Rooftop Prince mengisahkan tentang Putera Raja Tae Mu dari Dinasti Joseon yang baru kehilangan isterinya Tiba-tiba masuk ke abad 21 dan bertemu dengan wanita yang mirip isterinya Se Na.
Tae-mu (Lee Tae-sung), after killing his lost cousin in the United States, returns to Korea, claiming that his cousin, Tae-yong (Park Yoochun), could not be found in New York City. Meanwhile, Tae-mu has been having a secret affair with Se-na (Jeong Yu-mi), his secretary, who, in turn, runs into her long-lost stepsister Park-ha (Han Ji-min). Park-ha has been missing for a prolonged period of time and it is revealed that she was in the US after Se-na abandoned her on the streets at age 9.
Two years after Tae-yong's disappearance, four men dressed in Joseon era garments, fall onto Park-ha's rooftop house. Hungry, homeless and having nowhere to go, the four men decide to stick with Park-ha. Their leader, Lee-gak claims that he is the Crown Prince of Joseon (Park Yoochun), along with his entourage - scholar Song Man-bo (Lee Min-ho), personal bodyguard Woo Yong-sool (Jung Suk-won), and palace eunuch Do Chi-san (Choi Woo-shik). One day, Crown Prince Lee Gak sees Se-na who is the spitting image of his beloved wife, who was found drowned in the 18th century. He is convinced she is his wife's reincarnation. Meanwhile, company president Yeo (Ban Hyo-jung) mistakes Lee Gak for her grandson, Yong Tae-yong, because of their exact same appearance, and believes that her long lost grandson had finally returned. Lee Gak realizes that he hastime traveled 300 years to 2012, Seoul, to search for the truth behind the mysterious death of the late Crown Princess. In order to approach Se-na, who is also President Yeo's personal assistant, Lee Gak pretends that he is Tae-yong. Tae-mu, believing that he already killed his cousin in New York, lives in constant fear of his devious act being discovered by the family and "Tae-yong" (aka Lee Gak) who claims not to have remembered the event. Tae-mu has always been jealous of Tae-yong's favored position in the family.
On the other hand, Park-ha is shocked by the news that her new friend who calls himself the Crown Prince is, in fact, the grandson of the CEO. But before long, her feelings for Lee Gak blossom and she is hurt when she finds out that Lee Gak, who still holds very tender memories of his dead wife, is courting Se-na. Lee Gak also believes that marrying Se-na in Seoul year 2012 would bring him closer to solving the mystery of the Crown Princess' murder in the Joseon era.
- Park Yoochun as Prince Lee Gak / Yong Tae-yong
He is the Crown Prince in the Joseon era. Intelligent, kind, wise, cautious and exercises good judgment though a little pompous and prone to think highly of himself (as expected of being part of the Royal Family), the Crown Prince finds himself time travelling 300 years into the future and confronts considerable challenges as he adapts to 21st century Seoul and Park-ha. His modern era counterpart, Tae-yong, was left for dead by his cousin Tae-mu, after the latter pushed the former at the sea at the start of the episode. Lee Gak starts to impersonate as Tae-yong as he realizes that the Joseon era and the modern era holds similarities that will bring him closer to solve his wife's death. (Lee Gak in initial episodes wears a red tracksuit.)
- Han Ji-min as Park-ha / Hong Bu-yong
Strong, resilient and having an optimistic personality, Park-ha has endured many hardships and trials since she was separated from her family at age 9. She has been looking out for herself ever since. She helps Lee Gak and his entourage to live in the modern era after they appeared at her home. Her Joseon era counterpart, Bu-yong, is shy, elegant and smart younger sister of the Crown Princess Hwa-yong who harbors strong feelings towards the Crown Prince. She was to be the supposed betrothed of Lee Gak, until her face was burned accidentally by Hwa-yong and thus the prospect of being the Crown Princess was passed to her older sister and forced herself to wear a face mask to hide the scar on her cheek.
- Jeong Yu-mi as Hong Se-na / Hong Hwa-yong
Se-na is Park-ha's gorgeous older stepsister. She works as the secretary at the company owned by Tae-yong and Tae-mu's grandmother. Ambitious, intelligent, scheming and vengeful, she has relied on Tae-mu in the past to advance herself. She loathes Park-ha and has done many things to make her sister's life difficult. As Hwa-yong, she is Lee Gak's wife, the Crown Princess, and Bu-yong's older sister.
- Lee Tae-sung as Yong Tae-mu / Prince Muchang
Tae-yong's cousin and Se-na's secret lover. He holds a high position in the company and is not lacking in skills nor industry. But because of his father's transgression with another woman, there is no blood relation between Tae-yong's grandmother, who is also the CEO of the company. As a result, Tae-mu has always been sidestepped in favor of Tae-yong. Smart and ruthless, he resorts to whatever means necessary to get what he wants. His Joseon era counterpart (as revealed in the last episode), Prince Muchang, is Lee Gak's half-brother.
- Lee Min-ho as Song Man-bo
One of Lee Gak's entourage. A child prodigy, he has become proficient in all fields of study by age 22. However, because he is an illegitimate child, he cannot sit for any government exams and thus, cannot take a position as officer. Because of the hopelessness of his future prospects, he has abandoned the study of the classics for an immoral lifestyle until Crown Prince Lee Gak enlisted his help to solve the Crown Princess' murder. (In the initial episodes, he wears the green tracksuit.)
- Jung Suk-won as Woo Yong-sool
One of Lee Gak's entourage. He murdered the nobleman who killed his mother and raped his sister, as well as the nobleman's guard of about 15 others. He is very skilled with the sword. When later questioned by Lee Gak, he said that he learned to fight in order to protect the innocent, his nation and his king. His intentions are true and the Crown Prince saved him from the executioner's axe and appointed him as his personal bodyguard. (In the initial episodes, he wears the blue tracksuit.)
- Choi Woo-shik as Do Chi-san
One of Lee Gak's entourage. Smooth with the ladies and skilled with men, Chi-san works at the largest brothel in Joseon. From the palace to the bedroom, Chi-san is wise in the ways of the world. Lee Gak appointed him as palace eunuch to discover what the people are saying about the Crown Princess' murder. (In the initial episodes, he wears the yellow tracksuit.)
- Kim Yoo-suk as the King, Lee Gak's father
- Choi Won-hong as Young Lee Gak
- Jeon Min-seo as Young Bu-yong / Young Park-ha
- Kim So-hyun as Young Hwa-yong / Young Se-na
- Gil Yong-woo as Lord Hong Man-pil, Bu-yong and Hwa-yong's father and Left State Minister of Joseon.
- Kyeon Mi-ri as Lady Jeong, Bu-yong and Hwa-yong's mother.
- Song Ok-sook as Gong Man-ok, Se-na's mother
- Maeng Sang-hoon as Park In-cheol, Park-ha's father
- Kim Hyung-bum as Officer Hong Nak-hyeon, Bu-yong and Hwa-yong's brother and head of the royal police
- Kang Byul as Lady Mimi
- Guzal Tursunova as Becky
- Ban Hyo-jung as Chairman Yeo, chairman of the Home & Shopping Network, and Tae-yong's grandmother
- Ahn Suk-hwan as Yong Dong-man, Tae-mu's father
- Park Joon-geum as Yong Seol-hee, Dong-man's aunt
- Lee Moon-sik as Pyo Taek-soo
- Na Young-hee as President Jang
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