Yoon Eun Hye entered the entertainment industry in 1999. Yoon performed her first major role in a drama, Goong as Shin Chae-gyung. This role propelled her to stardom. She portrayed as a tough girl named Han Su in her first movie, Escaping from Charisma. Her next drama after Goong was a comedy called The Vineyard Man Yoon Eun Hye was the lead star of The 1st Shop of Coffee Prince portraying a male role in the drama. Criticisms arose after the first episode aired, but then she proved her acting capabilities even before the drama ended. In line with this, different companies were eyeing her as their endorser due to her gained popularity.