Honestly, really really disappointed that Skearhead is alive. It's absolutely going to turn out that Ellelain never really betrayed the Empress and that Skearhead manipulated things to continue the war. I really liked his previous character; extremely loyal but completely misguided. It feels really cheap to cop out of the "maybe Ellelain was a flawed person who messed up" plotline.
Absolutely it has to be Shitsurakuen.
I actually really like most of the manga. It's a fun and goofy harem take on Revolutionary Girl Utena (right down to the title; Paradise Lost (Shitsurakuen) is referenced in the most famous song of the show). The character designs are cute, the art is nice, and I like all their interactions.
Unfortunately, the ending sours any enjoyment I have for the series. It is really short and I don't not reccomend reading it, but it's very much clear the author took one look at Utena's themes and then just... did not understand them, at all. I'll leave my feelings about it behind a spoiler. In short: You can't just reward your abusive baddies with the girls they like returning their feelings; that's not satisfying! You need SOME character development!
For anime, it's probably gotta be Shikimori's Not Just a Cutie. And I'll be nice and say my hate for it is born out of love for what could have been. I was really excited for the show based on the opening, and I thought all the characters were really cute, but it was super stretched out and boring as hell, and Shikimori as a "cool girl"/pseudo-yandere was really underutilized! I really liked Kamiya's episode, and basically any part with Hachimitsu, but the rest was really tiring to sit through.
Sayonara Zetsubou Sensei is the first to come to mind, though I'm not sure if that is what he's looking for...? It's a comedy, but it is, you know, about suicide.
If you want something more serious with an episodic nature, maybe MUSHI-SHI? xxxHolic (and CLAMP's works in general) also has a weird balance of comedy/slice of life style things and dark subject matter. I would also say anything directed by Kunihiko Ikuhara will tend to have a weird balance between those two tones, and I am always suggesting people check out his work.
Hope those help a little! Good luck finding something :D