After graduating in 1994, Ahn made his acting debut in Song of a Blind Bird, which was based on a real-life story, followed by supporting roles in several 1995–96 television series such as Hotel and Their Embrace.

It not only ignited trends in hairstyle, fashion and products featured in the series,[2] Ahn also became a Korean Wave star, extending his popularity to China, Japan and Southeast Asian countries.

Forever, which was featured in the series' ending during the concert of his character Kang Min, sold over 700,000 copies, and became the title song of his debut album.

[4] He continued to compose and sing over the years, holding numerous concerts in Japan and China, and releasing albums such as Memories and Reds in Ahn Jae-wook.

In 1998, he played lead roles in three films – Rub Love with Lee Ji-eun, Tie a Yellow Ribbon with Kim Hye-soo, and First Kiss with Choi Ji-woo—but did not meet with box office success despite his popularity at the time.

[12] Ahn then played the title role in the 2012 Korean staging of Rudolf, a musical about the 1889 Mayerling Incident involving the Crown Prince of Austria.