Park Wan is a translator who is constantly pulled by her mother, Jang Nan Hee, to hang out with her elder friend, Jo Hee Ja, Moon Jung Ah, Oh Choong Nam, and Lee Yeong Won. The plot revolves around the friends' twilight years as they rediscovering themselves through relationships and family, the struggles they face due to their old age, and their life journey that they share with Park Wan in the hope she would write a novel about them.
At the height of the 16th-century Chosun Dynasty, a pair of rural male actors - boisterous, macho Jang Seng and quiet, feminine Gong Gil - travels to Seoul and team up with a struggling acting troupe. When their irreverent show, complete with enough bawdy humor and gender-bending to make a contemporary audience blush, mocks the famously hedonistic king, they get more than they bargained for. After being promptly arrested, they're given a chance to spare themselves if they can make the king laugh. To everyone's surprise, the ecstatic monarch loves the show and names the actors official court jesters, giving them more extravagant food and shelter than they'd ever imagined. But the king's attentiveness to Gong Gil makes it quickly apparent that humour isn't the only thing motivating his generosity. The king's mistress, the country's ministers and Jang Seng soon grow suspicious, and jealousy and anger spring from all sides.