The Painter of the Wind (2008)

> Both dramas main female characters love painting.
> Kim Yoo Jung is in both dramas (she's the child version of Moon Geun Young in Painter of the Wind)
> Jang Tae Yoo is director of both dramas
==> expect some lucious paintings for Hong Chun Gi/Lovers of the Red Sky as they were depicted well in Painter of the Wind.
> Some instrumentals from Painter of the Wind also feature in Hong Chun Gi/Lovers of the Red Sky
> Trivia: Hong Chun Gi/Lovers of the Red Sky is the reunion between Jang Tae Yoo and Kim Yoo Jung 13 years after Painter of the Wind.
(PS: Painter of the Wind deserves a rating higher than 7.8, if this is a post 2016 drama, it would have gotten a higher score, at least 8.5).

Both based on the same novel, both entertained the possibility of historical Korean painter Shin Yun Bok as a woman pretending to be a man because her paintings mainly depict women. The two stories interpret the story of Shin Yun Bok being a real woman quite differently, but the similarity in both shows is that the historical character Kim Hong Do(who was a fellow painter of Shin Yun Bok in Joseon era) is her teacher and is also one of the 2 characters who fell in love with her. Both shows depict Shin Yun Bok's life as a woman loved by 2 very different people while living her life as a painter.

Similarities:
=> Story of female characters doing all what they can to thrive in the art form they chose
=> There is implied lesbian relationship in both dramas between the female lead and another female character

They are both based on the same novel, but I think Painter of the Wind does it better.

There are so many similiarities in both dramas:
=> set in the time of King Jeongjo
=> Female lead has to pretend to be a man in order to live well in a patriarchal society.
=> Female lead has sort of a brother character who is much weaker and less talented than her, but the brother character still deeply cares for her
=> Female leads unique talents has led her to enter a male-only institution where she could prove her talents
=> There is a male character in the institution who is a rival for the female's talents.
=> Because of female's talents, she was able to prove herself in the institution she joined with even the King Jeogjo character acknowledging her skills.
=> One of the paintings in Painter of the Wind is a design on the clothes of the most flamboyant male character in Sungkyunkwan Scandal
=> Female lead is an orphan, her father's death is related to his work on King Jeongjo's father Crown Prince Sado
=> A gisaeng is in love with the female lead's male persona (watch the dramas to see if either female lead returns the gisaeng's love)
=> A lot of shenanigans involved, including the female leads having to dress as a gisaeng while in her male persona!
=> One of the villains of both shows has an assassin that was assigned to kill one of the good characters.
=> Considering the setting of both dramas is with the same King Jeongjo, the ending of one drama might make you think why is it not possible for the other drama.
Differences:
=> There is no similar version of Yoo Ah In or Song Joong Ki's characters in Painter of the Wind
=> The teacher and the main male love interest in Sungkyunkwan Scandal are different characters whereas they are the same character in Painter of the Wind
=> Sungkyunkwan Scandal focuses on lessons, books and Confucian teachings while Painter of the Wind's focus on painting.

- Cross dressing sageuk
- Female lead pretends to be a male in order to survive
- Forced to pretend since child due to decision by other people

If you wish to watch a more interesting take on this certain timeline in Joseon history, better watch YiSan. Both dramas have something to do with the arts (painting) and the mystery of the death of Prince Sado.

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.

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 are Joseon period dramas about a woman's struggles to become a great artist. I really love both dramas because both plots explain the characters very well through the use of their art forms. Both dramas also feature a beautiful and talented gisaeng played by two great actresses (though the gisaeng in Painter of the Wind is NOT the lead female). A scene I find quite similar in both dramas is both feature a scene wherein the gisaeng is playing the gayageum instrument while her lover (in Painter of the Wind, this lover is the female lead) is painting as the lover listens to her music.

Both centered on female power.

WWW about 3 career women working with Search Engines;
ThePainterOfTheWind about a female painter who dresses up as a boy in Joseon era and is a better painter than any of the boys.
Both have a bit of romance too.

Fang Jia Hua is the successor of a business. His dream is to open a chocolate store and be an expert in chocolate. He ends up leaving his business and his family to fulfill his dream. Hong Xi En is someone who spent her days slogging and taking up part time work. One day, she ends up working for him and above all, she has to dress herself as a man for the job.

Both are historical romance dramas based on novel written by the same author

Shows are not similar except that Moon Geun Young is the lead in both shows.

However, I am doing this recommendation since I want more people to watch Painter of the Wind as it is a very underrated drama yet an extremely good drama. To understand how good this drama is, first of all the director is Jang Tae Yoo (who also directed another great drama in Tree with Deep Roots plus My Love from the Star and Lovers of the Red Sky). The direction he did in this drama is really good. Second, lead actress Moon Geun Young (who I noticed Catch the Ghost fans sometimes find annoying) won a Daesang in Painter of the Wind. Watch Painter of the Wind to understand how great her performance is as a woman pretending to be a man. Kim Yoo Jung is Moon Geun Young's child actress too, and her 2021 Lovers of the Red Sky show is a reunion of her and this drama's director (both shows have a female painter as a lead).
Drama is very unique, at first glimpse it might look like a simple age gap romance. But the truth is the female lead here has 3 love interests (an older man, a foster brother her age, and a female gisaeng/entertainer). Two of these relationships are two-sided and not one-sided.

I am recommending Painter of the Wind here because most people might know Moon Geun Young from Catch the Ghost (due to Kim Seon Ho recent popularity).

Both female lead roles disguises herself as a man in a historical period.