YMCMB’s First Blue-Eyed Rapper – Caskey

When it comes down to it, the best white rappers to ever do it are Eminem, RA The Rugged Man and the Beastie Boys. Often times, when the white rapper conversation is brought up people discuss names such as Mac Miller, Asher Roth, Machine Gun Kelly, Lil Dicky, Macklemore and Yelawolf. These artists are all valid but one name worth mentioning within that same category caliber is Caskey.

Cooking with Caskey

Brandon Caskey hails from Orlando, Florida and is a rapper by conversion. Originally, this man strictly listened to the genre of heavy metal and did not even have any inkling of becoming a hip-hop artist. It wasn’t until his older sister put him on to hip-hop material such as NWA, Three Six Mafia and Nasir Jones that he began to grow an appreciation and fondness of the crafty genre. As a heavily reserved metalhead, Caskey did not foresee rap within his future, whatsoever. His entire approach changed when he heard the music and met some important individuals within the game.

Throughout high school, Caskey spent time fine-tuning his abilities and leveraging his popularity to build a consistent fanbase. After garnering significant traction from peers within the student body, Caskey began to take his hip-hop career more seriously. The support from his friends and those close to him gave him proper recognition and opened his eyes to the potential breadwinning abilities he could create from music.

Emotion and Energy

Some of the artists that Caskey began to come in contact with were the deciding factor in his decision to become a mainstay within the hip-hop atmosphere. As a metal connoisseur, the producers and top executives that he encountered truly shifted his perspective and made him choose to invest his talent within the realm of hip-hop music. One day, Caskey stumbled upon a DJ Khaled video and the distinct sound that he heard is what flipped his outlook on hip-hop. Learning from important individuals and seeing the types of success that is possible from remaining persistent were key components to developing his artistic persona. Together with collaborators and friends, Caskey formed the collective by the name of, “Keep Pushin Entertainment” which has been going for a decade strong.

As a level-headed contributor to the game, Caskey is a high energy individual. With heavy emotional context and a diverse background, this man has made many strides from the inception of his career. For him, music is a medium by which he lives his life through. Caskey delivers fulfillment, enjoyment and purpose within his musical database and it resonates with the listeners. One thing that is very special about Caskey is the way that he allows his sound to reside neatly with the beat. Often times, the vibrations and wavelengths of the beat will lead him to alter his delivery, inflection, enthusiasm and emphasis to create a timeless track. He is able to develop music that submerges his persona seamlessly in with those around him which complements each person involved.

Reputation and Renown Recognition

A major turning point in Caskey’s career arrived after the release of his, “No Complaints” mixtape which was produced by The Avengerz. Alongside DJ Nasty, Caskey was able to diversify his outreach by becoming familiar with the likes of YMCMB. Upon catching wind of Caskey’s ability and spark, DJ Nasty passed along some of Caskey’s music to Birdman and Ronald Williams, the brother duo at the head of Young Money Cash Money Billionaires. As Caskey continued to pump out musical content and prove his hit-making ability, YMCMB continued to stay in tune with his output.

In August of 2012, Caskey and YMCMB came to an agreement in accordance with Republic Records to roster this Florida native. As the first “blue eyed rapper” on the team, Caskey brought an edge and flair to the squad that allowed them to diversify their approach. As a lyrically intrinsic and inventive artist, his songwriting and consistent outpouring of musical records proved to be a selling point for YMCMB. His first Cash Money album release, Black Sheep 2 arrived in 2015 and was well received within hip-hop circles. Caskey also made his way onto the star-studded Rich Gang compilation album which featured the likes of Rich Homie Quan, Young Thug, Future, Nicki Minaj, T.I. Lil Wayne, French Montana, Kendrick Lamar, Rick Ross and others.

Superlative Stand Out

As a verified vocalist and in-depth writer, Caskey brings an element of difference making to the genre. His song, “100 Bars” showcases his pristine ability to flow on a track for an extended period of time. There are many things that Caskey does that are rather unheard of within the modern era of rap. As a multifaceted artist, he has outstanding depth and breadth of lyrical content that speaks volumes and is reflected mightily within his catalogue. By blending a mixture of musical backgrounds into various soundscapes, Caskey is able to reach a wide audience of people who love quality music. His raw expressions of emotion are a direct acknowledgement of the heavy metal genre and the music that he was became enamored with as a youngster. He is unafraid to showing the fans his vulnerabilities, imperfections and personal life as he constantly presents the most authentic version of himself to his fanbase. As heavy metal drew him to becoming interested in music as a listening consumer, hip-hop drew him to becoming a producer of music that is able to truly affect the sound and bridge the generational divide.

One thing that has hampered Caskey’s career is a common theme amongst YMCMB artists. YMCMB struggles to develop their artists by only managing to keep them afloat. To grow, an artist needs to consistently put out projects, learn from experimentation and thus improve according to what the market demands. Without a steady output of music, fans become disinterested. Also, failure to compensate the artist completely and punctually can lead to dissatisfaction between all parties. YMCMB is notorious for pushing back release dates and creating divides between their management and the artists. By staying out of touch with the artists’ necessities and remaining at a distance, it is difficult for any scenario to result in positive gain. For instance, the last album to be released from Caskey alongside his label came out in 2016. To this day, he is still aligned with CMB and Mack Money for publishing, marketing and merchandising.


Here are a few interesting facts about Caskey:

He lost his virginity at age fifteen inside of Pleasure Island at Disneyland while watching a heavy metal favorite, Norma Jean perform during a House of Blues Show. He was involved in a motorcycle accident that pinched the nerves in his arm and caused him to release his mixtape, “Homegrown” a little later than expected. His father committed suicide when he was only sixteen years old and he delves into the topic in detail on the song, “Letter to my Father.” He embarked upon the White Clouds tour in 2014 with Lil Debbie and expanded his worldviews and perspectives during that time period. He frequently collaborates and creates records in the Hit Factory near Miami, FL. Caskey continues to release music under the “Black Sheep Records” label and keeps him YouTube page stocked with new singles and video documentation of his journey.

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