Since I'm in a listing mood...

Coolest philosopher in history: Socrates

Coolest King in history: Peter the Great

Coolest Queen in history: Catherine the Great

Coolest guy to become president in history: Ulysses S. Grant

Coolest presidency: FDR

Coolest General in history: hmm...this one's tough...it's either Rommel, Patton, Hannibal, Yamamoto, George Washington, Nuno Alves Pereira, or if you count him as a general, Spartacus.

Coolest Communist: Ho Chi Minh...take that Che.

Most Overrated General: Robert E. Lee edges out Napoleon.

Most Evil Person in History: Hitler

Most Evil Person in History not in the 20th century: Ivan the Terrible

(Most Evil Rulers of all time:
1. Hitler
2. Stalin
3. Mao
4. Pol Pot
5. Ivan the Terrible
6. Nero
7. King Leopold II
8. Ne Win
9. Robespierre
10. Ying Zheng) [5 in the 20th century]

Worst President: Harding if he lived long enough...but really it's Buchanan. George W. is making a run for it though.

Worst Vice President: Aaron Burr

Best Vice President: tough because he doesn't do anything...I'll give it to Nixon.

Worst Secretary of State: Dean Acheson (I blame him for the Cold War)

Best Secretary of State: William Seward

Worst Secretary of Commerce: Robert Lamont

Best Secretary of Commerce: Herbert Hoover

Worst Secretary of Defense/War: : Simon Cameron (yes, worse than the scapegoat Rumsfeld)

Best Secretary of Defense/War: tie between Stanton and Stimson

Most Overrated Political Theorist in History: tie between Machiavelli and Locke

Most Underrated Political Theorist in History: tie between Clausewitz, Hobbes, and Sun Tzu