On December 1, 2005, she made her solo debut with the single album "Get Up" and performed the title song, "Get Up", on the TV program Music Bank. A year later, in 2006, she was added in the hip-hop group Uptown, replacing their original vocalist, Yoonmirae, and they debuted on May 25 with the studio album Testimony. On January 15, 2009, Jessi released her first digital single, "The Rebirth".
She then took a break from music and returned to the United States. On July 17, 2014, after a five-year hiatus, Jessi debuted as a part of the hip-hop trio Lucky J, under YMC Entertainment. From January to March 2015, she participated in the first season of Unpretty Rapstar.
In 2016, Jessi was a member of the first season of the variety show Sister's Slam Dunk and its group Unnies. The project group released their first single on July 1, 2016. On July 13, 2017, Jessi released her first mini album, Un2verse.
A year later, on July 6, 2018, she released her sixth and last digital single under YMC Entertainment, "Down". On January 24, 2019, she signed with PSY's new agency, P NATION. Her first release under the agency was the single "Who Dat B" on September 23.
On November 1, she released the single "Drip" which featured Jay Park. On July 30, 2020, Jessi released her second mini album Nuna with "Nunu Nana" as the title track. On the June 20 episode of ', Lee Hyori revealed she wanted to form her dream girl group consisting of herself, Uhm Jung Hwa, Hwa Sa, and Jessi.
On July 30, it was confirmed the four would be holding their first meeting to discuss on the project. The project group, Refund Sisters, debuted on October 10 with their first single "Don't Touch Me". Under the group, Jessi's official stage name was Eun Bi.
On July 6, 2022, P NATION announced Jessi's departure from the agency after her three-year contract had expired and she decided not to renew it. On April 14, 2023, it was revealed that she had signed an exclusive contract with Jay Park's record label MORE VISION. On January 31, 2024, MORE VISION announced that Jessi had departed from the agency after deciding to terminate her exclusive contract.
On September 20, Jessi established her own independent label, UNNI, under entertainment company DOD. On October 18, DOD announced their decision to terminate Jessi's exclusive contract. On June 23, 2025, Jessi announced that her comeback after a long hiatus would take place on June 27.
The next day, she announced her new digital single "Newsflash". On November 9, she announced her third mini album, P. M.
S. , set for release on November 12.
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