Jennings has a history of tweeting out cruel jokes, particularly at the disabled. Yvette Nicole Brown was among those on Twitter who brought up Jennings' past tweets following Jeopardy!'s announcement Monday he would be the first of several interim hosts. In 2014, Jennings tweeted "Nothing sadder than a hot person in a wheelchair." In 2015, in response to a Star Wars fan getting to see The Force Awakens before its release before his death from cancer, Jennings tweeted: "It can’t be a good sign that every fan who has seen the new Star Wars movie died shortly thereafter." In 2018, Jennings expressed regret for the 2014 tweet, writing: "I never did a public flogging thing for this but I did apologize personally to angry/hurt people who reached out personally. it was a joke so inept that it meant something very different in my head & I regret the ableist plain reading of it!"