Caskey

Brandon Robert Caskey (born August 28, 1992), known mononymously as Caskey, is an American rapper and entrepreneur hailing from the Orlando area of Florida, specifically Winter Springs. He is an artist renowned for his complex lyrical style, which often incorporates dark, spacey, and emotional elements, distinguishing him within the contemporary hip-hop landscape.

Roots in Florida Hip-Hop: KPE

Before his rise to national prominence, Caskey was a significant figure in the Central Florida hip-hop scene. He was an early and foundational member of the rap collective and record label, KPE (Keep Pushin Entertainment), a group known for its diverse lineup of Florida talent. His time with KPE laid the groundwork for his collaborative skills and allowed him to hone the unique blend of technical rapping and emotional depth that would define his sound.

Early Career and Major Label Signing

Caskey’s early musical influences were broad, ranging from heavy metal in his youth to foundational rap groups like N.W.A and Three 6 Mafia, and lyrically complex artists such as Nas and Eminem. He began writing raps during his sophomore year of high school and cultivated a dedicated following through independently released mixtapes, including Blowin’ Out My Mind Vol. 1 and The Intangibles.

His career saw a massive acceleration in August 2012 when he caught the attention of Birdman, the co-founder of Cash Money Records. Impressed by Caskey’s online videos, the mogul signed him to Cash Money Records, an imprint of Republic Records. This major-label signing instantly boosted his profile. His debut mixtape re-release, No Complaints, and a feature on the 2013 Rich Gang compilation album cemented his entrance into the mainstream, establishing him as a young artist with undeniable commercial potential.

Creative Work and Independent Success

During his tenure with the label, Caskey released several well-received mixtapes on Cash Money/Money Mack Music, including The Transient Classics (2013) and the popular Black Sheep series. His music, characterized by sharp introspection and moody production, resonated deeply with listeners.

After an amicable departure from Cash Money in 2020, Caskey embraced full independence, operating through his own Black Sheep Records imprint. This move ushered in an extremely prolific period, where he has maintained his relevance and chart success without the backing of a major label. A key moment in his independent run was the 2021 collaborative album Yelawolf Blacksheep, which achieved commercial success and reached the Billboard Top Album Chart. His subsequent independent albums, such as While You Wait for J.A.W.S. and This Isn’t Even My Final Form (both 2022), have consistently showcased his strong following, reaching the #1 spot on the iTunes Hip-Hop Album Chart. In 2023, he continued his output with the release of the album Cadillac Music.

Caskey’s “Black Sheep” sound—a fusion of melodic trap, deeply personal lyricism, and raw emotional delivery—is his signature. Beyond his music, he continues to engage directly with his fanbase, notably through his popular and unconventional online series, “Baking with Caskey.”