An Exhausted Parent’s Guide to the Top 10 Musical Guests on Sesame Street

A sleep-deprived guide to music and monsters

sesame street music moments
Adam Sandler, Janelle Monáe, and Feist on Sesame Street (PBS)

    The pandemic has offered us many flavors of hell, but one particular torture is reserved for working parents of small kids. For many of us, a COVID-19 exposure doesn’t just mean days of nasal swabs and low-grade anxiety, it means we’re suddenly isolated; cut off from childcare and trapped during business hours with a tiny, lovable demon.

    It seems to happen in my household at least every other month, and in an act of desperation we have turned to the furry monsters of Sesame StreetElmo in particular has become a third co-parent, and there are times when I love him more than my wife.

    Led by my 13-month-old, I have watched hundreds of hours of Sesame Street. Not full episodes, of course; if I’m on a call, I can’t risk one of those meandering animations that always seem to plod across the screen as soon as it’s my turn to talk. So as a compromise between what I like — music — and what he likes — Elmo — we have burned through clips of Sesame Street‘s musical guests, taking in everything that YouTube has to offer.


    What follows is a practical parent’s guide to monsters and popular music. I write it not as a music critic, but as an exhausted father who has learned through trial and error which videos are worth five minutes of peace.

    I say “videos,” because this exercise is about visual delights as much as songs. Some of the finest musical moments in Sesame Street‘s history — from Ray Charles teaming up with Bert and Ernie, to Johnny Cash serenading Oscar the Grouch with “Nasty Dan,” through Yo-Yo Ma’s epic collaboration with the Honkers — are too subtle for my one-year-old, and left him toddling to the kitchen to turn all the knobs on the stove.

    I’m not here to apologize for his awful musical taste. This is a kid who tries to eat dirt, okay? We’ve got bigger problems. Instead, let’s give the little people what they want: elaborate puppet musical sequences shot with all the flair of a midcentury MGM musical.


    The next time you need to take a work call, unload the dishwasher, or just have a good cry in the bathroom, here are the top 10 videos to try.

    10. Destiny’s Child: “A New Way to Walk”

    The vast majority of Sesame Street musical guests perform rooted to one spot in front of a green screen, and these clips are almost all of questionable valuable to the exhausted parent. Destiny’s Child manages to break the stand-still curse with help from Zoe, Grover, and Elmo, who put on a clinic in pedestrianism the likes of which hasn’t been seen since Monty Python’s “Ministry of Silly Walks.”

    To top it all off, Michelle, Kelly, and Beyoncé are performing a Sesame Street classic first made popular by The Oinker Sisters. Younger viewers may be especially tickled by the monsters’ habit of suddenly leaping into frame like a high-speed game of peek-a-boo.

    09. Dave Grohl: “Here We Go Song”

    Another green screen clip, but this one has the frenetic editing of a top-rotation MTV music video. Dave Grohl’s interests turn out to be a natural fit for Sesame Street, and a song about his two favorite pastimes — making friends and hitting the road — provides an opportunity for a rocking travelogue. Alongside lead guitarist Elmo and tambourinist Big Bird, Grohl belts out “Here We Go” in deserts, mountains, cities, and rocky beaches. Watch it a few dozen times, and good luck getting those “la la la las” out of your head.

    08. Hailee Steinfeld: “I Wonder, What if, Let’s Try”


    Hailee Steinfeld was nominated for an Oscar for her work in True Grit and enchanted audiences around the world as Gwen Stacey in Spider-Man: Into the Spiderverse, but this still stands as one of her greatest creative achievements. The thing that makes “I Wonder, What if, Let’s Try” so endlessly rewatchable is that Sesame Street itself is the star.

    Steinfeld paces back and forth in front of the iconic storefronts, as Elmo and Rosita attempt to build a tower even after running out of blocks. There are cameos from half a dozen monsters, and to add to the magic of the moment, butterfly puppets are constantly flitting at the edges of the screen. For this one, Sesame Street put their money where their monsters are.

    07. Jason Mraz: “Outdoors”

    Personally, I had my fill of Jason Mraz’s “I’m Yours” shortly after it dropped in 2008, and I didn’t initially find it much more charming repurposed as “Outdoors.” Chalk up this ranking to my young co-critic, who hyperventilates with excitement as soon as he hears that reggae-inspired guitar. Besides, this has to be one of the most elaborate musical performances ever filmed on Sesame Street. There are multiple locations, a host of extras playing hopscotch, hoola hoop, and pat-a-cake, and of course, puppets galore. Be careful, though: That refrain, “Let’s go outdoors,” might hit a bit too hard if you’re stuck inside working through it.

    06. Maggie Rogers: “It’s Nighttime”


    Some children enjoy sleep, or so I’ve been told; my dude throws a 3:00 a.m. rave in the crib every night. So while I have no evidence that “It’s Nighttime,” will help put a child to bed, I can tell you that it captures the magical possibilities of the sun going down. Raccoons raid Oscar the Grouch’s trash pile, an owl play sax, and fireflies twinkle enchantingly, as Maggie Rogers spins a tale of nocturnal delights. She bids goodnight to Big Bird and his teddybear Radar, and passes Elmo yawning and clutching Baby David. “It’s Nighttime” is as warm and pleasant as a dream.

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