'Sesame Street': The Best Musical Guests - Rolling Stone
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10 Best ‘Sesame Street’ Musical Guests

The biggest acts of their day have all sang with the gang

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Ray Charles appears on 'Sesame Street'

Jim Henson Prod. / Courtesy: Everett Collection

Sesame Street has been a television institution since its premiere in 1969, captivating children and adults alike while imparting valuable life lessons through a group of instantly recognizable furry characters. The show has also seen its share of musical guests – some of the best and brightest acts of their day have hung out and sang songs with the gang. Here, through 44 years of programming, are the top 10 musical guests the show has seen.

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Ray Charles
Well all know that Ray Charles was one of the coolest guys around, so it’s even more touching to see him explain his blindness to a curious Elmo. Charles and Elmo then break out into a snappy version of the show’s signature tune, “Believe in Yourself;” watching Charles genuinely enjoy himself while singing a duet with the little red guy would make even the most cold-hearted kid smile.

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Paul Simon
In this early clip, a young-ish Paul Simon sits on Street‘s famous front stoop to perform the samba-inflected “Me and Julio Down by the Schoolyard,” one of the biggest hits from his second solo album, Paul Simon. With its simple chord progression and bevy of amusing lyrics (“The Mama pajama rolled outta bed. . .”), the track sounds like it was tailor made to perform on a children’s television show. Watching the child actors sing along to Simon’s strumming doesn’t hurt, either.

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Billy Joel
Decked out in a pair of ultra-awesome 80’s shades, Billy Joel offers an old piano to everyone’s favorite curmudgeon, Oscar the Grouch. Joel then proceeds to sing a reworked “Just the Way You Are” to Oscar, with support from Academy Award-winning actress Marlee Matlin (why she’s there is a mystery, but it works all the same). By the end of the number, Oscar is emotionally unaffected, which brings the point home – he’s in desperate need of some serious psychiatric help.

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If there was ever a popular song that was made to perform on Sesame Street, it’s Feist’s ode to counting, “1234.”  With the help of a cast of characters, the Canadian singer makes the track a little more about counting and a little less about love. There’s also something inherently magical about the chorus of chickens and penguins singing towards the end of the clip.

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Cab Calloway
If you ever wanted to see a green clarinet player, here’s your chance. In this long-forgotten clip, big band impresario Cab Calloway belts out a rousing version of “Hi-De-Ho,” flanked by a quartet of expert horn players. This was one of a few appearances Calloway made on Sesame Street before his 1994 death.

Johnny Cash

If there’s a more touching clip of Johnny Cash, tell us, because we’re not sure one exists. Here, the man in black, dressed in blue denim, explains the concept of flooding to a construction worker before singing “Five Feet High and Rising.” Belting out a song about potentially drowning doesn’t sound like it would work on a show like Sesame Street, but after watching Johnny chuckle before singing, it makes it all worthwhile.

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Garth Brooks
A rare showcase of country music on Sesame Street, here’s Garth Brooks singing “We Make Music” with a group decked out in Brooks’ signature black cowboy hat. Good thing Brooks’ alter ego Chris Gaines didn’t make an appearance, because, well, it’d be difficult to explain to children why he has an alter ego in the first place.

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Yo Yo Ma
Only on Sesame Street can you see a world-class musician have a jam session with a humongous owl named Hoot. Perhaps even funnier is Yo Yo getting momentarily pissed at Hoot around the 1:10 mark. If they brought this act on the road, we’d be the first in line to score tickets.

Jason Mraz
I’m Yours,” Mraz’s 2008 reggae-tinged hit, is a lovely track that maintained a spot on the Billboard singles chart for well over a year. But seeing it performed on Sesame Street – with its lyrics about about giving yourself fully to someone else – takes that loveliness to the next level.

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Wynton Marsalis
It’s hard to teach a group of monsters, so credit the famed trumpeter for even attempting to impart some musical wisdom on them. Marsalis, a Jazz at Lincoln Center veteran, seems genuinely into instructing how to “attack” an A note on the piano, and watching him tune his trumpet using a character’s nose is funny, too.

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