He debuted in South Korea in 1997 with the song "Gawi" and became one of the country's most popular K-pop stars at the time.

[8] He is best known for his roles as Jin Wuzhu in 2013 historical TV series The Patriot Yue Fei and Prince Wen in 2010 film Little Big Soldier.

[10] Yoo led a troubled life during his teen years until he joined the church choir, where he found a passion for singing.

[9] He made demo tapes of his rapping and dance skills and sent these to Brothers Entertainment, where he was eventually scouted and left California to start his career as a singer.

In 2000, he began to expand his career into China and Taiwan, with the release of the single "Can't Wait", which was a collaboration with Taiwanese singer Yuki.

[13][14] The album was produced under the collaboration of production teams from the United States, China, and South Korea.

In June 2008, Yoo signed a 15-year contract with Jackie Chan's entertainment management company to become an actor.

[16] In February 2010, Yoo made his film debut in Jackie Chan's Little Big Soldier as Prince Wen.

[citation needed] On November 21, 2018, Yoo attempted to make a comeback in the Korean entertainment industry with a 5-track extended play album titled Another Day originally set for release on December 5, with the pre-release title song "Another Day" and accompanying music video set to release on November 22.

[citation needed] After his banishment from South Korea in 2002, Yoo made his residence in Beijing, China.

In October 2019, Yoo launched his YouTube channel, where he posted videos of his daily workout routine.

While Yoo was in South Korea, he attended Kaywon School of Art and Design as a multimedia major.

In 2010, when he was invited as a guest on the show Asia Uncut, he stated he (at the time of filming) held a 3rd Dan black belt.

[7] Yoo had attempted to return to South Korea in February 2002 to resume his activities and to hold a press conference regarding his citizenship, but he was banned from entering the Incheon International Airport.

[24] On May 19, 2015, Yoo held a live stream through AfreecaTV apologizing to the Korean public and addressing his reasons for pursuing citizenship in the United States.

[26] In 2020, Mo Jung-hwa, the chief of the Military Manpower Administration, stated that Yoo appearing on South Korean broadcasts as a figure in the entertainment industry would create a "risk of lowering the morale" of South Korean citizens performing military service and affect their "willingness" to fulfill their duties.

[37][38] Following this, Yoo attempted to apply for a visa again, but the Consulate General of Los Angeles again rejected the application on July 2, 2019, causing him to file a second lawsuit with the Seoul Administrative Court in October 2020.

[42] On November 30, 2023, the Seoul High Court ruled in favor of Yoo, stating that there was "no just cause" to deny him a visa.

[29] However, the court ruling was separate from the South Korean government's ban, and Yoo attaining a visa did not indicate he would be allowed back into the country.