Snoop Doggy Dogg? Bob Barker? David Brenner? — Smithers, “Two Dozen And One Greyhounds”
Mr. Burns likens Li’l Monty to actor Rory Calhoun, who starred in dozens of Westerns throughout his silver screen career. This won’t be particularly educational, but I just want to show you a screenshot I took of his Wikipedia page a few seconds ago:
I didn’t do it.
Anyway, it’s hard to say why Burns/the Simpsons writers chose Calhoun as the representative stander/walker, but I’d wager it would have something to do with the actor’s lanky profile, which makes him appear as if he’s just barely holding his balance. Such as this shot from the 1965 flick Apache Uprising (in which his character’s name is actually Jim Walker):
Calhoun’s the one without a hat. Repeat: hatless.