In 2007, Michael signed a contract with Columbia Records and released a single "Kickin" for his upcoming album Fearin' and Loathin' in Smalltown, U.S.A.
However, the LP never came out, and the label canceled the contract. Two years later, the singer signed another contract with a new label, Ghet-O-Vision Entertainment and recorded an EP, Arena Rap.
In 2010, Yelawolf worked with Bizarre from D-12 to record the LP, Friday Night At St.Andrews. The same year he helped such artists as Big Boi, Paul Wall, and Juelz Santana record songs for their albums. In November, with the assistance of the labels, Ghet-O-Vision Entertainment and Interscope Records, the singer presented a mixtape, Trunk Muzik 0-60.
In 2011, the rapper appeared on the cover of a popular music magazine, XXL together with Eminem and other members of Shady Records 2.0, Slaughterhouse. The same year, Michael recorded his debut official LP, Radioactive.
In 2012, Yelawolf worked with Ed Sheeran to record a promotional single, "You Don't Know (For Fuck's Sake)". The same year, Michael presented his new song “Happy Father's Day", produced by Alabama from M16. At that time, many fans wanted to book Yelawolf for private events, but he was mostly busy with studio work.
In February 2013, the rapper recorded the leading track “Way out” for his upcoming mixtape, Trunk Muzik Returns and announced the release date. After some time, he presented a new song, “FAST Ride" and then another one, "Gangster". The mixtape featured 10 original tracks. All of them were produced by WLPWR.
In October 2013, the rapper released another mixtape, Black Fall, which included five tracks. All of them were produced by DJ Paul from Three 6 Mafia. At the beginning of 2014, Michael presented the first single, "Box Chevy V", from his upcoming LP, Love Story. The album was supposed to come out in May, but the release was delayed until the spring of the next year. Eminem was the only invited artist, who worked on the album. The LP featured Yelawolf’s most successful single, "Till It's Gone".
The album, Love Story, is the rapper’s most successful LP to date. However, at first, critics gave it many negative reviews due to the uncommon combination of hip-hop and country. Two music videos for singles "Best Friend" and "Till It's Gone", recorded with Eminem collected over 100 million views.
In September 2015, Yelawolf released his next album, Trial by Fire. The rapper produced it together with the members of his touring group, DJ Klever and Bones Owens.
In 2016, Yelawolf took a break due to health problems. When he came back, the singer decided to change his style. After a year, Michael recorded a single , "Row Your Boat", from an unfinished album, Trial by Fire. The LP finally came out in October 2017.
In 2019, the artist released a new album, Trunk Muzik III, with the assistance of Shady Records. After the release, Yelawolf embarked on a tour to support the LP. After some time, he announced working on a new album, Ghetto Cowboy, the release date of which is currently unknown.
