The year 1999 was somewhat of a breakthrough for Yu, as he took the lead role in Jang Jin's acclaimed cult comedy, The Spy and also starred in Kim Sang-jin's hugely successful Attack the Gas Station.

Appearing as Jang Dong-gun's co-star in Kwak Kyung-taek's smash hit Friend, which sold an unprecedented 8 million tickets, Yu won effusive critical praise for his hard-edged performance as a ruthless gangster and enjoyed a tremendous degree of exposure.

[3] Yu's next two films, the melodrama Star with actress Park Jin-hee and the patriotic/historical drama Thomas An Jung-geun about the titular independence activist, bombed badly at the box office.

Set in the Joseon period during the reign of King Sukjong, Jang Gil-san was born of a female servant, raised by gypsies, then rises politically.

His performance as Choi Won-sin, a villainous and powerful merchant and the archenemy of Lee Joon-gi's character, was widely praised and earned him a nomination for Best Supporting Actor at the 2014 KBS Drama Awards.