Stephen Sondheim is perhaps the greatest teacher of all, hiding pearls of wisdom throughout his lyrics that offer uniquely sage perspectives on the world. Now, I am not suggesting that you should adopt all of the philosophies within his musicals, as Sweeney Todd and Assassins might serve as a ticket to prison, but there are some songs that just so perfectly capture the lessons of life that they deserve to be committed to memory for the wisdom they impart. So, today’s “Top-Ten List” will feature my favorite “Stephen Sondheim Songs to Live By.” 

Top Ten Stephen Sondheim Songs to Live By

1. “Ya Gotta Get a Gimmick” from Gypsy

Granted, he only provided the lyrics for Gypsy, but what an amazing bunch of lyrics they are. This song has always been a testament to me about the importance of finding you individuality and that unique “something special” that sets you apart from the rest of the world. Even in the world of a stripper, you have to cultivate your personae. It’s an important lesson for all of us to remember that you don’t necessarily have to get naked to take your clothes off. “If ya gotta bump it”, folks, “bump it with a trumpet” that lets people know who you really are!  

2. “Move On” from Sunday in the Park with George

How easily do we get mired in the problems and challenges of life? People will always criticize you, even during the greatest of your achievements. “Stop worrying if your vision is new. Let others make that decision; they usually do” stands out as a sage bit of advice, made all the more wise by the addendum “You have to move on.” Life is about moving forward, regrouping after defeat, and not becoming complacent through success. Keep making those choices. “I chose and my world was shaken…so what? The choice may have been mistaken, but the choosing was not.” If ever you find yourself second-guessing yourself like the artist George in Sunday in the Park with George “Just keep moving on.”   

3. “Someone in a Tree” from Pacific Overtures

Perspective. Everything in life is a matter of perspective. Different points of view come together to shape and mold events, and perception of those events is how history is interpreted and recorded. Time also shapes how we look at the events in our life, shaded by our evolving maturity, colorful embellishments we like to employ, and even perhaps by our mood at the time. In the musical Pacific Overtures, the song “Someone in a Tree” reminds us that everyone experiences and relates a situation differently. A treaty between Japan and the United States unfolds, as it is witnessed by three men: a young boy watching from a tree who only sees the action, an elderly version of himself who recalls the event from his youth, and from the perspective of a shogun warrior who is hiding under the treaty house, giving the audio interpretation without any visuals.    

4. “The Miller’s Son” from A Little Night Music

“There are mouths to be kissed before mouths to fed” relates the intentions of a saucy maid who imagines all of the possible paths that her life could take, resolving that there is time enough for settling down, but that she prefers to experience every moment before she must. Grab every scrap of pleasure and happiness that you can find. Remember: “It’s not much of a stretch to the cribs and the croup, and the bosoms that droop and go dry.”    

5. “The Miracle Song” from Anyone Can Whistle

In Anyone Can Whistle, a town has gone bankrupt and the mayoress will do whatever it takes keep it afloat. When a leaky drainpipe gives the illusion that water is coming from a rock, she decides to promote the civic mess as a “miracle”. Soon, the town is thriving when busloads of tourists come to “take the waters” for their healing qualities. It’s all quite absurd, but the song reminds us that, with a little ingenuity and imagination, we can repaint sewage to look like magic. I take these lyrics less literally, but rather as a metaphor for finding the positives in even the crappiest situations.    

6. “No One Is Alone” from Into the Woods

Despite its softening in the recent film version, “No One Is Alone” is a haunting song from Into the Woods that is less about solidarity, and more about taking caution. Let us remember its most shiver-inducing lyric “Careful, no one is alone.” It’s true. For all of the people who are on your side, who believe in your cause, and make you feel safe and cozy, there are opposing forces in this world that work against us, oppose you, and make you lay in bed at night, shaking with fear. Okay…possibly a bit of hyperbole on the last part, but this is a reminder to be careful of who you trust and to not trust blindly. There are those who will pretend to be your friend, those who work as agents for the opposing forces in your life. Ward off negativity with vigilance. Choose your inner circle wisely.   

7. “Beautiful” from Sunday in the Park with George

Never has a moment in a musical made me weep more uncontrollably than when Barbara Bryne, as the “Old Woman” in the original production of Sunday in the Park with George, sang this achingly heartfelt number about change, followed by the spoken line “Oh Georgie, how I long for the old view.” It’s a song that reminds us not take things for granted, for us to enjoy the view while we still have it. “Sundays…disappearing…all the time. When things were beautiful.” Don’t we recall our youth with a bitter sweetness that makes us long for the idealistic blanket we’ve wrapped it in?   

8. “I’m Still Here” from Follies

Aging vaudevillian Carlotta Campion sings this song of resilience, reminding us that “good times and bum times, I’ve seen them all and my dear, I’m still here.” Life is a rough journey, and for most of us it will not be a ride down a smooth, straight highway. Better to fasten that seatbelt and take the ride with the idea that you will make it to that finish line with bumps, scrapes, and emotional scars. Through determination and reinvention, Carlotta finds ways to endure the trials and tribulations of her journey, and we can all do the same. It’s called “weathering the storm” and this song will cheer you on. “I’ve run the gamut, A-Z. Three cheers and dammit, C’est la vie. I got through all of last year, and I’m here. Lord knows at least I was there, and I’m here.”  

9. “Children Will Listen” from Into the Woods

Not enough credence is given to the influence we have on children, and this song so gently cautions us to remember the domino effect our words and actions have. “Careful the things you say, children will listen.” In a day an age where parents strive to be their child’s best friend instead of role model and parent, this advice becomes doubly important. It is the examples and expectations we set that create the adults of tomorrow, so choose your words and actions wisely. The children you raise are the adults society will someday have to endure. Shape them into productive, proactive, empathetic people who will bring positive change to the world. “Careful the spell you cast, not just on children. Sometimes the spell may last, past what you can see and turn against you.” 

10. “Now You Know” from Merrily We Roll Along

This song may just include my favorite set of Sondheim lyrics ever. Life is messy. There is no getting around that. We have been filled with so many Disneyfied promises of “Happily Ever After” and this notion that we are all deserving of having what we want is just not realistic. For most of us, we will get kicked down, again and again. There is something liberating in realizing this and then moving on (See “Move On”). 

“It's called flower's wilt, it's called apple's rot
It's called thieves get rich and saints get shot
It's called god don't answer prayers a lot
Okay, now you know…

Okay, now you know, now forget it
Don't fall apart at the seams
It's called letting go your illusions
And don't confuse them with dreams…

Because now you grow
That's the killer, is
Now you grow” 

And we do grow from our failures, mistakes and losses. In fact, it’s those negatives that often prepare us to receive success and happiness when it does arrive. The song isn’t insinuating that you shouldn’t be an optimist or hope for the best, it just reminds us that we make better choices with realistic expectations and we temper our dreams with an equal dose of reality. Life is about balance. 

And this is some of the Sondheim wisdom that regularly resonates with me. For those who call it “cynical” I would reply “practical.” After all, “There’s a whole in the world like a great black pit and it’s filled with people who are filled with…”