2010–2012: Beginnings and signing with Cash Money

Throughout his childhood, Caskey would write other genres of music, and eventually began writing raps in his sophomore year at Winter Springs High School.^[4][3] Then in his early years, he released two underground mixtapes, Blowin' Out My Mind Vol. 1 and The Intangibles.^[5] While recording his third official mixtape Homegrown Vol. 1 he linked up with Orlando, Florida-based production team The Avengerz.^[3] A few weeks prior to its release he was in a motorcycle accident, where he suffered pinched nerves in his left arm.^[6] On April 20, 2011, Caskey released Homegrown Vol. 1 as a free download.^[7]

In August 2012, Caskey released his fourth official mixtape titled No Complaints, which was produced by The Avengerz.^[8][9] The mixtape would be heard by Cash Money Records producer DJ Nasty, who would pass it on to CEO Birdman. Upon hearing it and meeting with Caskey, Birdman said he immediately knew he was a star.^[10] In early August 2012, Cash Money Records released a video of Caskey officially signing to the label. The video also revealed that his debut studio album would be released in the following year.^[11][12] Upon signing he said: "I’ve wanted to be a performer my whole life, so signing with Cash Money Records and having this platform to release my music has been a dream. I greatly respect Birdman, Slim and the YMCMB family. I look forward to making the city of Orlando, my fans and my label proud."^[13] To celebrate he released "Cash Money Records 100 Bars" on September 13.^[14]

2012–present: The Transient Classics, Black Sheep 2, Yelawolf Blacksheep and This Isn't Even My Final Form

On December 8, 2012, he released his debut single "Keep It on the Low" featuring Kyle Denmead from the No Complaints mixtape.^[15] He had a solo track titled "FBGM" on the YMCMB mixtape Rich Gang: All Stars, which was released on February 18, 2013.^[6] Then on February 25, 2013, Cash Money re-released No Complaints with two bonus tracks.^[16][17] He was featured on the Cash Money Records compilation album Rich Gang, on the song "Sunshine" also featuring Birdman, Limp Bizkit and Flo Rida.^[18] Artistdirect would call the song one of the album's standout tracks.^[19]

On June 24, 2013, Caskey announced that his upcoming mixtape would be titled The Transient Classics.^[6] On July 16, he revealed the cover art for The Transient Classics and announced it would be released on his 21 birthday, August 28, 2013.^[6] On August 20, 2013, he released the music video for the song "Show Me Some", which was shot in Paris, France.^[20][21] The mixtape was produced by The Avengerz, Myles William and The Colleagues and featured guest appearances from Trae tha Truth, Machine Gun Kelly, Riff Raff, JellyRoll, Rittz, and others.^[22] Upon its release it was met with positive reviews from music critics.^[23] His debut album was recorded at The Hit Factory in Miami, its release was and debuted on 2014. On April 14, 2015, Caskey released a mixtape titled "The Lost Files."^[24] On September 7, 2015 Caskey released an album titled Black Sheep 2 with production primarily by Anonymass. It would go on to become one of his most acclaimed projects. He would then follow up with Black Sheep 3, Generation, Speak of the Devil, Music to Die To, Black Sheep 4, Clockwork, Viral, the latter featuring one of his most streamed songs "Martial Law". He secured his first number one on the iTunes Hip Hop charts with his album This Isn't Even My Final Form (2019). His third album was released in December 2022 titled While You Wait for J.A.W.S., which secured another number one on the iTunes Hip Hop chart. Caskey has since released the singles "I'm a Virgin" and "Firestarter", also produced by Anonymass.

Studio albums

Collaborative albums

Compilation albums

Mixtapes