Well, if they made a cartoon based on the old CLUE book series.

1)Gerald Green; greedy corrupt businessman, really hates Mrs. Peacock.
a)Bubs.
b)Strong Bad.

2)Precilla Peacock; Manners prude, pre-internet troll, hypocrite, hates Mr. Green.
a)Marzipan.

3)Paul Plum; Well-meaning idiot who can't remember his own name & funds projects with loot from stolen merchandise, doesn't get along with White.
a)Homestar.
b)Homsar.
c)Coach Z.
d)Senor Cardgage.

4)Wilhelmina White; Lazy antisocial, greedy, ungreatful, violent maid/cook to Body, detests Plum.
a)The Cheat.
b)Strong Mad.
c)Strong Bad.

5)Martin Mustard; Thinks he's still in the military, barks orders, chivalrous, loves guns & duals, doesn't get along with Scarlet.
a)Bubs.
b)The Cheat.
c)Pom Pom.

6)Charlotte Scarlet; Vapid, shallow, fake emotions, uses men for their money, vain, clashes with Mustard.
a)Strong Bad.
b)The cheat.
c)Coach Z.

7)Reginald Body; Poor taste in friends, overly forgiving, loves to show off his latest purchases, overtly optimistic, as lucky as unlucky.
a)King of Town.
b)Strong Sad.

The Princess Bride:

Marzipan: BUTTERCUP
Homestar Runner: WESTLEY
Coach Z: PRINCE HUMPERDINCK
Strong Bad: INIGO MONTOYA
Strong Mad: FEZZIK
Strong Sad: VIZZINI
Bubs: COUNT TYRONE RUGEN
Homsar: MIRACLE MAX

HSR cast as emoticons! :
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Aww thanks!

The Big Bang Theory

Leonard: Homestar
Sheldon: Strong Sad
Howard: Coach Z
Raj: The Poopsmith
Penny: ...I suppose Marzipan's the only choice, but it doesn't really work...
Howard's mother: So-and-So's stepmom

LOL, that's good!
I think should also have though.
But it's still a pretty cool idea!

Aw, I'm DYING to do The Office... Too bad none of their personalities really fit... Psh. I'll try anyway.

- Michael (They're both well-meaning and stupid. And the main character.)
- Toby (This just... works.)
- Jim. (The closest thing to a Jim. Unfortunately, nobody's a Pam.)
- Ryan (The new, mean, trying-to-be-cool Ryan at least.)
- Kevin (YES.)
- Angela (They're both blonde vegetarians.)
- Stanley (Just cuz. I can picture him saying some of Stanley's lines. 'DID I STUTTER?")
- Creed (YES YES YES.)

Awww... sucks I couldn't think of a Dwight or an Andy... but nobody can quite fill Dwight's amazingly quirky shoes... Any suggestions?

BubbleRevolution is all wrong your idea of the simpsons

- Homer Simpson
- Marge Simpson
- Bart Simpson
- Lisa Simpson
with a pacirfer - Maggie Simpson
- Santa's Little Helper
Mr. Pitters- Abe Simpson
- Milhouse van Houten
- Apu Nahasapeemapetilon
- Mr. Burns
- Waylon Smithers
Tompkins- Nelson Muntz
- Ralph Wiggum
- Moe Szyslak
Señor - Uter
Mr Bland - Barney Gumble
The Umpire - Skinner
- Jeff Alberteson
Nebulon - Kang
Rumble Red -Kodos

A lot of the good ones have already been taken, but let's see if I can't whip something up:
Ned's Declassified School Survival Guide (first thing that came to mind):
Ned Bigby (naturally)
Simon 'Cookie' Nelson Cook (Maybe you'd expect him to be Loomer, but he's not big enough, first of all, he's not dumb enough, second, and third, he's the only one nerdy enough to pull off Cookie. Plus I can't get over making him Homestar's right hand man w00t.)
Jennifer 'Moze' Mosely (Okay, this took me FOREVER. Thing is, I wanted Marzipan to be Suzy, so I couldn't use her here. Thus, I was desperate. I just thought of Coach Z because he's the only other athletic one, and the only one with a close enough body build. I know, totally Jibbly worthy. God, this is horrible.)
Suzy Crabgrass (I'm not sure why. I think just because she's not cool enough to play Jennifer.)
Billy Loomer (for obvious reasons. If they're not that obvious to you, see Strong Bad's explanation.)
Gordon 'Gordy' B. Rockefeller (Dang it! Now I can't use Coach Z for Gordy! Dangcrapple! Ah well. Good thing they have another janitor type person.)
Seth Powers (Mmm.....alright.)
Well, I wanted him to be Ted, the black teacher/principal dude, but I can't remember his last name. So I guess....Mr. Monroe? Maybe?
Coconut Head (who else?)
Missy Meany (LOL. I love doing this.)
Evelyn Kwong (I really don't know why.)
Vice Principal Crubbs (Strong Bad would probably be better for this role, but don't you think that maybe he's suffered enough?) Oooh, wait, better yet:
Principal Pal (Total ownage.)
Coach Dirga (maybe)
Okay, I'm getting bored with this. If anybody wants to add anything, go right ahead.

^ I love that song!