Two things are guaranteed to grab my attention in a Riddler Column - Dungeons and Dragons (DnD) and probability spaces small enough to enumerate all combinations.

Sometimes I see a Riddler Classic that makes me just want to go attack it with Monte Carlo analysis.

Today’s Riddler has a problem - you have a music player with 100 songs, and can only seek a song with “next” and “random”. “random” chooses a number uniformly in 1:100, next is track + 1, and 100 wraps back around to 1. You’ve started on a random track, and want to get to track 42, with as few presses as possible.