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OLIVIA has many dark and melancholic songs. I love the B-side of Sailing free called Love, Love, Love. a little pain, Collecting Sparkles, Starless Night, Dreamcatcher, Shadow Of Love, Winter Sleep.
She is one of my favourite artists. I made a post with her discography I don't know if the links are still up but go check (see my signature). You should check all her songs, specially after 2001.
A movie character from All About Lily Chou Chou called Lily Chou Chou (sang by Salyu) has many dark-melancholy songs.
Chihiro Onitsuka has tons: Borderline, Innocence, Bokura Barairo no Hibi, Watashi to Waltz, Rasen, etc.
BONNIE PINK also has some melancholy songs: Cotton Candy, Water Me, Last Kiss, Ocean, Bedtime Story.
Now I'm addicted to NIKIIE. On her last album, Equal, she has one song that I love and it's melancholic. It's mannequin.
Another song that I love specially the piano is from HY, called 366-nichi.
Chara also has some: kiss, Swallowtail Butterfly ~Ai no Uta~, Niji wo Wataru Heiwa ga Kita, etc.
I am addicted to a new indie duo called Haruka to Miyuki. They have a song I found on Youtube called Vanilla. I really like it.
moumoon also has some melancholic-type songs: Doko e mo Ikanai yo, Aoi Tsuki to Ambivalence na Ai, Blue Rain, Destiny, etc.
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