He is the grandson of businessman Hideki Yokoi, former president of the Hotel New Japan. The hotel’s flagship property in central Tokyo caught fire in 1982, disgracing Hideki Yokoi and causing Zeebra to be bullied by his classmates. Zeebra eventually dropped out of high school during his first year.

Zeebra began his hip hop career in 1993, joining the rap group King Giddra. Zeebra, along with his group King Giddra, played an important role in the development of the Japanese hip hop scene. In the mid 1990s, King Giddra, then an underground rap group, began addressing social issues of the time. King Giddra’s 1995 album “The Power from the Sky” discussed contemporary issues, particularly the economic recession and the inability of many Japanese college graduates to find employment. Zeebra addressed this issue of working towards a good education and being unable to find employment in his song “Bullet of Truth”. Through their music, Zeebra and King Giddra “challenged youth not only to recognize the difficulties faced by Japanese society but also to speak up about them.”

King Giddra’s popularity grew in Japan. In 1996, he recorded his first solo track “Untouchable” produced by Gang Starr producer DJ Premier. By 1997 Zeebra left King Gridda to start a solo career, appearing frequently in trendy hip hop and street culture magazines and TV shows about hip hop. In 1999 he released the single “Mr. Dynamite”, which became the first hip-hop single to make it into the top 50 on the Japanese Oricon pop charts. Through his early and newer work, Zeebra became one of the most popular and influential, yet controversial, Japanese hip hop artists.

In 2008, after the MTV Video Music Awards Japan Ceremony, an unhappy Zeebra went onto YouTube and published a video criticizing the MTV Japan for not appreciating musicians.

He married around the age of 20 and fathered two sons, Kento and Ren Yokoi, before divorcing his first wife. Ren is a DJ who plays a mixture of House and Techno, where he is also a main MC for Tokyo Scene; Tokyo’s radio show by Inter FM 89.7. He kept custody of both sons, and later remarried to Miwa Nakabayashi and fathered two daughters, Kanon and NiziU member Rima Yokoi. In November 2020, Zeebra and Nakabayashi announced that they had divorced.