Cat Stevens: If You Want to Sing Out, Sing Out
In some sense, nearly every song by Cat Stevens feels like advice or a pep talk. His songs are overwhelmingly about searching for your place in the world and are (usually) filled with hope. Here are two of his most literal advice songs. First, the wonderful pep talk that is "If You Want to Sing Out, Sing Out"--one of his most positive, optimistic songs, which is saying a lot--from the classic film Harold and Maude. I'll take the clever suicidal Harold over the clever pregnant Juno any day.
Stevens' songs are all over this film's soundtrack, to the point that they're pretty much a character in and of themselves. It is one of the greatest films, so check it out if you've never seen it. The first time I saw it was actually in high school--literally, in high school. For some reason my junior-year English teacher thought this was an appropriate film to show his students. As far as I was concerned, it was--this had a greater effect on me than Catcher in the Rye ever would. But you can imagine how many kids in the class freaked when Harold and Maude wind up in bed together.
Cat Stevens: Wild World
Next up, the more well-known classic "Wild World." This is really kind of a strange song when you think about it. The narrator has just been dumped; apparently his girlfriend is making her way to the big city. Despite having his heart broken in two, he proceeds to give her advice on what the big bad world is really all about--you could almost read this song as a bitterly sarcastic kiss-off: "You're dumping me? You think you'll find someone better? Okay, sure, go ahead, I hope you make a lot of nice friends out there." Adding to the weirdness of the song is that the verses make plain that this conversation is between two lovers, but the chorus is decidedly old man/young girl. Why the hell does he know so much about the world, yet she's only just setting out to discover for herself?
But this is Cat! I know too well from the rest of his songs that he's not trying to be creepy nor sarcastic. It's just not the kind of nuance that finds its way into his songs. I think he's truly giving his heretofore sheltered ex some heartfelt advice.