He Sang A Duet With Big Bird
Alright, we know this doesn’t sound “insane” in the sense that the previous stories were, but hear us out.
When it comes to television, you don’t get much more iconic than Sesame Street. So when the show branched out into its first feature film, and Jennings was the only country singer cast, that was a huge deal.
Jennings had a small part in the film. He played an unnamed turkey farmer who picks up a hitchhiking Big Bird. As he drives with his new feathered friend, Jennings offers him some words of wisdom through an undeniably catchy song, “Ain’t No Road Too Long.”
The reason why this small role was such a crazy part of Jennings’ history is because he somehow managed to give a Sesame Street movie some outlaw cred. And it doesn’t hurt that he gave us the perfect road trip song in the process!