August 4, 2007, and featured 16 former game-show winners in a single-elimination tournament. Jennings, seeded second behind Brad Rutter, won the tournament and became the 2007 Grand Slam Champion after defeating Ogi Ogas (a second-round winner against Rutter) in the finals. He earned $100,000 for his victory. Jennings was a contestant on an episode of Are You Smarter Than a 5th Grader? that aired on October 10, 2008, which held the possibility of exceeding Rutter's total game show winnings. After winning $500,000, enough to surpass Rutter's total, Jennings chose not to attempt the final $1-million question, which would have deducted $475,000 from his winnings if he missed it. As is customary on the show, Jennings was then shown the question to see what would have happened, and he provided the correct answer. Had he risked his winnings and correctly answered the question, he would have become the show's second $1-million winner. From 2008 to 2009, Jennings appeared on GSN on Fridays for the trivia game Stump the Master, where home viewers submitted questions via the GSN website. Four callers were put on hold and Jennings selected from one of the categories. The caller for the category he picked came on the line and read the question. If Jennings didn't answer or was incorrect, the caller won $1,000 or more. When Jennings was right, the jackpot was increased by $1,000. All callers were given a small prize whether they participated on-air or not. Jennings has appeared on multiple episodes of Doug Loves Movies, hosted by Doug Benson, and has won a few times. Jennings also appeared on two other Sony Pictures Television game shows, Who Wants to Be a Millionaire, as a frequent expert for the lifeline "Ask the Expert", and also taped a pilot for the proposed 2009 CBS revival of Pyramid, titled Million Dollar Pyramid. Jennings appeared on Millionaire in 2014 as a contestant during Guinness World Records Edition themed week, where he won $100,000 after deciding to walk away on his $250,000 question. If he had gone for it, he would have been right and would have won $250,000. Jennings appeared on the second-season premiere of 500 Questions on May 26, 2016 and was eliminated on the fourth question by winter 2012 college champion Monica Thieu, leaving with no winnings. Jennings later teamed up with Thieu, along with Matt Jackson, in the Jeopardy! All-Star Games in 2019. Jennings