is disgusted by racism and does not support any form of racism.
- Motor Mouth: One of the things that made Yelawolf stand out before his mainstream breakthrough was his fast rapping style.
- New Sound Album: Started out performing in more of a Hip-Hop style, before introducing a Rap Rock sound with his mixtape Stereo. Radioactive saw him returning to Hip Hop, while the mixtape Trunk Muzik Returns and the following albums Love Song and Trial by Fire saw him performing in more of a Rap Rock style and developing into a Country Rap style. Sometimes Y, his collaboration with Shooter Jennings, marked his first full Rock album with no rapping or Hip Hop elements.
- Old Shame: Yelawolf got in trouble in 2015 for defending the Confederate flag, but he very quickly reversed his position by releasing a non-album single called "To Whom It May Concern" which contextualized his earlier support of the Confederate flag as being connected to his Southern upbringing, and how he came to reject the Confederate flag out of his disgust towards the racism-motivated Charleston church shooting.
- Rap Opera: Trial by Fire is a bit of an autobiographical Rap Opera talking about his pre-fame life and personal and career struggles as he rose up from poverty to pursue his rap career.
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Retroactive Recognition: Yelawolf recorded collaborations with a large number of artists, Big Boi, Paul Wall, TechN9ne, Gucci Mane, and Big K.R.I.T. before he signed with Eminem's Shady Records.
