| What was the most... | Year | Answer | Extra hint | % Correct |
|---|---|---|---|---|
| ...captured city in world history? | many times since the 8th century BCE | Palermo | Currently the capital of Sicily | 62%
|
| ...lopsided electoral college result in any U.S. presidential election? | (answer the year) | 1936 | FDR was elected | 54%
|
| ...disputed area of land in South Asia? | since 1947 | Kashmir | This conflict flared up again in 2025 after a terrorist attack | 38%
|
| ...destructive period of civil unrest in U.S. history, excluding the Civil War? | 1992 | LA Riots | ~1,100 buildings destroyed | 23%
|
| ...disastrous diplomatic failure in modern geopolitical history? | 1938 | Munich Agreement | "Peace in our time"? Yeah, right | 23%
|
| ...costly natural disaster in world history? | 2011 | Tōhoku earthquake and tsunami | Cost $360 billion | 23%
|
| ...lopsided popular vote result in any U.S. presidential election? | (answer the year) | 1920 | A desire for a "return to normalcy" may have played a part here | 15%
|
| ...corrupt local politician in U.S. history, by most measures? | c. 1860-1871 | William "Boss" Tweed | Ran New York's "Tammany Hall" political machine | 15%
|
| ...long-lasting battle in WWII? | 1939-1945 | Battle of the Atlantic | Lasted nearly the entire length of the war | 8%
|
| ...deadly maritime disaster during WWII? | 1945 | Wilhelm Gustloff sinking | Around 9,400 people died, many of them civilian refugees | 0%
|