Tsai Chen Nan is a Taiwanese singer, actor, composer, and lyricist born in Hsin-Kang, Chia-Yi, Taiwan. After completing elementary school, he began working various jobs in Taipei at age 13, including roles as a Taoist priest, Taiwanese opera actor, puppet master, magician, and clerk in different settings. By 16, he had not yet found a suitable job.

Tsai returned to Chia-Yi and briefly worked in a department store before his father introduced him to a motor factory in Fengyuan, where he apprenticed and saved money to buy a guitar. He taught himself to play and, at 18, joined a performance troupe, leaving his apprenticeship behind. He traveled extensively across Taiwan for a year and a half until the troupe disbanded.

Afterward, he worked temporarily at a hat factory run by his older brother, where he became engaged to a farmer's daughter. He moved to Nantun to continue working in the hat factory until he was conscripted for military service, but was discharged after 29 days due to being deemed unfit. Following his discharge, Tsai married and took over the hat factory from his father-in-law, eventually shifting the business to export leather bags.

Once the factory stabilized, he began writing songs, purchasing an electronic keyboard. At 26, he completed his debut Mandarin song, "You Don’t Love Me, I Love You," after several revisions. In 1979, he wrote more Mandarin songs and, through a friend, gained the attention of Sing-Cheng Record Company, although a government ban was placed on his songs due to its sarcastic lyrics.

In 1989, Tsai's factory closed amid an economic downturn. On December 15, 1994, he officially signed with Rolling Stone Records.

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