Jennings appeared on the Late Show with David Letterman to present Letterman's "Top Ten List" ("Top Ten Ways to Irritate Alex Trebek"). He appeared again on the program on the night his final show was televised, in addition to interview segments airing that night on local late evening news programming and on Nightline. Barbara Walters selected Jennings as one of the "Ten Most Fascinating People of 2004" for her twelfth annual ABC News special, which aired on December 8, 2004. While on his media tour following his final game, Jennings taped a segment for Sesame Street. TV Guide featured a segment of "The Top Ten TV Moments of 2004", in which Jennings' loss placed third. On December 1, 2004, A&E aired an episode of Biography on Jennings and other Jeopardy! notables, including Frank Spangenberg and Eddie Timanus. Jeopardy! tournaments On December 28, 2004, Sony announced a 15-week, 75-show Jeopardy! Ultimate Tournament of Champions. It featured Tournament of Champions, College Championship, and Teen Tournament winners from the show's 21-year run, as well as over 100 five-time champions. Jeopardy! executive producer, Harry Friedman, explained, "The 2003 rule change, which allows Jeopardy! players to keep playing until they're defeated, raised the question about how other five-time champions might have played under this rule. This tournament is an opportunity to give those past champions another chance to shine." The field totaled 145 players including Jennings, who, unlike the other competitors, was automatically placed in the finals. The Ultimate Tournament of Champions offered substantial cash prizes; with a grand prize of $2 million to the winner, $500,000 for the first runner-up, and $250,000 for the second runner-up. Guaranteed prize money was offered to all contestants. In the final round of the Ultimate Tournament, Brad Rutter decisively defeated Jennings and Jerome Vered, with respective final scores of $62,000, $34,599, and $20,600. Jennings won the $500,000 prize for second place, but as a result of the Ultimate Tournament, Rutter temporarily displaced him as the highest overall winner of money on game shows. Jennings has said he is still happy with his second-place finish. From February 14–16, 2011, Jeopardys "IBM Challenge" featured the company's Watson against Jennings and Rutter in two matches played over three days. The winner of the competition was Watson, winning $1 million for two charities, while Jennings was second and Rutter was third, receiving $300,000 and $200,000, respectively. Jennings and Rutter each pledged to