That's the weirdest Jeopardy category I've even seen.
a category in "jeopardy" called "hats on ice"
top hat water skiing
A cute little hat is waterskiing!
lawl so random and quirky
poorly draw lawl
Jovial face.
English letters asking a question with a heart at the end.
He probably meant the modern roman alphabet, which he associates with English, because that is the the language with which he uses it.
Doodle or Die is the game of "telephone" with drawing!