A few of the best rock star appearances on Sesame Street

Recently, I wrote a list of the craziest rock star appearances on kids' shows. If you thought there was a conspicuous absence of Sesame Street on that list, that would be because I quickly realized that Sesame Street was its own list.

Sesame Street has quite the cultural cache

This is by no means an exhaustive list, as Sesame Street’s roster of musical guests over the past 50-plus years has just been crazy.

Paul Simon

They say to never work with kids or animals. I guess the reason is because they can be unpredictable. But unpredictability makes for good TV. Especially if that TV show is a showcase of the uniqueness of children’s minds. 

In 1977, when Paul Simon appeared on Sesame Street to perform his 1972 hit “Me And Julio Down By The Schoolyard,” he sat on the famous 123 Sesame Street stoop next to a little girl named Leslie, who improvised her own lyrics. She was more than a little off-key but utterly charming. Simon himself seemed utterly charmed, but at about the 25-second mark, he realizes that he has a job to do and cuts in. 

At that point, the easy-listening song, being performed on a kids' show no less, becomes a battle of wills. At every lull in the lyrics, Leslie cuts back in with her improvisations. If Paul Simon had any heart, then he’d have been highly conflicted about stealing the limelight from Leslie. I guess he had some obligation to get through the song, but frankly, it’s heartbreaking when he has to interrupt her. 

In 1988, Simon recorded a video for the song to promote his greatest hits compilation Negotiations And Love Songs. The video self-deprecatingly played on Simon’s unhip image by having him hang out with high school kids in Hell’s Kitchen. I’d love to believe that Leslie was there somewhere.