Cites:
1.) Glasgow
2.) Chicago
3.) Sydney
4.) Krakow
5.) St.Petersburg
6.) Durban
7.) Kyoto (Way too crowded)
8.) Ramallah (I don't wanna go boom)
9.) Ouagadougou (I don't want exotic jungle diseases)
Leaders:
1.) Ron Paul
2.) Marine Le Pen
3.) Angela Merkel
4.) Boris Johnson
5.) Maggie De Block
6.) Fredrikson/Tan/Mugabe
7.) Vladimir Zhirinovsky
Historical:
1.) Jesus
2.) Gandhi
3.) Madeleine McCann
4.) Thomas Jefferson
5.) William Wallace
6.) Frederick the Great
7.) Napoleon Bonaparte
8.) Sir Salty (Just kidding, I'd probably put him at 4)
9.) Karl Marx

Cities:
Sydney, Australia (Melbourne's better imo)
Kraków, Poland
Kyoto, Japan
St. Petersburg, Russia
Glasgow, Scotland
Chicago, US
Durban, South Africa
Ramallah, Palestine
Ouagadougou, Burkina Faso

Politicians:
Angela Merkel
Boris Johnson
----
Maggie de Block, Marine le Pen, Mette Frederiksen, Ron Paul, Tony Tan, Vladimir Zhirinovsky (never heard of them, unranked)
----
Robert Mugabe (last)

People:
Gandhi
Frederick The Great
Jesus
Napoleon Bonaparte
Madeleine McCann
Thomas Jefferson
Karl Marx
William Wallace
SirSalty