My own choices:
Top 5 most over the top characters:
Federation Era
1. Papa Shango
2. Nailz
3. Akeem
4. Honkytonk Man
5. Max Moon
New Generation Era
1. Mantaur
2. Bastion Booger
3. Jean Pierre LaFitte
4. Body Donna Skip
5. Goldust
Attitude Era
1. Rikishi
2. Val Venis
3. Artist Formerly Known as Goldust
4. Gangrel
5. Dude Love
Ruthless Aggression Era
1. Mordechai
2. Boogeyman
3. Hirohito
4. Hornswoggle
5. Deuce & Domino
PG Era
1. El Torito
2. Los Matadores
3. Fandango
4. StarDust
5. The Bunny
Top 5 most over the top characters:
Federation Era
1. Papa Shango
2. Nailz
3. Akeem
4. Honkytonk Man
5. Max Moon
New Generation Era
1. Mantaur
2. Bastion Booger
3. Jean Pierre LaFitte
4. Body Donna Skip
5. Goldust
Attitude Era
1. Rikishi
2. Val Venis
3. Artist Formerly Known as Goldust
4. Gangrel
5. Dude Love
Ruthless Aggression Era
1. Mordechai
2. Boogeyman
3. Hirohito
4. Hornswoggle
5. Deuce & Domino
PG Era
1. El Torito
2. Los Matadores
3. Fandango
4. StarDust
5. The Bunny