There's a sort of catharsis in listening to sad music, or reading sad poetry, and I'm looking for a word that describes how engaging in sad activities can actually be pleasurable.
I don't mean someone that revels in their own unhappiness or refuses to engage in activities that provide happiness, but rather when you want to watch a sad movie and have a good cry, even if you are generally happy.
The word that came to my mind was sentimental:
Having or arousing feelings of tenderness, sadness, or nostalgia, typically in an exaggerated and self-indulgent way.
‘a sentimental ballad’
‘I'm a sentimental old fool’
Oxford Living Dictionaries
The classic term might be melancholy, as it is used in this exchange between Amiens, who has been singing a sad song, and Jaques, who has been avidly listening, in As You Like It:
Jaques. More, more; I pr'ythee, more.
Amiens. It will make you melancholy, Jaques.
Jaques. I thank it ; I do love it better than laughing.
...
Amiens. My voice is rugged : I know I cannot please you.
Jaques. I do not desire you to please me; I desire you to sing.—I can suck melancholy out of a song, as a weasel can suck eggs. Come, warble, warble.
As Jaques says elsewhere in the same scene, his is "a melancholy of mine own, compounded of many simples, extracted from many objects; and, indeed, the sundry contemplation of my travels, in which my after rumination wraps me is a most humorous [that is, strongly felt] sadness." That is a pretty good description of the experience of luxuriating in the deep pathos of a heartfelt sadness.
If we are describing the sensation of enjoying something sad, that could be bittersweet:
n. something that is bittersweet; especially : pleasure accompanied by suffering or regret
adj. being at once bitter and sweet; especially : pleasant but including or marked by elements of suffering or regret ⋅ a bittersweet ballad ⋅ bittersweet memories
from m-w.com
Maudlin
https://www.merriam-webster.com/dictionary/maudlin
http://www.dictionary.com/browse/maudlin
maudlin: Affectionate or sentimental in an effusive, tearful, or foolish manner, especially because of drunkenness. [from 17th c.] quotations ▼ Extravagantly or excessively sentimental; mawkish, self-pitying. [from 17th c.] quotations ▼ (obsolete) Tearful, lachrymose. [17th-19th c.]
Maudlin has connotations beyond the questioner's "liking a good cry" (for example, it hints at drunkenness), but otherwise it's a good match. It implies sad emotionality for the sake of catharsis.
I don't think there is a single noun that refers to someone like that, but you can describe them as someone who has a "tragic sensibility".
sensibility: the ability to appreciate and respond to complex emotional or aesthetic influences; sensitivity. (from ODO)
tragedy: although the word tragedy is often used loosely to describe any sort of disaster or misfortune, it more precisely refers to a work of art that probes with high seriousness questions concerning the role of man in the universe (https://www.britannica.com/art/tragedy-literature)
Here are some articles that discuss the concept of "tragic sensibility": https://www.newcriterion.com/issues/2017/5/the-tragic-sensibility http://theaquilareport.com/tragic-worship-3/
A movie which is sad with an unhappy ending would likely appeal to a misery guts.
Although often used with the sense of killjoy, a misery guts is always complaining or in a bad mood, and seems actually to be happiest when things are not going well.
You can use the word masochist here.
Masochist : A person who derives satisfaction or pleasure from their own pain or humiliation.
Another reference :
Masochism is an eponym — a word named for a person. Leopold von Sacher-Masoch was an Austrian writer in the nineteenth century who described the gratification he got from his own pain and humiliation. For example,
If you call someone a masochist, you either mean that they take pleasure in pain, or — perhaps more commonly — that they just seem to.
These days, you're most likely to hear the word used jokingly by someone who doesn't understand another's motivations for doing something painful or difficult:
You're still building that stone wall? What are you, some kind of masochist?
OR
I can't believe that you are still watching that movie! What kind of a masochistic person are you ?!
I hope this answered your question. :)
Schadenfreude Pleasure derived by someone from another person's misfortune. [Oxford English Dictionary]
Origin: German
It is sad and painful for many of us to be reminded of how little we know or how bad our skills are or how things work. A person who can overcome that pain and sadness to hunt for the joy of learning the nature of whatever induces the sadness is a learner.
