The Grammy-nominated Americana singer-songwriter takes a look at Willie's #1 country hit from 1980, "Angel Flying Too Close to the Ground," a topic that prompts her to do some deep thinking on the difference between writing a sad song and feeling the need to just sit and listen to one. From there, she goes on to describe what it was like to record a duet with Willie on one of her own sad songs, “Learning to Lose"—and then offers up one of Willie’s favorite dirty jokes.