Season 1

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Overview
Inspired by the documentary Wordplay, Ryan and Brian decided to attend the American Crossword Puzzle Tournament in 2008, despite never having been particularly interested in crosswords. They finished the bottom 20% of the standings at that tournament.

In response to that poor showing, they set out to improve their skills at solving (and speed solving) crossword puzzles. A week after the tournament, they began to write a blog called Ryan and Brian Do Crosswords (now defunct). Shortly after that, they recording the first episode of the then-untitled Fill Me In.

Season 1 concluded with Ryan and Brian visiting the 2009 ACPT, at which Brian claimed first place in the tournament's E Division.

Highlights

 * Includes 45 episodes which started on March 31, 208, and ended March 17, 2009.
 * Origin of the catchphrase "Have we started?" (Episode 1)
 * Composition of the Viewer Mail song
 * "Fill Me In" is named by Amanda Yesnowitz (Episode 16)
 * Birth of Lollapuzzoola puzzle tournament
 * Interviews with Jim Horne, Patrick Blindauer, Dan Feyer, Andrea Carla Michaels, Vic Flemming, Dave Macleod and Barbara Olsen, Ben Tausig, Barry C. Silk and Doug Peterson, Matt Jones, Tyler Hinman, Will Shortz, Merl Reagle, and ACPT 2009 participants
 * First iteration of what would become the Thunder Round (Episode 20)