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At age sixteen Tiger JK met Micki Eyes, later to be a member of Drunken Tiger, and performed in a rap festival in Los Angeles. He later caught the eye of Oasis Entertainment of South Korea, got signed, and released his first solo album, Enter The Tiger. The album achieved major success, but due to censorship, the songs were banned from being played from radio stations. Soon after the album and American rapper Ice Cube's highly controversial song Black Korea , Tiger JK teamed up with east coast rapper DJ Shine, and together the duo formed Drunken Tiger in 1998. Although the group was formed in the U.S., the group debuted in South Korea as well. The group immediately gained major popularity with songs such as I Want You and Do You Know Hip hop?.
Initially, Drunken Tiger was criticized for generating controversy due to their explicit content, and rebellious attitude towards mainstream music trends. Nevertheless, they continued to write their own music, perform in local shows, and gather a large following. The group would go on to release five albums, before DJ Shine would leave for personal reasons.
Throughout his career Tiger JK has also written and composed many Hip hop songs in South Korea for many well known Hip hop artists in the country. In mid 2006, Drunken Tiger established a Hip hop Record label named, Jungle Entertainment whose roster includes many well known Hip hop artists. Today, Tiger JK continues to perform under the Drunken Tiger stage name, and is still considered one of South Korea's most respected Hip hop artists