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Yoo began directing short films in 2003, which were well received in the film festival circuit.His feature directorial debut Mai Ratima was released in 2013.
In 2001, however, he dyed his hair black and took on a more subdued, serious role in Hur Jin-ho's One Fine Spring Day.
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.
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.