The Legendary Courtesan Hwang Jin Yi (2007)

Done around the same time period, 2006-2007, both shows are different retellings of Hwang Jin Yi. If you want to focus more on Hwang Jin Yi's talent as a gisaeng, as well as colorful costumes, then you might want to watch the T.V. series. If you want to watch a depiction much closer to her real life (according to some people), you can watch the movie. It's good if you watch both though, as both shows depict two different views of the modern world on the historical Hwang Ji Ni and the impact of her charms and talents to the modern world.

These films tell the stories of legendary women who used their beauty, wits and intelligence to get by in a world that wasn't always kind to women, especially those of low-birth and in particular giseangs. One will end more optimistically than the other. Watch to find out which.

It's a movie and adds a totally different take on the life of the famous courtesan.

Before actor Ryu Seung Ryong became popular with Miracle Cell No. 7 and Kingdom Netflix series. I have seen his great performances as a villain in these two shows that has a gisaeng as an important character.
(Bonus: As a result, while most people are surprised that the kind but imprisoned father in Miracle Cell 7 is the same guy in Kingdom, I am actually surprised that he could pull off a kind character in Miracle Cell 7 after seeing his villainy in these 2 shows).
These are the similarities of the 2 shows:
1. Both shows have a gisaeng as an important character (though the gisaeng in Painter of the Wind is not the main character)
2. Both gisaengs are beautiful and is the most desirable gisaeng in the land
3. The main villain in both shows is a much older official played very well by actor Ryu Seung Ryong, who lusts after the gisaeng. He was able to own the gisaeng as a property.
4. Because the gisaeng loves another "man", Ryu Seung Ryong's character wants to get rid of that "man".
5. The "man" the gisaeng loves in both shows are very talented in their own field (the one in Painter of the Wind is good at painting, the one is Hwang Jin Yi is good in martial arts)

Both depicts a story of a woman who was born a noble yet circumstances in her life led her to be linked with a much older man (an official who owns her as a gisaeng in Hwang Jin Yi, a professional painter who became her trainer in Portrait of a Beauty). Both women are very talented, either as a poet or as a painter. Both older men are very much attracted to the young woman linked to them. Despite the older men's attraction, both young women fell in love with a man closer to their age who basically has a low position in Joseon's class based hierarchy. The love triangle in both these shows are then lead to chaos on the three main characters' lives until the ending.

Both movies feature tragic love stories of childhood friends. Each story will tear at your heart, but are nevertheless worth the watch.

Set in 1398. Kim Min Jae is the supreme commander of the Joseon Dynasty. He falls in love for the first time and for that woman he takes risks.
Yi Bang Won is the King’s son. He helped his father set up the Joseon Dynasty era, but he was not picked as the Crown Prince. He still holds ambitions of becoming the King one day.
Jin is Kim Min Jae’s son and the King’s son-in-law. Due to his position as the King’s son-in-law, he is unable to take part in politics and only seeks out pleasure.

The New Yoshiwara pleasure district, in the twilight years of the Edo Period. Popular prostitute Asagiri will soon be freed from her indentured service. One day at a local festival, she meets young artisan Hanjiro who changes her destiny. Asagiri feels love for the first time in her life, but the history involving Hanjiro's client leads to tragic circumstances.