Sunday Night Sondheim: Anyone Can Whistle – Cleo Laine

Though I don’t get her leopard “jumpsuit” or some of the staging, Cleo Laine really gives us a wonderful performance with this somewhat obscure song from a rarely produced Stephen Sondheim show with the same title: “Anyone Can Whistle”  Below the video I’ve attached several YouTube comments that are quite informative and insightful.

Question: I adore Sondheim and his work, and almost always understand it (even the most complex) but for some reason I never understood this song. Any explanations?

The character in the musical (Anyone Can Whistle) is singing about how she can do hard things without problem or error, but the simple things she wishes she could do, she cannot. "What’s hard is simple, what’s natural comes hard." She’s unable to let go of her troubles and she wishes someone could show her how to do that.

From what I read the song is allegorical to the composer’s own insecurities. How many other songs deal with this subject? A masterful yet simplistic and touching song.

I agree. I love it, it’s a shame that it’s so obscure.
I believe it’s about how for somewhat uptight people like Faye (the character), the most challenging things in life (dancing a tango, reading Greek) come natural to them because it actually requires heavy thinking. But an act as easy as whistling (which anyone can do), Faye can’t do it because all it requires is carefree-ness.

and of course whistling is also a metaphor for that simple thing of falling in love which she also finds hard even though she’s desperate to. such a wonderful way of putting it!

Makes me feel like shes packing up to go, maybe begin another life, another time and place, or leaving to go be herself and wander. Gives me hope somewhat in knowing so.