Vicious conquerors dinner:

Attila the Hun
Tamerlane
Blackbeard the Pirate
Eric the Red
Richard the Lionheart

(supply appropriate cutlery, and watch the action!)

Nasty little men dinner:

Woody Allen
Gerry Lewis
Rowan Atkinson (Mr Bean)
Peter Lorre
Groucho Marx

Thorns in America's side dinner:

Ho Chi Minh
Fidel Castro
Muammar Ghaddafi
Saddam Hussein
Mao Tse Tung

Also-rans dinner:

George McGovern
Barry Goldwater
Michael Dukakis
Hubert Humphrey
Harry Lee Wigley

Women you've never thought of dating dinner:

Twiggy
Golda Meir
Margaret Thatcher
Tammy Faye Bakker
Joan Rivers

- LH