I consider myself a casual anime fan. I enjoy the obvious mainstream ones like Dragon Ball(Z)(GT), Full Metal Alchemist, Pokemon and Cowboy Bebop, but I don't venture out of really popular anime like those.
 
My favorite anime is probably Great Teacher Onizuka, though. It's a comedy anime with a high school setting. Does anyone have any anime that are similar to that, a very funny anime with a realistic setting? 
 
Also:  

• Don't say Naruto.
• Anything with naked cartoon pussy is welcome.
• For the love of God, don't say "Anime is for jerks."

Have you seen Samurai Champloo? One of my favorites.

So blah blah standard list of shit that was on Toonami and Adult Swim over the years. 
As for what you're looking for, I'd say most harem anime is attempting to be funny and takes place at during high school. School Days is a happy funtime anime, try that.

" I was going to say Cowboy Bebop . . . I guess that shows you how much anime I watch. "

supposedly Shuffle has boobs so i suppose that's kind of like Naked Cartoon Pussy. Hayate the Combat Butler is very, very funny from JJOR's review so i'd check that out. 

If you was talking about manga I could help you out

What kind do you want?
 
 
EDIT: Sorry skimmed through your post. 
 
 
You'd like School Rumble definitely it sounds like what you're looking for.

if you want to find good anime suggestions you could probably go to anime vice and find something

Monster

FLCL.

Serial Experiments Lain and Witch hunter robin

We had a really extensive thread on the subject.  You could just search or something...
 
One I was referring to.

Soul Eater

" We had a really extensive thread on the subject.  You could just search or something...
 
One I was referring to. "

I think I'm in about the same boat as you, I like anime but don't stray too far from the mainstream. 
 
Anyway one show I would recommend that hasn't been said yet would be Elfen Lied.  It's a very short series (13 episodes), I enjoyed the story. There is plenty of blood and cartoon boobies. 
 
Also, of all the anime I have watched it has the best opening sequence and theme song by far. No J-Pop.

If you like boobs, Dragonaut: The Resonance. If you like mechs, Gurren Lagaan both are on hulu.

I liked the 2nd intro to Death Note. A lot. It fit the show perfectly. I know a lot of weabos hated it but they're the last people on earth I look to for an appraisal on good music.

I wrote a longer post with descriptions of the shows but then my laptop designed to run out of power at that second.

Bleach: The first 3 seasons are amazing, its gone some great action and interesting characters.

Mobile Suit Gundam: Great mech combat and a young kid trying to survive in war. Theres a lot in this franchise and it seems to expect you to know what came before so its quite hard to start so I got the original films (a cut down version of the original series) and its great.

Super Dimension Fortress Macross/Robotech: Some great combat featuring transforming planes (into Robots), interesting characters and a love triangle.

Ninja Scroll: A great film with sweet violence (and a funny little old man).

Afro Samurai: NinjaNinja is really funny, some great situations and action.

Chobits: A series about a guy who finds a persocom (Personal Computer that looks like a realistic android), its mainly a love series with some interesting characters and questions.

Avatar - The Last Airbender/The Legend of Aang: Technically not an anime since its was made in America (animated in Korea I think) but it has the same heart. Its got some great action, funny characters and it poses some interesting questions (although sadly as a kids show on Nickelodeon it answers them a bit too quickly).

Legend of the Galactic Heroes: A really thick and slow anime about two warring (space) nations engaging in long drawn out battles and long drawn out planning stages.

Ghost in the shell: 2nd gig, or simply the second season.

Naruto.
 
But seriously, Durarara is a great new anime...if you can keep up with the complicated storyline. High School Of The Dead sounds hella promising. Whether it's bad or good it looks like great entertainment. If it's good then it's good. If not, you'll have a blast making fun of it with friends. However, it hasn't come out yet.

I'm obviously not the guy to come to (despite playing a shitload of JRPGs constantly), but I'd recommend Avatar. Why? Just for the hell of it. Also just for the hell of it: animes based directly off video games (Fire Emblem, Panzer Dragoon, Final Fantasy), purely for the laugh factor.

Bacanno
Durarara
Gurren Lagann

Gintama is pretty good. I think it just ended though. And you might not get a lot of the jokes.  I got plenty of chuckles out of it. Kind of like back when Family guy was new. Except it stayed that way throughout the whole 4 seasons.
 
Then there's Fist of The North Star. I would suggest watching the movie which sums up the Shin Saga from the original series. And from there I would watch "Shin Hokuto no Ken" which came out in the mid 2000's. It's a 3 parter and is incredibly awesome and brutal.  There's a shit tonne of other Fist of the north star stuff, but those two things are the best, and the rest is kind of confusing and stupid. 
 
If you liked Persona 3, there is an anime that is loosely related to it. I haven't gotten to watching more than the first half of episode 1 yet.
 
Dragon Ball, DBZ, and DBGT and then the movies are all a good way to spend 8 months of your free time. And they're gonna start releasing them all again with redone voice work.
 
The Street Fighter 2 movie is always a good choice. Avoid the Alpha movies and the Street fighter 4 movie, as they are garbage. 
 
The Hobbit of course. It's not "Anime" but it's the best movie ever made, so it's on this list.
 
Record of Lodoss War is pretty good. It's similar to many of the japanese RPG's being released around 93'. So it's like Lord of The Rings.
 
My neighbor Totoro's Pretty good I guess. If you're into heartwarming childrens movies.
 
If you haven't seen one of the 200 thousand reruns of Akira on TV then you should probably watch that for the blob animations. Which are impressive. 
 
I haven't seen Sword of Berserk in about 15 years, but I remember it being pretty great. You should watch that.
 
Other than Gintama, Shin Hokuto No ken and the persona anime everything is from the early 90's and late 80's. So there's obviously going to be translation and english voice acting issues, as well as lower resolutions. So keep that in mind.

" So blah blah standard list of shit that was on Toonami and Adult Swim over the years. As for what you're looking for, I'd say most harem anime is attempting to be funny and takes place at during high school. School Days is a happy funtime anime, try that. "

Comedy?  High School Setting?  Try out Azumanga Daioh.  It's goofy, over the top, and funny.  There is no on-going plot for the show since the manga was a 4-panel comic strip.

Samurai Champloo, Rurouni Kenshin/Samurai X, Trigun (I hear its good, haven't seen it), Hellsing, Death Note.  Samurai Champloo is by far my favorite.  It's extremely good.
 
Edit:  Oh, also:  I've watched the first two episodes of Jyu-Oh-Sei and it seems like it will be pretty good, and it's only 11 episodes so it's not going to be a big time investment.
 
Edit 2:  I liked Bleach up until about the 4th/5th season.  It's still alright, but the first 3 seasons I really enjoyed.  Also, I think Naruto is pretty good.  It takes about 20ish to get there, I but really like it after that.  Maybe give it a try if you have not, but whatever if you don't want to.  Also, watch it in Japanese if you do, the voice acting in english is atrocious.
 
Edit 3:  Afro Samurai.

" So blah blah standard list of shit that was on Toonami and Adult Swim over the years. As for what you're looking for, I'd say most harem anime is attempting to be funny and takes place at during high school. School Days is a happy funtime anime, try that. "

I'm a big fan of Black Lagoon, but there is only like 20-something episodes, with a third season coming. 
Bleach gets better and better as it goes on. 
Death Note is really great, but I haven't watched the second season. 
One Piece is kind of hard to start watching, because the first episodes are pretty old, so the quality is not that good, but the episodes I have watched were also really good.
 
I can't really think of anything else right now. Keep in mind that I haven't watched a lot of different animes. Also, the mangas are always better, so if you don't mind reading them on the internet, do it. Finally, I always watch them in Japanese with subs except Black Lagoon which is better in english dub (The second season starts to mix different languages and in Japanese, the characters are actually speaking english a lot of times, like they are suppose to storyline wise, but it's really poor english, anyways...)

Full metal panic fumoffu

Ghost in the Shell: Stand Alone Complex 
Death Note 
Monster

" You'd like School Rumble definitely it sounds like what you're looking for. " 

I currently rewatching Rurouni Kenshin, SDF Macross and Gurren Lagann.  I'd recommend all of those. The last one I really enjoyed were the two versions of Negima.   Negima! Magister Negi Magi is all about character development and relationships, while Negima!? Magister Negi Magi is more about action and magic.  Both are comedies, but that latter is more screwball than the former.  My favorites are The Slayers, Martian Successor Nadesico and (440+ episodes of) One Piece.   If you are looking for "naked cartoon pussy" then I suggest Ikki Tousen and Queen's Blade.  

I don't watch a whole lotta anime but I really liked Genshiken. Humorous and high school setting and mild sexual references.

For comedy I'd say Love Hina, but don't venture beyond that point with the whole harem genre.  It gets old and stale very quickly.

It's important to try things out and see what appeals to you.  Don't listen to the haters because you may find you like what someone else despises.  Who can predict personal tastes?  And, there is no good or bad taste, just different opinions.  If everyone was the same and liked the same things what a bland world this would be.  Celebrate diversity and discover what you find entertaining.

Samurai Champloo. It's on Hulu now also, so you have no excuse. Very awesome show. Amazing music also.
 
Afro Samurai is also really cool. It features Samuel L. Jackson, and has some amazing art and music. Only five episodes and a movie also, so you can finish it in a week. You won't regret it.
 
FLCL is fucking insane in every way, and you won't understand it the first time, but damn that show is unique. Personally, I'm really glad I watched it. Really strange and cool.
 
Last but not least, Avatar: The Last Airbender. I know a lot of people who haven't seen it just say it's a kids show, but it's a lot more than that. It's well written, has an interesting plot and likeable characters, and will hook you until the very end. Fantastic series.

Berserk
Claymore
 
about to start Samurai Champloo as a friend has been telling me to watch it forever now.

 Avatar: The Last Airbender. I know a lot of people who haven't seen it just say it's a kids show, but it's a lot more than that. It's well written, has an interesting plot and likeable characters, and will hook you until the very end. Fantastic series. "

Soul Eater!

Durarara!! 
Senko no Night Raid 
AngelBeats! 
 
 
This is some of the new stuff that I happen to like a lot.

funny anime with a realistic setting