Tsai exercises significant creative control over her career, and her work, which often addresses societal issues and ideological themes, has achieved both commercial success and critical acclaim.

Tsai has frequently appeared on the Forbes China Celebrity 100 list, ranking in the top 20 for six out of ten years since 2010 and being named the number one Chinese female singer three times.

[6] During her high school years, she formed a band named Twister with her classmates and participated in various singing competitions to enhance her university application profile.

[28] Despite being considered one of her most engaging works during her time with Universal, the album faced promotional challenges due to a contractual dispute with her management company, D Sound.

[35] On March 7, 2003, Tsai released her fifth studio album, Magic, co-produced by industry figures including Bing Wang, Peter Lee, Jamie Hsueh, Jay Chou, and Huang Yi.

[36] The album featured a diverse mix of genres, including pop, disco, funk, ballads, hip-hop, and Britpop, tailored to suit her vocal abilities and artistic vision.

[47][48] On February 27, 2004, Tsai released her sixth studio album, Castle, again collaborating with producers including Bing Wang, Peter Lee, Jay Chou, Jamie Hsueh, Huang Yi, and G-Power.

[61] This album, co-produced by Jamie Hsueh, Jack Chou, Bing Wang, and Adia, combined elements of pop, hip-hop, electronic, disco, and Chinese traditional music.

[71] Subsequently, on May 5, 2006, Sony Music released her greatest hits compilation, J-Top,[72] which sold over 100,000 copies in Taiwan and ranking as the fifth highest-selling album in the country for that year.

[75][76] Critics lauded the album for its rich content, sophisticated production quality,[77][78] and widespread appeal, solidifying Tsai's status as a prominent dance-pop artist in the Chinese music industry.

[85] The tour spanned two and a half years, encompassing 28 shows in 20 cities, attracting approximately 500,000 attendees and generating a box office revenue of around NT$1 billion.

[86] On September 29, 2006, she released the compilation album Dancing Forever,[87] which included the track "Marry Me Today", which won the Golden Melody Award for Song of the Year.

[101] Initially scheduled for release on March 7, 2008, the album's launch was delayed due to personnel changes and stock acquisition at EMI in Greater China.

[122] Co-produced by Andrew Chen, Adia, and Paula Ma,[123] the album centered around a party theme,[124] with dance music comprising ninety percent of its content.

[129] Tsai commenced her Myself World Tour on December 24, 2010, at Taipei Arena,[130] which lasted two years and four months, encompassing 35 shows in 31 cities and attracting approximately 600,000 attendees, generating about NT$1.5 billion in box office revenue.

[160] The tour lasted one year and two months, consisting of 34 shows in 23 cities and drawing an audience of approximately 600,000, with box office revenue of about NT$1.5 billion.

[164] Additionally, she released several theme songs for various projects, including "Give Love" for a Mother's Day campaign on May 12, 2017,[165] "We Are One" with Hardwell on June 20, 2017,[166] and "On Happiness Road" for the film of the same name on November 20, 2017.

[194] On October 31, 2023, she released the theme song "Someday, Somewhere" for the 2023 Taiwanese web series At the Moment,[195] receiving a joint nomination with Richard Craker for Best Composer at the Golden Melody Awards.

[199][200] Tsai remarked that she became a fan of Madonna after watching her perform,[201] and expressed a desire to "lead trends in music, stage, dance, and fashion" in the same vein of the singer.

[26][30] Tsai's 2003 album, Magic, combined elements of disco, funk, hip-hop, rock, and R&B,[37] and marked the singer's shift towards a predominantly dance-oriented musical direction.

[213][123] Muse (2012) is a pop record with styles encompassing mainstream and independent music, with tracks such as "Fantasy", "Dr. Jolin", and "Beast" drawing influences from trance, progressive house, and techno, respectively.

[221] Qu Er from Tencent Entertainment felt that Tsai's vocal skills have often been misinterpreted, and expressed that only a handful of singers can sustain such seamless breath control throughout an entire performance.

[243] Tsai was initially associated with a girl next door image upon her debut, which resonated with a younger demographic and led her to be dubbed a "Teenage Boy Killer" by the media.

Following a contractual dispute, she made a return with the album Magic (2003), showcasing a more fashionable and sexy image accompanied by energetic dance music.

[280] Liang Xiaohui of NetEase Entertainment suggested that when future generations reflect on the early 21st-century Chinese divas, Tsai might be the first name that comes to mind, in a similar vein to Madonna in the late 20th-century.

[274] Liao Yuanling of Business Today wrote that Tsai consistently uses her platform to advocate for gender equality, empowering minority groups to speak up for themselves.

[213] Hou Cheng-nan, an associate professor at the Department of Mass Communication at I-Shou University, remarked how Tsai "elevated" the landscape of Chinese dance music and "set a high standard that is difficult to surpass".

[153] Apple Music wrote that songs such as "Play" and "Ugly Beauty" not only served as "sharp societal critiques", but also helped set "new visual and creative standards for Mandopop".

"[229] Tsai has endorsed a wide array of internationally recognized brands and products throughout her career, including Absolut Vodka,[297] Adidas,[298] Always,[299] Balvenie,[300] Bausch & Lomb,[301] Bulgari,[302] Crest,[303] Diablo,[304] Dr. Jart+,[305] Dungeon & Fighter,[306] Gap,[307] Head & Shoulders,[308] Intel,[309] Knorr,[310] Levi's,[311] L'Oréal,[312] Lux,[313] MAC,[314] Max Factor,[315] McDonald's,[316] Mercedes Benz,[317] Morinaga,[318] Motorola,[319] Nars,[320] Olay,[321] Pepsi,[322] Pony,[323] Puma,[324] Quaker,[325] Rémy Martin,[326] Samsung,[327] Shiseido,[328] Standard Chartered,[329] Sunbites,[330] Swarovski,[331] Toyota,[332] Tropicana,[333] Uber Eats,[334] Valentino,[335] Vidal Sassoon,[336] Yamaha,[337] and 7-Eleven.

[345] The brand was initially sold at Nordstrom across 12 North American cities, with plans to expand into Asia, including Taiwan, China, Singapore, and Malaysia.