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In December 2018, Tsai signed a recording deal again with Sony Music Taiwan. In the same month, she released her fourteenth studio album, Ugly Beauty. The album merged pop with an array of genres such as trap, house, reggae, and gothic rock, and it tended to break through the traditional aesthetic standard and explore the bipolarity of human feeling. Music critics responded positively towards the album, calling it the leading C-pop music production. The album topped the charts in China, Hong Kong, Macau, Malaysia, Philippines, Singapore, and Taiwan. The album became the best-selling album by a female artist of the year in Taiwan. The following year, the album became the best-selling digital album by a Hong Kong/Taiwanese female artist of all time in China, and made Tsai the best-selling digital Hong Kong/Taiwanese female artist of all time in the country. The lead single, "Ugly Beauty", topped the charts in China, Malaysia, and Taiwan and reached top ten in Hong Kong, Singapore, and Philippines. The song also reached number one on the Hit FM Top 100 Singles of the Year, made her the singer has the most number-one songs on the chart. In January 2019, Tsai served as a coach on the Chinese boy group survival reality television series, the second season of Idol Producer, with Lay Zhang, Li Ronghao, MC Jin, and Xu Minghao. In the same month, she featured on the promotional single titled "Happy New Year Do Re Mi" for the Chinese online video platform, Douyin. In May 2019, Ugly Beauty received seven nominations at the 30th Golden Melody Awards. The album was nominated for Album of the Year, Best Album in Mandarin, and Best Vocal Recording Album, the track "Womxnly" was nominated for Song of the Year, Tsai was nominated for Best Female Vocalist Mandarin, and Tsai together with Starr Chen were nominated for Best Single Producer for the track "Ugly Beauty". The album eventually won for Album of the Year, and the track "Womxnly" won for Song of the Year. In November 2019, Tsai collaborated with Chinese singer Karry Wang and released a single titled "Gravity". In December 2019, Tsai embarked on the Ugly Beauty World Tour. In April 2020, Tsai released a single titled "Fight as One" with Hong Kong singer Eason Chan to call for fighting against the COVID-19 pandemic.

Since the launch of her career, Tsai has endorsed a number of internationally famous brands, including Adidas, Always, Asus, Bausch & Lomb, BenQ, Bulgari, China Airlines, China Life, Crest, Gap, Dr. Jart, Dungeon & Fighter, Head & Shoulders, Hi-Chew, Intel, Knorr, Lay's, Levi's, L'Oréal, Lux, Max Factor, McDonald's, Mengniu, Mercedes-Benz, Motorola, Nars, Pechoin, Pepsi, Pony, Puma, Quaker, Rémy Martin, Samsung, Shisedo, Standard Chartered, Swarovski, Taiwan Beer, TalesWeaver, Toyota, Tropicana, Uber Eats, Xtep, Yamaha, and 7-Eleven. In December 2018, Pony announced that Tsai designed a limited edition of its classic M100 model which premiered on December 22, 2018. In July 2019, Gap announced that Tsai designed six limited edition t-shirts, which premiered on July 25 of the year and were inspired by the six tracks from her album Ugly Beauty (2018). On September 19, 2019, Gap launched four sweatshirts designed by Tsai.

In February 2016, Tsai joined the voice cast of Disney animated comedy-adventure film, Zootopia. She voiced a European rabbit named Judy Hopps who is a newly appointed member of the Zootopia Police Department in the film's Taiwanese version. In May 2016, Tsai performed at a special event held by South Korean music program broadcast M Countdown in China. In September 2016, Tsai collaborated with Swedish DJ Alesso and released an English single, "I Wanna Know", which reached number twenty-five on the Hit FM Top 100 Singles of the Year. At the same time, she and Alesso closed International Music Summit's Asia-Pacific event with a discussion of what it takes to bridge the gap between East and West in electronic music. In October 2016, she and Alesso performed the single, "I Wanna Know", and a remix version of her song, "Play", together at the Storm Music Festival in Shanghai. In the same month, Tsai collaborated with Taiwanese producer Starr Chen and released a new single, "Ego-Holic", which reached number fifty-two on the Hit FM Top 100. In December 2016, Tsai's songs has over 100 million downloads over the past ten years through Migu Music, an online music store under China's biggest mobile network operator China Mobile, made her the highest record sales for a female artist in Asia. In May 2017, Tsai released a new single, "Give Love", for the 2017 Mother's Day and a related public interest campaign presented by the Taiwan television station Da Ai Television. In June 2017, Tsai collaborated with Dutch DJ Hardwell and released an English single, "We Are One", which reached number ninety-nine on the Hit FM Top 100. In November 2017, Tsai recorded the theme song, "On Happiness Road", for the 2018 Taiwanese animated film under the same title. In December 2017, she recorded the theme song, "Stand Up", for the 2018 Chinese film, Monster Hunt 2. In January 2018, Tsai released her seventh live album, Play World Tour. In June 2018, Tsai recorded the 10th anniversary theme song, "The Player", for the video game, Dungeon & Fighter.

In November 2014, Tsai released her thirteenth studio album, Play. Tsai commented, "The album refers to film script, acting or performance, which helped me gain wisdom and experiences during the past two years. With the new witty music, I hope my fans will find it playful and joyful as well as bringing optimism to the future." The album garnered critical acclaim and was declared it as "easily the best album of the year". Commercially, the album sold more than 85,000 copies in Taiwan, and became the best-selling album by a female artist of the year in Taiwan. The title track, "Play", reached number one on the Hit FM Top 100 Singles of the Year. The track, "The Third Person and I", reached number eight on the Hit FM Top 100. The music video of "Play" became the most-viewed music video of Taiwan in 2014 and helped thrust her into the international spotlight. Nolan Feeney from Time magazine commented, "It might be the year's best pop music video." She was nominated for an MTV Europe Music Award for Best Taiwanese Act. The album also received ten Golden Melody Award nominations—nine in the 26th Golden Melody Awards and one in the 27th—and eventually won for Best Mandarin Album and Best Vocal Recording Album. In December 2015, she performed the song, "Play", at the 2015 Mnet Asian Music Awards, where she won for Best Asian Artist. In May 2015, she began her Play World Tour, and the show was her first collaboration with Live Nation Entertainment. In October 2015, a worker was killed when the sound, lighting, and video rigging collapsed at a concert that she was planning for at Guangxi Sports Center in Nanning. Tsai expressed sadness on her blog.

Tsai's twelfth studio album, Muse, was released in September 2012. Tsai commented: "The album combines art, pop and music to portray how a girl should act and stand out in modern society." Referred to as a "pop masterpiece", the album received acclaim from critics and sold more than 100,000 copies in Taiwan alone, and became the best-selling album by a female artist of the year in Taiwan. The lead single, "The Great Artist", reached number two on the Hit FM Top 100 Singles of the Year. The track, "Wandering Poet", reached number ten on the Hit FM Top 100. Two more hits, "Dr. Jolin", which reached number twenty-five on the Hit FM Top 100, and "Fantasy" both catered to her gay audience. At the same time, Tsai was nominated for an MTV Europe Music Award for Best Asian Act. Tsai was also nominated for three Golden Melody Awards for Best Mandarin Album, Best Mandarin Female Singer, and Best Music Video for the album, and the lead single, "The Great Artist", won for Song of the Year. In January 2013, she attended the MIDEM in Cannes and performed in Paris at the concert named Taiwan Music Night. In October 2013, she recorded a promotional single, "Journey", which reached number fifteen on the Hit FM Top 100, for the jewelry brand Swarovski. In October 2013, she released her sixth live album, Myself World Tour. In June 2014, ahead of 2014 FIFA World Cup, she recorded an English single, "Now Is the Time", which was included on the compilation album Pepsi Beats of the Beautiful Game, to support the World Cup of the year. In the same month, Tsai recorded the theme song, "Kaleidoscope", for the 2014 Chinese romantic drama film, Tiny Times 3. In October 2014, Tsai became one of the judges for the reality television singing competition, Rising Star, with Harlem Yu, Chris Lee, and Li Jian.

Tsai released her eleventh studio album, Myself, in August 2010. The album is considered among her most adventurous, with almost all tracks are dance songs, which had never previously attempted by any Chinese singer. However, the album received mixed reviews and sold only more than 65,000 copies in Taiwan. It became her lowest-selling studio album of her career to this date in Taiwan, but still became the best-selling album by a female artist of the year in Taiwan. The hit song, "Honey Trap", reached number one on the Hit FM Top 100 Singles of the Year. Two more tracks, "Nothing Left to Say" and "Love Player", reached number twenty and fifty-five on Hit FM Top 100. The music video of "Honey Trap" features the dance moves of vogue in tribute to her icon Madonna. The music video of "Honey Trap" was nominated for a Golden Melody Award for Best Music Video. In December 2010, Tsai embarked on the Myself World Tour. It was a box office success with a gross of NT$150 million from 35 shows. An accident occurred during her rehearsal for the second leg of the tour. Tsai fell during the upside-down pole dance practice after her male dancing partner's hand slipped, which left her with a dislocated spine that led to muscle spasms. Tsai was forced to cancel the pole dance performance, which was originally planned to be performed during the Taipei stop of the tour in December 2012, but she eventually performed the pole dance during the Kaohsiung stop in April 2013. In January 2011, Nokia released a chart of the top 10 songs downloaded globally through its Ovi Music Store in 2010, and Tsai's "Honey Trap" made number nine on the chart. In July 2011, she released her first diet book, Living Slim, and it sold more than 120,000 copies in Taiwan alone.

Having sold more than 25 million records in Asia, Tsai is recognized as one of the best-selling artists in the region. Her works have earned her numerous awards and accolades, including six Golden Melody Awards, an Mnet Asian Music Award, an MTV Asia Award, and an MTV Video Music Award. As a businesswoman, she founded her own entertainment company Eternal in 2009. Her other ventures include fashion design and writing books. Forbes reported that she is one of the highest-paid Chinese celebrities, with the estimated net worth of NT$2 billion in 2014.

In 2009, Tsai and Ken Erman, the founder of the fashion company Truth and Pride, co-founded the fashion brand, Seventy Two Changes, named after her 2003 album Magic (also as known as See My 72 Changes literally in Chinese). The brand consisted of apparel, footwear, and accessories, and was available at department stores in more than 30 cities worldwide. In 2010, Tsai opened the brand's first boutique at Shanghai Times Square in Shanghai. The net profits of the two years was more than US$5 million. However, the business was closed down in 2011 due to the difference of business ideas between shareholders in mainland China and United States.

In December 2008, she signed a recording contract with Warner Music Taiwan. 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; It was closed down in 2011 due to the difference of business ideas between shareholders in mainland China and United States. In March 2009, Tsai released her tenth studio album, Butterfly. Commercially, the album sold more than 1 million copies in Asia, with more than 190,000 copies sold in Taiwan alone, and became the best-selling album of the year in Taiwan. However, media and critics reacted negatively, who commented that the album was a "confusing patchwork". The title track, "Butterfly", reached number ten on the Hit FM Top 100 Singles of the Year. The song, "Real Man", also reached number twenty-five on the Hit FM Top 100. To further promote the album, she embarked on the Butterfly Campus Tour. However, she distorted her right scapula, strained her thigh muscle, and sprained her right ankle due to over-training at the time. In October 2009, she released her fifth live album, Love & Live, which contains the performances from two of her one-off concerts, Butterfly Concert and Slow Life Concert. In October 2009, Tsai extended her business ventures and co-founded her own music production and management company, Eternal, with her manager Ke Fu-hung. In April 2010, Tsai named the ambassador and recorded the theme song, "Heartbeat of Taiwan", for Taiwan Pavilion of Expo 2010.

In June 2007, Tsai's first documentary as well as her fourth live album, If You Think You Can, You Can!, was released. The documentary chronicled her Dancing Forever World Tour. In September 2007, she released her ninth studio album, Agent J. The album was well received by critics and sold more than 2.5 million copies in Asia, with more than 200,000 copies sold in Taiwan alone, and became the best-selling album of the year in Taiwan again. The title track, "Agent J", reached number fourteen on the Hit FM Top 100 Singles of the Year. Two more hits, "Sun Will Never Set" and "Bravo Lover", reached number one and number forty-one on the Hit FM Top 100. Tsai also received an MTV Asia Award nomination for Favorite Artist Taiwan. To accompany the album, she released her debut film, Agent J, and played the title role. She was well received by media and the general public. At the same time, she and her sister premiered Oops! Jealous, a range of nail polish products. In November 2007, she provided a guest vocals on Kylie Minogue's "In My Arms", which was included on the Asia edition of Minogue's album, X. The song reached number twenty-seven on the Hit FM Top 100. In April 2008, she featured the theme song, "Beijing Welcomes You", for the 100-day countdown of the 2008 Summer Olympics. 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 October 2008, Tsai released her first cover album as well as her third English reference book, Love Exercise, which contains her covers of ten English classic songs. The album was scheduled to be released in March 2008, but it was forced to be delayed due to the withdrawal from the entire Greater China market of EMI in early 2008, which was the parent company of Tsai's record label, Capitol. However, Tsai's busy schedule means she wouldn't have as much time for her promotional duties for the album, hence it didn't get any promotion. The album was poorly received by critics but was the best-selling Western-language album of the year in Taiwan, with more than 30,000 copies sold in Taiwan alone. The lead single, "I Won't Last a Day Without You", the cover of the Carpenters song, reached number seven on the Hit FM Top 100 Singles of the Year.

Having a dedicated fanbase composed mostly by female and gay people, Tsai is considered a gay icon. In 2007, Tsai's "Bravo Lover" became the theme song of the 2007 Taiwan Pride parade. Her other songs, including "Fantasy", "Dr. Jolin", "Gentlewoman", "We're All Different, Yet the Same", and "Womxnly", all cater to the gay audience and support same-sex love. In 2012, she signed the petition calling for Taiwan's government passing Marriage Equality Act and legalizing same-sex marriage in Taiwan. Recognized as a long-term ally of the LGBT community, Tsai was given the Icon Award at the 2nd Asia LGBT Milestone Awards to praise her putting aside the pressure of public opinion and appreciate her using her influence to support same-sex love in Chinese-speaking world. In 2015, Tsai featured on the cover of lesbian-themed magazine Lezs. In an interview with Lezs, she spoke about homophobia and advocated people to embrace all kinds of love. She stated, "we have to give them the time to get to understand one another, since the definition of love varies from person to person." During her Play World Tour (2015–2016), Tsai gave a speech to support transgender people, and spoke against the bullying of children and teenagers in general, including the bullying of gay teens and a related recent suicide in Taiwan.

In 2007, Tsai and her sister launched the nail polish brand named Oops! Jealous. With a range of nail polish products, the brand was originally available at the Taiwan's online shopping website PayEasy. In 2009, Tsai's sister and friend opened a nail salon named Oops! J&I in Walnut, California, and the nail polish products were also available at the salon. In 2010, Oops! Jealous collaborated with PayEasy to introduce a vending machine specialized in dispensing cosmetics into the shopping mall Q Square in Taipei. In 2011, the brand was available at the personal care chain store Wastons in Taiwan. In 2014, her sister's nail salon in the United States transferred the ownership to successor.

In February 2006, Tsai signed a recording deal with Capitol Music Taiwan. In May 2006, she debuted her song, "Dancing Diva", at the MTV Asia Awards 2006. Her dance move of rhythmic gymnastics during performing the song stunned the audience. She also won an MTV Asia Award for the Style Award. At the same time, Tsai released her seventh studio album, Dancing Diva, which reflected another big change in her music and image. The album received strong positive reaction from the media and the general public and sold more than 2.5 million copies in Asia, with more than 260,000 copies in Taiwan alone, and became the best-selling album of the year in Taiwan. The tile track, "Dancing Diva", reached number thirty-three on the Hit FM Top 100 Singles of the Year. Two more hit songs, "Pretence" and "A Wonder in Madrid", also reached number three and number fourteen on Hit FM Top 100. The album honored her with two Golden Melody Awards—Best Mandarin Female Singer and Most Popular Female Singer (popular vote)—and was nominated for Best Mandarin Album. "I want to thank the naysayers, your attack made me work harder," Tsai said. "Thank my supporters, what you expect from me has always made me get the best out of myself." However, Tsai's win for Best Mandarin Female Singer generated controversy from critics. The awards jury commented, "She won due to her all-round talent, hard work, and universal pop appeal." In August 2006, Tsai provided a guest vocals on Taiwanese singer David Tao's "Marry Me Today", which reached number one on the Hit FM Top 100 and won for a Golden Melody Award for Song of the Year. Tsai embarked on the Dancing Forever World Tour in September 2006, which continued until 2009. The performances featured her striking yoga poses on rings and pommel horse. However, some critics complained that the show concentrated on "juggling", but generally the response was favorable. At the same time, she release her third remix album, Dancing Forever, which contains Hit FM Top 100 number forty-six hit, "Dancing Forever". In February 2007, she performed the song, "Marry Me Today", with David Tao at the CCTV New Year's Gala.

Tsai has cited her major influences in her music career as being Whitney Houston, Mariah Carey, Destiny's Child, and Madonna. She cited Whitney Houston and Mariah Carey her "two favorite artists" whom she would often sing along to in her childhood. Mariah Carey's "Hero" and Whitney Houston's "Greatest Love of All" were two of the songs she performed in the MTV singing competition and helped her receive the champion. Tsai also cited Destiny's Child major influence in her early music career, and she praised their powerful vocals and dance. Since Dancing Diva (2006), Tsai has drawn comparisons to Madonna in terms of stage presence. Tsai commented that "I have been a huge fan of Madonna. She's the person I've looked up to. I would like to be a star like her." Choreographer Chang Sheng-feng, who collaborated with Tsai since her debut, claimed that she took time to watch Madonna's live performance. Tsai also described that "Madonna's every single dance move was powerful, and that's the stage performance style I'd look up to." 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); The music video of "Honey Trap" from Myself (2010) features vogue in tribute to Madonna. Madonna brought dance music into massive popularity in mainstream music scene, and it was similar to what Tsai would like to do in Greater China. 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." She has also named Janet Jackson, Kylie Minogue, Sandy Lam, Faye Wong, Coco Lee, and A-Mei as sources of inspiration.

Her seventh studio album, J-Game, was released in April 2005. The album received positive critical reception and sold more than 2 million copies in Asia, with more than 260,000 copies sold in Taiwan alone, and became the best-selling album by a female artist of the year in Taiwan. Tsai received an MTV Asia Award nomination for Favorite Artist Taiwan. The title track, "J-Game", reached number twenty-six on the Hit FM Top 100 Singles of the Year. Two more hit tracks, "Sky" and "Overlooking Purposely", reached number two and sixty-five on the Hit FM Top 100. In September 2005, she recorded the Mandarin version of the song, "Under the Sea", from the Disney animated film, The Little Mermaid, to celebrate the grand opening of Hong Kong Disneyland. At the same time, she also released her third live album, J1 Live Concert, which contains the performances from her J1 World Tour. In October 2005, she provided a guest vocals on Taiwanese singer Show Lo's "Destined Guy", which reached number fifty-five on the Hit FM Top 100 and was included on Lo's album, Hypnosis Show. In January 2006, Tsai released her second English reference book, Jolin's Party, which sold more than 1 million copies in Asia, with more than 180,000 copies in Taiwan alone.

In the 2003 television drama, Hi Working Girl, Tsai played the title role of Fu I-ling. After its release, the television drama received mixed reviews. The same year, she graduated from Fu Jen Catholic University and received her bachelor's degree in English literature; She was later elected as a recipient of the Excellent Alumni Award in 2011. In February 2004, Tsai's sixth studio album, Castle, was released. She received positive feedback for the album, and it sold more than 2 million copies in Asia, with more than 300,000 copies sold in Taiwan alone, and became the best-selling album by a female artist of the year in Taiwan. Two hit tracks, "It's Love" and "36 Tricks of Love", reached number eight and seventy-eight on the Hit FM Top 100 Singles of the Year. Tsai received an MTV Asia Award nomination for Favorite Artist Taiwan. She was also nominated for an MTV Video Music Award Japan for Best Buzz Asia for the music video of "Pirates". Beginning in August 2004, Tsai embarked on her first concert tour, J1 World Tour. In December 2004, Tsai released her second remix album, J9, which contains the Hit FM Top 100 number sixty-one hit, "Signature Gesture". In February 2005, she performed "36 Tricks of Love" at the CCTV New Year's Gala. In March 2005, she signed with a contract with publisher YuanShen to be the author of a series of English reference books. The first release of these books, Jolin's English Diary Book, sold more than 1 million copies in Asia, with more than 250,000 copies sold in Taiwan alone.

Tsai possesses a mezzo-soprano vocal range. She emerged champion at an MTV singing competition, and she used a bright, girlish vocal timbre in her early albums. However, she has been criticized in her early years for her vocals due to her limited vocal range. Producer Bing Wang, who collaborated with Tsai on her album Magic (2003), highlighted her tone and timbre as distinctive, but he claimed that "she does not have a gifted vocals." In 2007, Tsai won a Golden Melody Award for Best Mandarin Female Singer, and it was the very first time that her vocals was recognized by professional music awards. However, her win for Best Mandarin Female Singer generated controversy from critics. The awards jury responded that "she won due to her all-round talent and universal pop appeal." Sam Chen, the president of Warner Music Taiwan, commented that she is "not a born vocalist but studied with vocal coaches." Before the recording sessions of almost all of her studio albums, Tsai took vocal lessons, which increased her vocal range. Producer Tiger Chung, who collaborated with Tsai on her album Play, praised her vocal range and power. However, Play failed to earn her a Golden Melody Award nomination for Best Mandarin Female Singer. It raised a controversy among general public, and the awards jury responded that they doubted the overuse of pitch correction in the album's songs. However, Tsai's manager Tom Wang dismissed the rumours, "we welcome those who are in doubt to hear her live performance. I am confident with her ability," he said. Critics Chen Le-jung, after watched her live performance during her Play World Tour, commented that Tsai is "being able to sing long and vocal runs effortlessly".

Known for reinventing her style and image, Tsai's music and fashion sense are noted by the media and general public. Although she was modest in appearance in early years, her image and fashion has changed several times since the release of her fifth studio album, Magic (2003). Around the time of the release of Magic, Japan's Ray magazine named her "Taiwan's trend-setter". However, many critics felt that her style at the time was too similar to those of Japanese singer Ayumi Hamasaki. 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." With the beginning of her first concert tour, J1 World Tour (2004–2006), Tsai mostly dismissed her innocent image for a more sexy look. In 2006, Tsai received an MTV Asia Award for the Style Award. At the same time, Yahoo! Taiwan named her the most stylish artist in Taiwan. 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. Her appearance has landed her on the cover of magazines such as Elle, Harper's Bazaar, Marie Claire, and Vogue. Tsai is also considered a sex symbol. In 2006, FHM Taiwan ranked her fourteenth on the "100 Sexiest Women in the World" list. She also had appeared in the top ten on the list eight times in the subsequent ten years. In 2016, FHM Taiwan ranked her first on the list again.

Tsai was considered a "quality product" in C-pop music industry, and she mostly obeyed the arrangements of her labels for commercial purpose in early years. Since Magic (2003), each of her studio albums at least became the best-selling album by a female artist of the year in Taiwan. Dancing Diva (2006), Agent J (2007), and Butterfly (2009) each even became the best-selling album of the year in Taiwan. Tsai is considered one of the highest-paid Chinese female singers of the 21st century. In 2010, Forbes China began reporting on earnings of Chinese celebrities born in Hong Kong, Taiwan, and abroad. 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. In 2011 and 2012, she ranked fifteenth and seventh on the list with NT$262 million and NT$397 million, made her the second highest-paid Chinese female singer of both years. In 2013 and 2014, she ranked ninth and twentieth on the list with NT$478 million and NT$260 million, made her the highest-paid Chinese female singer of both years. In 2015, she ranked sixteenth on the list with NT$252 million, made her the second highest-paid Chinese female singer of the year. In 2017, due to the declining influence of Chinese music industry, she ranked eighty-third on the list with NT$229 million, but still made her the third highest-paid Chinese female singer of the year. As of December 2014, Tsai's net worth was estimated to be more than NT$2 billion.

Tsai has supported various charitable organizations and causes during her career. In 2003, Tsai and other Taiwanese artists recorded a single titled "Hand in Hand" with the intention to call for fighting against the 2003 SARS outbreak. She then made a visit to Centers for Disease Control of Taiwan to meet with the medical staff and express her thanks to them. At the same time, Tsai joined Ronald McDonald House Charities to support their program to build Ronald McDonald Family Room and improve the well being of sick children in Taiwan. She donated part of the tickets revenue of the Taipei stop of her J1 World Tour to the organization in 2004. She donated an extra NT$10 million to the organization in 2006. In response to the 2004 Indian Ocean earthquake and tsunami, Tsai donated several times anonymously to help the victims of the catastrophe. In 2008, Tsai donated NT$5 million to help the victims of the 2008 Sichuan earthquake. She then joined World Vision and represented the organization to visit the disaster area and express sympathy and solicitude to the victims of the disaster area. In 2009, Tsai donated NT$3 million to help the victims of the typhoon Morakot. In 2010, Tsai donated NT$1.5 million to help the victims of the 2011 Tōhoku earthquake and tsunami. In 2013, Tsai donated NT$5 million to help the victims of the 2013 Lushan earthquake. She then joined Sichuan Charity Federation and donated an extra NT$0.7 million to fund educational programs in the disaster area. In 2014, Tsai donated NT$2 million to help the emergency workers and victims of the 2014 Kaohsiung gas explosions. In 2016, Tsai joined Bazaar Charity Fund Foundation and China Siyuan Foundation for Poverty Alleviation to donate NT$3.5 million to help purchase ambulances for poverty-stricken areas in China. In 2017, Tsai joined Beijing I-db Foundation to donate NT$2 million to help deaf children's rehabilitation. She then joined Huashan Social Welfare Foundation to donate NT$2 million to improve the quality of life of elderly people living alone. In 2018, Tsai donated NT$1 million to help the victims of the 2018 Hualien earthquake. In 2020, Tsai donated NT$4.4 million to Wuhan Charity Federation to help protect against the COVID-19 pandemic.

In July 2002, Tsai signed a recording deal with Sony Music Taiwan, and got one of the biggest transitions in her music career. In August 2002, she made another cameo appearance in the television drama, In Love. In the same month, Tsai released her second photo book, The Masque of the Princess, the Spirit of Knight, with pictures primarily photographed in Thailand. It sold more than 50,000 copies in Taiwan alone. The single, "Spirit of the knight", which she collaborated with Taiwanese singer Jay Chou, was released. Tsai's highly anticipated fifth studio album, Magic, was released in March 2003. The album garnered critical acclaim and sold more than 1.5 million copies in Asia, with more than 360,000 copies sold in Taiwan alone, and became the best-selling album by a female artist of the year in Taiwan. The title track, "Magic", reached number twenty-four on the Hit FM Top 100 Singles of the Year. Two more hit songs, "Say Love You" and "Prague Square", also reached number three and number sixty-five on the Hit FM Top 100. Tsai earned her first two Golden Melody Award nominations for Best Pop Vocal Album and Best Mandarin Female Singer. She was also nominated for an MTV Asia Award for Favorite Artist Taiwan. In April 2003, Tsai sang the theme song for the Hong Kong romantic comedy film, Why Me, Sweetie?!. In September 2003, Tsai helped American singer Madonna translate her children's book, titled The English Roses, into traditional Chinese, as well as successively translated five other Madonna's books since then. In October 2003, Tsai recorded the theme song, "Marage (Warriors in Peace)", which was produced by Indian producer A. R. Rahman, for the Chinese action adventure film, Warriors of Heaven and Earth.

In June 2001, she recorded the Mandarin version of the theme song, "Where the Dream Takes You", for the 2001 Disney science fiction film, Atlantis: The Lost Empire. The song was included on the pre-order edition of Tsai's fourth studio album, Lucky Number, which was released in July 2001. Tsai received mixed reviews for the album, and it only sold more than 150,000 copies in Taiwan alone. The track, "If You Don't Want", reached number ninety-four on the Hit FM Top 100 Singles of the Year. Just after she released the album, Tsai's music career came to a halt due to the conflict with her management company of the time, D Sound. Tsai's father sued D Sound and claimed inappropriate contents in her recording contract and poor bookkeeping in the company. The dispute was resolved when Tsai paid NT$9 million in liquidated damages to D Sound. In December 2001, Tsai made a cameo appearance in the television drama, Six Friends. In March 2002, Tsai made a cameo appearance in the television drama, Come to My Place.

Tsai was rumored to have a relationship with Taiwanese singer Jay Chou after their collaboration on "Can't Speak Clearly", which appeared on her fourth studio album Lucky Number (2001). In December 2001, Tsai and Chou were first spotted dining at an izakaya in Shinjuku, Japan. Although they did not admit to their relationship, their romance was an open secret in those years. However, in February 2005, Chou was spotted shopping intimately with Taiwanese news presenter Patty Hou in Shibuya, Japan. Since then, Tsai deliberately avoided meeting Chou and Hou during public events. In June 2010, Tsai and Chou finally made amends, and Tsai appeared as a special guest at Chou's concert in Taipei and shocked the public. In July 2013, when being interviewed by Taiwanese TV host Matilda Tao, for the first time, Tsai admitted she used to be in love with Chou. In addition, Tsai said that since Chou cheated on her, she felt disappointed and broke up with Chou. In January 2007, Tsai and Taiwanese actor Eddie Peng were spotted shopping in a mall in London. In September 2008, Peng had a conflict with his management company of the time, Power Generation, and the reason was believed to be the company tried to interrupt his affair with Tsai and then led them to break up. In August 2009, Peng's former manager Liu Wei-tzu confirmed they tried to interrupt Tsai and Peng's relationship, and she also confirmed that they started a relationship in mid 2006 and it lasted three years. In July 2010, New Zealand model Vivian Dawson featured in the music video of Tsai's "Love Player". In September 2010, Tsai and Dawson were spotted on a date in Tokyo. In February 2013, Dawson took Tsai to visit his parents and relatives in New Zealand, and their relationship was believed to be settled. In December 2016, Tsai's manager Tom Wang confirmed Tsai and Dawson parted amicably in November and remain close friends.

In May 2000, Tsai released her first photo book, Nineteen Years, with pictures primarily photographed in Hawaii, and it sold more than 60,000 copies in Taiwan alone. In December 2000, Tsai released her third studio album, Show Your Love, which her voice in the album was considered more mature and soothing. However, it was poorly received by such critics as Taiwanese singer Sandee Chan, who commented that "It was done intentionally. Having a good voice doesn't always mean making a good album." The album sold more than 260,000 copies in Taiwan alone. The hit singles, "Do You Still Love Me" Reached number thirty on the Hit FM Top 100 Singles of the Year. In March 2001, she released her second live album, Show Your Love Concert. In the same month, Tsai performed the title track, "Show Your Love", at the Japan music program broadcast Asia Super Live in Tokyo by Japan television station Fuji Television. Tsai won an MTV Video Music Award for International Viewer's Choice for the music video of "Fall in Love with a Street".

Tsai has sold more than 25 million albums in Asia, and is recognized as one of the best-selling artist in Asia. Due to the adverse impact from the copyright infringement and Internet downloads in Greater China since the 2000s, Chinese recording artists have experienced losses and decrease in sales. However, since her album Magic (2003), each of her studio albums at least became the best-selling album by a female artist of the year in Taiwan. Three albums—Dancing Diva (2006), Agent J (2007), and Butterfly (2009)—each even became the best-selling album of the year in Taiwan. Tsai has 39 songs listed on the Hit FM Top 100 Singles of the Year, the Taiwan's equivalent to the Billboard Year-End Hot 100. With five songs—"Marry Me Today", "Sun Will Never Set", "Honey Trap", "Play", and "Ugly Beauty"—topping the chart, she became the singer with the most number-one songs on the chart. Tsai has been honored with numerous awards and nominations domestically and internationally, including an MTV Video Music Award for International Viewer's Choice, an MTV Asia Award for the Style Award, an Mnet Asian Music Award for Best Asian Artist. She has also won six Golden Melody Awards, the most equivalent to the Grammy Awards in Greater China, and made her the dance-pop singer with the most Golden Melody Award trophies received. In 2016, her album Play set the record for the most Golden Melody Awards nominations (ten nominations), leading to a tie with Taiwanese singers Jay Chou's Fantasy (2001) and A-Mei's Amit (2009).

After Tsai signed a recording deal with Universal, her debut single, "Living with the World", was released in July 1999. She then started developing her debut album, 1019, which was released in September 1999, and she received positive feedback for the album, with 400,000 copies sold in Taiwan alone. Tsai was named as the "Teenage Boy Killer" by media, and became an instant hit among teenagers in Taiwan. The lead single, "I Know You're Feeling Blue", reached number thirty on the Hit FM Top 100 Singles of the Year. In March 2000, she released her first live album, 1019 I Can Concert. Tsai achieved general recognition in Greater China after the release of her second studio album, Don't Stop, in April 2000. The album became her best-selling album in Taiwan of her career to this date with sales of 450,000 in Taiwan alone. The title track, "Don't Stop", reached number fourteen on the Hit FM Top 100 Singles of the Year.

Born and raised in Taiwan, Tsai began her singing career by winning the champion at an MTV singing competition in 1998. Her debut album, 1019 (1999), made her quickly become a teen idol with a large teenage fanbase. Her fifth album, Magic (2003), is regarded as one of her biggest successes so far, right after her eighth album, Dancing Diva (2006), which reflected her mature artistic statement. Her thirteenth album, Play (2014), further thrust her into the international spotlight. After several successful albums, her fourteenth album, Ugly Beauty, was released in 2018.

In 1998, Tsai joined an MTV singing competition for a record of an extracurricular activity she performed in order to help her apply for colleges. However, she emerged champion at the singing competition where she sang a rendition of Whitney Houston's "Greatest Love of All" in the final round. It was an accidental win that kickstarted her singing career and paved the way to her journey in becoming a teen idol. In 1999, she majored in English literature at Fu Jen Catholic University, and signed a recording deal with Universal Music Taiwan.

Jolin Tsai (/t s ˈ aɪ / ; Chinese: 蔡依林 ; born September 15, 1980) is a Taiwanese singer, songwriter, dancer, actress, and businesswoman. Tsai is known for frequently reinventing both her music and image, and she is cited as a huge role of popularizing dance-pop as mainstream popular music in Greater China. She maintains her autonomy within the recording industry, and her musical productions have received widespread critical acclaim. Referred to as the "Queen of C-Pop", she has achieved popularity in Chinese-speaking world by releasing a series of successful albums.

Tsai was born to parents Tsai Chu-chen and Huang Chun-mei in Hsinchuang, Taipei, Taiwan, on September 15, 1980. Her father is of Han Chinese descent, while her mother is half Han Chinese and half Papora. Her Papora maternal grandmother hails from Puli, Nantou, Taiwan. She attended Hsinchuang Elementary School. Tsai was known for her high grades, and frequently achieved top 3 in class since elementary school. Tsai was a 200-meter sprinter in elementary school, but quit after she injured her ankle. Tsai later attended Hsinchuang Junior High School and Chingmei Girls' High School where she and her friends formed a band Twister for which she sang, but the band quickly dissolved. In the second year of high school, she made her performance debut on campus, and sang the Cranberries's "Zombie" at the welcome party of the school's pop music association. In a different campus event, she sang Bette Midler's "The Rose", and was buoyed up by the enthusiastic reception her audience gave her.