Ok, first off, I'm looking for something really depressing; something that makes your heart squeeze and might even set me off crying. Don't ask me why, because I don't really know. I just want to read something like this.

Second, I'm looking for something Gut-splitting, like Skip Beat or the first 90 chapters of Gokusen (Past 90 they start just getting stupid..)

Yeah, thats pretty much it.

Oh. PLEASE DO NOT SUGGEST ANYTHING ON MY LISTS! However, don't bother looking at my on-hold list. Thats just where I put my wish-listed Hentai until I can locate them or until they're scanalated.

Does the walker choose the path, or the path the walker?

Depressing:
Deep Love - Ayu no Monogatari
Mucha Kucha Daisuki

Funny:
The Wallflower
School Rumble
My Name is Zushio but it's too over the top...
Yotsubato!
Zippy Ziggy
Yankee-kun to Megane-chan
Mx0

NHK ni Youkoso! is both funny and depressing, though more comical than heart wrenching I guess.

Hand Rooster is a rooster made with your hands.

For depressing, try Gunslinger Girl.

I don't read a lot of straight forward comedy. The funniest thing on my reading list that isn't on any of your lists would be Negative Happy Chainsaw Edge and it's not exactly a comedy.

Tree + Taco = Tree taco.

I second highly Gunslinger Girl. It's amazing and a really sad story. Or you can watch Hotaru no Haka anime (Grave of the Fireflies), nothing can make me depressed as that movie.
Other stuff:
Saikano
Kurogane you have this on yoru wish list. It's not depressing but it's definitely sad and I think it's good.
Shin Angyo Onshi same as Kurogane
Chrno Crusade

What I like in Trivial Pursuit style. Pick your category:[img]http://i379.photobucket.com/albums/oo233/Reid4891/Manga/trivia-1.jpg[/img]

depressing
it's already been said but....read Shin Angyo Onshi it's epic and depressing with a dope main lead
Nana
Ciguatera (fits in both)
Suzuka
Beck (kind of fits in both thoo)
Boku no Hatsukoi wo Kimi ni Sasagu
Cat Street
Real
Shamo

funny
Hajime no Ippo
i 2nd Zippy Ziggy
Do-Re-Mi-Fa-Sol-La-Si-Do
Nodame Cantabile
The Breaker
Worst
Koukou Debut
Kimi wa Pet
Karate Shoukoushi Kohinata Minoru
Slam Dunk
Unbalance×2
High School
Moyashimon

[img]http://img40.imageshack.us/img40/4158/1205047355313.gif[/img]

Thanks for all the suggestions! A couple of them I've dropped or am I already reading, but since they weren't on my lists, I can't say anything.

Does the walker choose the path, or the path the walker?