I think this is worth discussing.
2003 Winners
*This doesn't include the awards for topics*
Drama Queen
XVII
Best Moderator
Newgrundling
Worst Grammar
allpro
Biggest Spammer
wolf-
Worst Poster
-78-, 5and3r, & allpro
Mr. Coherent
Dobio
Most Underappreciated User
-78-
Pro Flamer
Dobio
Funniest Poster
HeniousDude
Mr. or Miss. Nice Guy/Girl
Captain-Jack (then known as Nephthys)
Best Poster
Shrapnel
2004 Winners
Most Innovative User
poxpower
Funniest User
bigbadron
Attention Whore
GoldenCat (not sure what username he's going by now)
Drama Queen
Shin2k27
Never Logs Off
ZeroAsALimit
Mr. Coherent
liljim
I Miss Yew
Livecorpse
Most Overrated User
IllWillPress
Most Underrated User
maus
Biggest Spammer
GoldenCat
Best Moderator
Joe (Then known as TheJoe234)
Worst Moderator
Ozcar
Worst BBS Poster
WeedClock
Best Poster
OsAmARaMa
2005 Winners
Funniest User
poxpower (then with "-'s")
Attention Whore
fukmehardNpullmyhair
Drama Queen
-Dawkins- (Deleted)
Never Logs Off
Maus
I Miss Yew
bigbadron & DanMalo
Most Overrated User
Josh (then known as DEATHKNELL)
Underrated User
GreenLantern
Biggest Spammer
BonusStage
Worst Poster
fukmehardNpullmyhair
Best Mod
Maus & Newgrundling
Worst Mod
Sarai
Best Noob
protege-moi
Best Topic Starter
Earfetish
Best User (Male)
BadReligionSkater (BRS)
Best User (Female)
Maus
2006 Winners
Funniest User
wwwyzzerdd
Biggest Attention Whore
HotActionYiffFur
Drama Queen
WadeFulp
Never Logs Off
ZeroAsALimit
I Miss You
Denvish
Best BBS Story Writer
Earfetish
Best Artist
Stamper
Biggest Spammer
HotActionYiffFur
Best Creator Of Topics
dave
Rookie Of The Year
Paradox
Most Overrated
HotActionYiffFur
Most Underrated
RedCoin & Gendo
Worst Moderator
JoS
Best Moderator
Maus
Worst BBS Poster
Zen444
Best BBS Poster
wwwyzzerdd
2007 Winners
Funniest User
AshfordPride
Biggest Attention Whore
Mechabloby and Zen444
Drama Queen
cellardoor6
Never Logs Off
ZeroAsALimit
I Miss You
Denvish
Best Artist
ZekeySpaceyLizard
Master Creator
AshfordPride & BlueFlameSkulls
Rookie of the Year
Mendou
Most Improved
HotActionYiffFur
Biggest Spammer
BigFuzzyKitten
Most Overrated
WilliWowza
Most Underrated
Luxury Yacht
Worst Mod
RedDakota
Best Mod
Zerok
Worst Poster
mariobro42
Best Poster
BlueHippo
Maus and HotActionYiffFur are tied for the most awards (4 each). HAYF holds the record for most awards in 1 year (3). Other multiple award winners are:
ZeroAsALimit - 3
-78- - 2
allpro - 2
AshfordPride - 2
bigbadron - 2
Denvish - 2
Dobio - 2
EarFetish - 2
fukmehardNpullmyhair - 2
GoldenCat - 2
Newgrundling - 2
poxpower - 2
WadeFulp - 2 (1 as WadeFulp, 1 as RedDakota)
wwwyzzerdd - 2
Zen444 - 2
All users to win Best User Awards have been mods or became mods with the exception of myself (2006 winner).
Denvish has won the I Miss You Award 2 times.
Other than Best/Worst Mod awards, Newgrounds staff members have won 20 awards (if you count the 2006 I Miss You award tie as 2).
JoS is the only mod to win a Worst Mod Award and still be a mod.