Abstract: In 1821 John Jackson published “Rational amusement for winter evenings or, A collection of above 200 curious and interesting puzzles and paradoxes”. At least one of these puzzles has led to open problems in combinatorics about line arrangements, open problems which have recently become relevant to a growing body of work in commutative algebra and algebraic geometry. I will describe some of this work and its history and discuss how it relates to an important open problem in algebraic geometry, called the Bounded Negativity Conjecture. No background in algebraic geometry, commutative algebra or combinatorics will be assumed.