During his first run of Jeopardy! appearances, Jennings earned the record for the highest American game show winnings. His total was surpassed by Rutter, who defeated Jennings in the finals of the Jeopardy! Ultimate Tournament of Champions, adding $2 million to Rutter's existing Jeopardy! winnings. Jennings regained the record after appearances on several other game shows, culminating with his results on an October 2008 appearance on Are You Smarter Than a 5th Grader?, though Rutter retained the record for highest Jeopardy! winnings and once again passed Jennings' total after his victory in the Jeopardy! Battle of the Decades tournament. In 2020, he once again faced off with and won against Rutter, as well as James Holzhauer, in a special primetime series, Jeopardy! The Greatest of All Time.
