Jeopardy! The Greatest of All Time Season 1 Episode 4 Episode 4 ( Air Date 2020-01-14 ) Genre Drama, Comedy, Talk category. Overview "Ken Jennings, Brad Rutter, and James Holzhauer compete in a series of matches in prime time. The first to win 3 matches receives $1 million and the title of “Jeopardy! The Greatest of All Time.” The 2 non-winners each receive $250,000.".