appeared on an episode of @midnight aired May 15, 2017, during the fourth season, which he won. As a result, he served as the funniest person on the internet for May 16, 2017. An announcement in April 2019 named Jennings as one of eight recurring "Trivia Experts" for the new Game Show Network program Best Ever Trivia Show, hosted by Sherri Shepherd. The show premiered at 4:00 p.m. ET on June 10, 2019. He was also one of the six trivia experts on Best Ever successor, Master Minds, which premiered at 4:00 p.m. ET on April 6, 2020, with Brooke Burns as the host. In November 2020, it was announced that Jennings would be one of the 3 chasers on the ABC revival of The Chase, hosted by Sara Haines with Rutter and Holzhauer as the other chasers, joined by Mark Labbett in season 2. Jennings left after the second season. American Crossword Puzzle Tournament Jennings won the rookie division of the American Crossword Puzzle Tournament in 2006. In his first time competing, Jennings placed 37th overall. He also served as the award's presenter, becoming the first contestant to present an award to himself. He has not competed in the tournament since. Kennections Jennings had a weekly trivia column, Kennections, in Parade magazine. In it, five questions were posed whose answers were connected to a mystery topic, which the readers had to guess. Parade ceased the quiz in early 2015, and removed links to archived quizzes in March 2015. Kennections now appears in the online version of Mental Floss magazine. Tuesday trivia emails Every Tuesday, beginning July 4, 2006, Jennings sent out an email containing seven questions. The seventh, a question asking what several items have in common, was designed to be Google-resistant. Subscribers responded with the answers to all seven questions and the results are maintained on a scoreboard on Jennings' blog. Every ten weeks, the respondent with the most seventh questions correct was awarded a signed copy of his newest book. After 800 quizzes, as of November 16, 2021, due to an ever-increasing amount of commitments related to Jeopardy!, book tours, and simply starting to run out of material for the seventh question, Jennings decided to discontinue this email. Controversial tweets Jennings is an active Twitter user, and some of his tweets have been subjects of controversy. On September 22, 2014, he received criticism after tweeting, "Nothing sadder