The 15 Best Sesame Street Musical Guests

Sesame Street was ahead of its time in so many ways, among them the inclusion of celebrity guests more familiar to parents than kid viewers. By welcoming icons of the stage, screen, and sport to the neighborhood, the show proved it could talk to adults and children at the same time, without talking at either. Their musical guests have been some of the most memorable, with legends showing up to croon on Jim Henson originals and a seemingly endless book of punny parody tunes that might as well have been the original Dad Joke Bot. No wonder you loved that show so much.

If you’re a musician, you haven’t gotten anywhere until you’ve figured out how to get to Sesame Street. Here’s a sampling of the very best of the show’s myriad musical guests to play for your kid, brought to you by the number 15.

Maya Angelou: “My Name”

Whether your kid is named for a movie character, athlete, inventor, or your great aunt Gertie, Dr. Angelou wants them to know: “If you don’t like something, change it. If you can’t change it, change your attitude.” Okay, that’s a lie. She actually sang about how every name is unique and every kid should love theirs. Although an attitude adjustment is also generally welcome.

Ray Charles: “Believe In Yourself”

A classic Sesame Street original, sung by one of the all-time greats. Kids’ TV could use more of this. And less Elmo.

Johnny Cash: “Nasty Dan”

Pairing Cash with Oscar to sing about the meanest man he ever knew (and his nasty old wife and nasty kid and nasty house) was perfect, although it still seems like they missed a great opportunity to teach kids about the color black. Play this for your kid and then watch with pride as they sincerely tell your mother-in-law to “Have a rotten day.”

Destiny’s Child: “A New Way To Walk”

Beyoncé is Queen and Grover’s gonna let you finish, but the original by the Oinker Sisters is the best version of all time.

Wynton Marsalis: “Monster Music Class”

This is somewhere between a sketch and a song as it takes a few minutes for the music to get going, but it’s worth it to watch those honker monsters bash their own faces to that Nawlins beat. They’re almost enough to make you ignore the presence of Fiddle Me Elmo.

Smokey Robinson: “U Really Got A Hold On Me”

Today’s musical guest, Smokey Robinson, was brought to you today by the letter “U” and the number “5.” As in, the “U” in this Motown parody is a real stage-5 clinger.

Feist: “1, 2, 3, 4”

Feist’s catchy as hell pop tune was the most ready-made for Sesame Street since “ABC.” They changed the lyrics anyway, because counting “Chickens just back from the shore” is just a teeny bit more on-brand than “Tell me that you love me more.” Plus, those birdies can sing.

Paul Simon: “Me & Julio”

There’s something really enjoyable about the unscripted, unproduced nature of this early Sesame Street segment. Those kids dance like nobody’s watching because, at the time, they genuinely didn’t know if anyone was. Simon’s tune is perfect for a sing- and dance-along, but it’s obvious who the real star of the show is here. Just let her sing, Paul!

Adam Sandler: “A Song About Elmo”

Agent: “Hey Sandman, you wanna go on Sesame Street and do ‘Hanukkah Song’ except instead of “Hanukkah” everything rhymes with ‘Elmo?’”

Sandler: “Hell-mo yes! WHOOPIEDEEDOO!”

Katy Perry: “Hot N Cold”

Sesame Street doesn’t want your kid to see this song, but you aren’t your kid, now are you?

Yo-Yo Ma: “Jam Session”

There’s nothing to sing or dance along to here, but it’s probably the only time you’ll ever see Yo Yo Ma get visibly pissed off. Sure, it’s barely perceptible, but it happened! Hoot definitely had it coming with that “Overgrown ukulele” zinger. Nobody puts Yo-Yo in a corner.

R.E.M.: “Furry Happy Monsters”

Guess they passed on “These are the shiny happy people in your neighborhood.”

Lena Horne: “Being Green”

Sesame Street has always understood that quality children’s programming isn’t all slapstick and fart jokes. A beautiful song and the perfect voice have just as much impact as a pie to the face … although there is a reason Super Grover wears a helmet.

Hootie & The Blowfish: “Hold My Hand”

Sesame Street was designed to appeal to city kids, which helps explain their apparent obsession with crossing the street safely — even if it costs you your marriage. Still, nobody would have minded if Elmo had been left stranded on the other side. Thanks a lot, Rucker.

Billy Joel & Marlee Matlin: “Just The Way You Are”

They’re grouch groupies, just like you! Remember this one next time your kid acts like a stinking, scowling garbage monster.