Ahn Jae-wook made his acting debut in 1994 through the two-episode MBC drama Song of a Blind Bird. In 1996, he appeared in another MBC series called Love and War, which won him Best New Actor at the 32nd Baeksang Arts Awards. In 1997, he was launched into Hallyu stardom after starring in the high-rating MBC series Star in My Heart. In 1998, he took home the Best New Actor trophy at the 19th Blue Dragon Film Awards for Tie a Yellow Ribbon. In 2004, he led the KBS2 series Oh Feel Young, which earned him a Top Excellence Award at the KBS Drama Awards. In 2016, he played a widower in the KBS2 family drama Five Kids, which scored him an Excellence Award at the KBS Drama Awards.

Aside from acting, Ahn Jae-wook has also established a successful singing career. He released his debut album titled Forever in 1997. This was followed by several more album releases and concerts over the years.

Ahn Jae-wook studied theater at the Seoul Institute of the Arts. In 2013, he underwent an operation for a subarachnoid hemorrhage in his brain in the U.S. In 2015, he tied the knot with theater actress Choi Hyun-joo. They met in 2014 through the musical Rudolf, where they played as lovers.