I can’t help myself, I love musicals. Try out the 1972 adaptation of the 1968 musical, Man of La Mancha. It has a really lovely cast album, too. But on a less La Mancha centric note, I think you rather might enjoy Guillermo del Toro’s Pan’s Labyrinth (2006). It is a gorgeous and mythic yarn spun in a more blatantly dark (though I would argue equally so when you consider Don Quixote’s sad state and the destruction that follows him. And also, it’s spanish. But more importantly, it revolves around a girl, Ofelia, who becomes lost and deeply buried in her dreams and imaginations (or her reality) and tries to escape the Francoist Spanish Civil War terror that besets her pregnant mother and herself. It is one of my favorite films of all time, and I am fine with making a bit of a stretch in order to recommend it, but I think it fits very well thematically.
I am rather a fan of the TV Movie Don Quixote from the year 2000. It stars John Lithgow as the titular role and he is simply delightful to watch and walks the line of funny and concerningly delusional with aplomb. I will throw in, if you’re looking for a different look at what it takes to make a movie like this, try looking a bit at the unfinished Orson Welles’ Don Quixote (1992) , which features perhaps the most tragic titular lead…the filmmaker. Welles had a great deal of trouble producing his melancholy adaptation, and it was posthumously edited and released incompletely, which really underlines the frustration and high flying dreams that fall to ground of both Quixote and Welles. Good stuff, good stuff.
Don Quixote is a very original book and it is hard to get anything the exactly matches the style of the story. But this is also a hugely influential work of literature and I can provide suggestions for stories that drew from Cervantes’ work. One dark and interesting example is the novel Madame Bovary by Gustave Flaubert. Another french novel, yes I know I recommend a lot of French works, this story focuses on a woman living in provincial France struggling for purpose. It is a dark story but the journey of Madame Bovary is interesting and engaging if you enjoyed the struggle of Don Quixote.
I am also a fan of the art of Salvador Dali. He was greatly inspired by Don Quixote and did a series of paintings and even a sculpture of Don Quixote himself. He also created illustrations of scenes from the novel. These works of art are a beautiful interpretation of the story and worth looking into if you are interested in an artist’s take on this famous book. Dali’s surrealist style influences these works of art and captures the struggle and unrealistic nature of this epic tale. Dali’s works are easily available to view online but I would also recommend a visit to a museum to see them in person if possible.