as the highest money-winner on American game shows, which Jennings had held since 2008. In 2019, Rutter teamed with fellow Jeopardy! champions Larissa Kelly and Dave Madden to win the Jeopardy! All-Star Games. Rutter was team captain and they split the top prize of $1,000,000. Rutter competed in the Jeopardy! The Greatest of All Time event in January 2020 against Jennings and James Holzhauer, and ended up winning $250,000 with a third-place finish. Other game show appearances He appeared on the U.S. game show 1 vs. 100 (as a member of "the Mob") on December 1, 2006, and again on December 8, 2006. He answered every question correctly and was one of only seven mob members to survive to the next show, as was Annie Duke. He would be eliminated on the December 15 episode on a question about Jewish reggae musician Matisyahu. He appeared again on February 9, 2007, and was eliminated late in a winner-takes-$250,000 "last man standing" competition, but before Ken Jennings was. Rutter was the top seed in Grand Slam, but lost in the second round to Ogi Ogas, a former Who Wants to Be a Millionaire contestant. Rutter competed in the 2010 World Quizzing Championship, where he finished 140th. He was also a contestant on the 6th episode of Million Dollar Mind Game (aired on November 27, 2011), where his team won $600,000. In May 2012, he did a pilot episode as a "Chaser" for an American version of the British game show The Chase. Fox network ordered two pilots for consideration in its lineup. The Chaser in the other pilot was Mark Labbett, one of the five Chasers on both the British and Australian versions of the show. Despite the show not being picked up by Fox, it was later aired by GSN, with Labbett (the Beast) as the only Chaser. Rutter was one of three chasers hired in 2020 for the ABC revival of The Chase, along with Jennings and Holzhauer. In May 2020, Rutter appeared on a revival of Who Wants to Be a Millionaire as an in-person lifeline for celebrity contestant Catherine O'Hara. On the show, celebrities playing for charity were allowed to have an expert assist them in answering the first 10 questions—Rutter served as O'Hara's expert and helped her answer each of the 10 questions correctly. After this point, O'Hara made the decision to trade her 50:50 lifeline for