At an early age Jessi (short for Jessica) dreamed of becoming a make-up artist or fashion designer. It was her schoolteacher who recognized her musical voice and she changed her mind to become a singer thereafter.
When she arrived in Seoul from the United States she was a member of Korean hip hop and R&B group Uptown. Jessi created some controversy when she insulted K-pop star BoA on Myspace in the summer of 2006.
Although the messages were sent to personal friends, they were leaked out to various Internet forums.
For some time Jessi was inactive in the Korean entertainment industry, as Uptown has gone on a hiatus as well. Uptown (업타운) is a South Korean hip hop and R&B group which first debuted in 1997. Uptown was first created in 1996 when the R&B and hip-hop genres of pop music were first introduced to Korea.
After listening to UpTown songs and some of her singles, she seems to be very talented and like her tonality of her voice.
In 2003 Jessi successfully auditioned for Doremi media and moved to Korea aged 15. In 2005, she i released her first single album Get Up.
In 2006, she was featured in the album Testimony by Uptown. In 2009, Jessi released her second single album The Rebirth. However, in the summer of 2006, screenshots from her MySpace account insulting the popular soloist BoA were released. As aforementioned this led to her five-year hiatus from the kpop industry.
In 2013 Jessica H.O. returned with fresh controversy as news about an alleged assault surface.
In 2014 Jessi returned as a member of Lucky J with rapper J’Kyun and vocalist J-Yo.
That year, Lucky J released the digital single "Can You Hear Me?" On Dec. 31, 2014 Jessi did a collaboration stage with labelmate Ailee and Sistar member Hyolyn. The trio performed the song Bang Bang at MBC Gayo Daejejeon, with Jessi doing the rap verse.
In 2015, Jessi was part of the variety show Unpretty Rapstar, a spin-off of the program Show Me The Money. Unpretty Rapstar is a female rappers survival program. The show consists of a single-elimination competition through rap performances. Jessi was the first runner up in the show.
Jessi featured in JYP's track "Who’s Your Mama?" and its music video, which were released in April 2015. She was also a guest on various popular South Korean variety shows, including Running Man and Happy Together. Jessi released the digital single, "SSENUNNI" on September 15.
In 2016, Jessi was a guest on Please Take Care of My Refrigerator for two episodes in March with fellow singer Hyun-A, during which she elicited a wide range of responses from the cast with her "Ajima-style" Korean peppered with native English observations about the flavors of the dishes created in 15 minutes by the assembled chefs.
In a touching surprise moment, Jessi's mother appeared by video to request that the chefs prepare her daughter food from healthy ingredients that she doesn't like, as she only gets to cook for Jessi once per year as they live in different countries.
There were several opportunities for Jessi to show off her powerful singing voice, most notably when her new music video Excessive Love (살찐 사랑) was shown during the closing credits.
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