When we spoke with John Flansburgh in 2011, he explained what this song is all about. Said John: "There's an old Parker Brothers racehorse game called Derby Day. It's like the people that made Monopoly sort of failed in an attempt at doing a race game with dice. And there's six horses and one of them is actually named Hot Cha. And I don't think as a kid I even knew what Hot Cha was. It's basically just a jazz expression. So it's like a horse name - you know the way when you're watching the Kentucky Derby, all the horses have names that aren't names? Well, Hot Cha is the really typical horse name, because it's not really a name. And this is a game that we actually had at my grandparents' house. So the song has sort of got a prodigal son thing about it. Just thinking about families and so it was just part of my deep childhood background, and that was just the basis of it. On the surface it doesn't seem to make any sense. But it really is about sort of a character named Hot Cha and that image comes directly from my own family."
While the song's title came from a board game, we asked John if the song was inspired by a family member. He replied: "I think it's about wandering kids in general. I mean, it really is a character song. But the detail was drawn from my own family. I mean, I think it's sort of a mystery song. Nobody in my family is that big a mystery."