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Tsai's music has been the subject of music analysis and scrutiny.

China Times commented that what has brought Tsai success is "certainly not outstanding natural talent.

In July 2008, she earned a Butterfly Award from the Ministry of Labor of Taiwan, and was acclaimed as a role model in the music industry.

In early 2009, Tsai and Ken Erman, the founder of the fashion brand Truth and Pride, co-founded a fashion brand, Seventy Two Changes, which was named after her 2003 studio album, Magic (also known as See My 72 Changes literally in Chinese), to include apparel and accessories; Tsai released her eleventh studio album, Myself, in August 2010.

Tsai commented that "I have been a huge fan of Madonna. I would like to be a star like her." During her J1 World Tour (2004–2006), Tsai appeared onstage on a rising platform and struck yoga poses, and later she claimed that it was inspired by Madonna's live performance during her Re-Invention World Tour (2004); Tsai commented, "pop singer should challenge pre-existing concepts and lead audience to accept new genres of music; Madonna's works were controversial and somewhat critically panned when just released, but after years they were considered masterpieces." In a public interview, Tsai spoke about comparisons to Hamasaki: "Fashion is a prevailing trend in the style in which a person dresses, but there is nothing to do with copy; I feel honored to be compared with her, but we are different though we have similar fashion sense." Since 2007, Tsai has been invited to watch the "Big Four" fashion weeks, Met Gala, and Victoria's Secret Fashion Show, made her the first Chinese singer that has been officially invited to attend all of these notable fashion events.

In 2006, FHM Taiwan ranked her first on the "100 Sexiest Women in the World" list.

With four songs–"Marry Me Today", "Sun Will Never Set", "Honey Trap", and "Play"–topping the chart, she became the singer with the most number-one songs on the chart, leading to a tie with Taiwanese singer Jay Chou.

In December 2004, Tsai released her second remix album, J9, which contains the Hit FM Top 100 number sixty-one hit, "Signature Gesture".

In March 2005, she signed with a contract with publisher Yuan Shen to be the author of a series of English reference books.

She cited Whitney Houston and Mariah Carey her "two favorite artists" whom she would often sing along to in her childhood.

Since Dancing Diva (2006), Tsai has drawn comparisons to Madonna in terms of stage presence.

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In 2010, Forbes ranked Tsai seventh on their "Forbes China Celebrity 100" list with NT$222 million, made her the highest-paid Chinese female singer of the year.

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