I nominate the following characters:
Negi Springfield : Mahou Sensei Negima
George Bush Jr. : Mudazumo Naki Kaikaku / The Legend of Koizumi
Reiji Arisu (top and comes from Namco X Capcom) and Haken Browning (bottom) : Super Robot Taisen Original Generation: Endless Frontier
Ryugamine "Moot" Mikado : Durarara
Adolf Hitler : Mudazumo Naki Kaikaku / The Legend of Koizumi
Demon Xavier : Sengoku Rance
That should be enough for now.