I have watched this drama when I was younger back in 2009. Though not understanding everything in the story, I was able to see that it was a great drama. Through the years, I often find myself watching clips from the drama (especially with that beautiful soundtrack) and reading up on it to understand more on the story. 2021, I decided a rewatch is needed for me to see if this drama holds up and for me to completely understand the story while watching as a grown up.
The drama really does hold up. but first, I completely understand why not a lot of people might like this drama. If you're someone who watches dramas for handsome "oppas", this drama is not for you. There are no oppas here, closest we get is the son of one of the villains (he's not exactly the best character either) or if you count Moon Geun Young's handsome manly disguise then that could be your oppa. Second, if you watch historical dramas for action and swordfighting, this is not your show. This drama focuses more on painting and we have a lot of gayageum (Korean instrument) music too but not a lot of swordfighting. There is a female assasin often feautured when there are action scenes, but there's not really a lot of them in this drama (female assassin is a minor character). Also the drama can be confusing to some if the historical context is not known. I suggest people read up on Crown Prince Sado (to understand the dilemma of the King in this drama) or even King Sukjong (a previous King who had issues with Queens and concubines, he eventually made a law that no concubine can be Queen, this helps viewers understand why the King's stepgrandmother is so young).
Now here are the reasons why this drama does hold up. I don't know about the others but I think the plot is really tightly written. The storytelling is consistent, we really get through the dilemmas and experiences of young artist Shin Yun Bok (a woman who has to disguise herself as a man to become an artist in a world that doesn't accept women to be among those). I especially like how well a story they made that somehow involves the real life paintings of the real life painters the two main characters are based on. The many paintings of this drama really helped me get to know more about Korean paintings and artworks. (I prefer Shin Yun Bok's paintings a lot more than Kim Hong Do's due to the vivid colors and depiction of beautiful women).
The unique relationships! Oh the relationships in this drama! Main character Shin Yun Bok has three potential love interests. None of them typical and all can be considered taboo. First is Shin Young Bok (her foster brother) whose potential romantic interest in her is seen as taboo since society sees them as siblings (plus people think she's a man). Yun Bok doesn't really love him romatically the way he does, but she truly values him as a sibling and is really appreciative of everything he sacrificed for her. Second is Jeong Hyang whose relationship with her is taboo since she's a gisaeng (belonging to someone else) plus knowing the truth that Yun Bok is a woman, they can't be together in historical times. Their love is mutually romantic, most people watching this drama are drawn to this relationship the most since it's about two young women who are both similar yet different yet somehow found love and solace on one another. Third is her teacher Kim Hong Do whose eventual romantic relationship with her is taboo since the world sees her as a man, and even as a woman they are really taboo since he's her teacher and he's very much older than her (plus he knew her since she was a child). Unlike some people who watch this drama, I think Yun Bok very much loves her teacher romantically as she loves Jeong Hyang romantically. She loves Jeong Hyang as a woman who can relate to another woman, she loves Hong Do as a woman who wants to be loved by a man. Thus for the uniquely beautiful relationship this drama portrays plus my love for the storytelling as mentioned in the previous paragraph I am giving this drama's storytelling a solid 10.
For acting, I am giving a 9.5. Moon Geun Young's acting in this drama is so fantastic, she completely sold me on her acting as a woman disguising to be a man, no other actress comes close. She truly deserves her daesang and her baeksang award from this drama. Plus the way she emotes, she's so good! It is this drama that made her one of my most favorite actresses (even if I haven't seen most of her other works except My Little Bride and some clips of Autumn in my Heart, and Love Me Not movie). Park Shin Yang is also really great but I feel like the way he speaks does not fit historical dramas sometimes, he's still great in this show. Two other fantastic actors here are Ryu Seung Ryong and Bae Soo Bin, the former being so good and scary as one of the villains Kim Jo Nyun the latter being so good and charismatic as King Jeong Jo (I was really amazed with Bae Soo Bin here, my image of him before this drama was the very feminine Sayong of Jumong). Moon Chae Won as the gisaeng Jeong Hyang is so beautiful, she also acts really good and cries prettily (there are some imperfections on her acting but given that she's a rookie here, i'm gonna forgive her). Plus she really has fantastic chemistry with Moon Geun Young (they really deserve their best couple award), her talent of having really great romantic chemistry with her partners which we can already see in this drama has brought her success on her later dramas as a lead actress (ex: Princess's Man, Innocent Man, Flower of Evil). Thus my 9.5 rating for the acting in this drama.
The music in this drama is superb. Both "Still thinking of You" and "Two Lovers under the Moonlight" are two of my favorite soundtracks from Korean dramas ever, they are so good. I also really love the songs "Flower Tears" and especially "Line of Sight", the lyrics really depict the feelings of the characters of the drama. A perfect 10.
Rewatch value is only 7.5. While the whole drama is really great, some scenes (especially scenes of older men plotting might be boring to some viewers). The great parts are really rewatchable though. My favorites are Yunbok/Jeonghyang scenes, Yunbok dressing up as woman scenes, Hongdo whenever he almost finds out Yunbok as a woman, plus episode 10 where the part where Hong Do uses Yunbok's bra (which he was confused what it was for) to clean himself is so funny.
All in all I give this drama a 9.5. Kudos to the whole cast plus director Jang Tae Yoo. I'm very much excited for Hong Chun Gi, another painting drama by this director coming later 2021 starring Kim Yoo Jung (child Shin Yun Bok here).