His first brush with fame came in the role of "Paint" in his second feature, the 1999 hit "Attack the Gas Station". His sensitive and artistic image in this film and the warm character he displayed as a guest on TV talk shows helped to propel him to stardom. With the surprise success of his third film "Ditto" in spring 2000, Yoo's star status was secured. He also appeared in the successful firefighting film "Libera Me". In this early part of his career, he was known particularly for the wild colors that he would dye his hair (white in "Attack the Gas Station", blue in "Ditto", blonde in "Libera Me").