8 Famous Musicians Who Appeared on ‘Sesame Street’

Sesame Street was a trailblazer when it first aired in 1969 and became one of the very first children’s shows aimed at both education and entertainment. Over the ensuing decades, with the help of master puppeteer Jim Henson, the beloved series has done just that—enthralling generations of kids while making learning fun. One testament to its popularity and quality is the number of impressive guest stars who've appeared on it. This list remembers some of the most memorable musicians ever to feature on the Street.

1. Paul Simon
2. Linda Ronstadt
3. Ray Charles
4. Johnny Cash
5. B. B. King
6. Cyndi Lauper
7. Stevie Wonder
8. Alison Krauss & Union Station 

Paul Simon

The supremely gifted singer-songwriter Paul Simon taped several performances for the 1977 season of Sesame Street, including a charming duet with a young girl called Leslie. They sang Simon’s hit “Me and Julio Down by the Schoolyard,” and Leslie enthusiastically improvised her own lyrics. The singer also played the Simon & Garfunkel classic “El Condor Pasa” (later covered for The Muppet Show by Gonzo and his chickens!) and “St. Judy's Comet.”

Linda Ronstadt

Across her lengthy career, country, folk, and pop musician Linda Ronstadt has earned more than enough awards to make any trophy cabinet buckle, including no fewer than eleven Grammys. Ronstadt made her Sesame Street appearance during the show's 20th season, which ran from 1988-89, and sang two Mexican mariachi numbers: “La Charreada,” alongside Elmo, and “Y Andalé,” with a full mariachi band. 

Ray Charles

The soul legend made many visits to Sesame Street across the decades, beginning in 1977 with renditions of “Ray Charles Alphabet” and “Oh, What a Beautiful Morning” (the classic ballad from Oklahoma!). The following year he returned to perform “I Got a Song” as part of a trio with Ernie on drums and Bert on guitar. It was then a long wait until 1989, when Charles featured for a wonderful take of “Bein' Green” with the help of assorted Muppets. In 1991, Charles sang “Monster in the Mirror” for the show. His final appearance came in 1996 and included “The Alphabet Song” and Sesame favorite “Believe in Yourself” with Elmo and others.

Johnny Cash

The Man in Black met his match in Oscar the Grouch back in 1973, when the famed country star dropped by the street to perform his song “Nasty Dan.” Longtime Sesame Street composer Jeff Moss penned the number, which later appeared on The Johnny Cash Children's Album. In Cash and Oscar's fantastic skit, Cash sings about Dan's terrible behavior, much to the Grouch's approval, ending the tale with Dan in a state of “nasty happiness” with his nasty wife and nasty kid. "Aren't you Johnny Trash?" asks Oscar. “Have a rotten day,” quips Cash before walking away. The singer returned in 1991 to sing a special version of his hit, “Don't Take Your Guns to Town.”

B. B. King

The great blues guitarist is another star who made several appearances on the street, with his first coming in 1970, when he sang the alphabet. It wasn't until 1984 that King featured again, performing “Alphabet Blues” in Episode 1914 and “Count to Ten” in Episode 1961. There followed another lengthy gap before the guitarist starred again in 2001, alongside Bert, Benny Rabbit, Big Bird, and Baby Bear, to sing about the letter "b". 

Cyndi Lauper

In 1996, the iconic pop superstar Cyndi Lauper brought her flamboyant style and vocal prowess to the street. She played the character Twyla for “Elmocize,” a Sesame Street special in which she sang a “fitness” song that had the distinction of introducing two new puppet characters: the Twister Sisters. Aside from the cute kids and wildly dancing Muppets, what makes this so memorable is Lauper's total commitment to her role.

Stevie Wonder

Soul royalty paid the Sesame stars a visit in 1973 in the form of Stevie Wonder. This is a particularly noteworthy appearance as, rather than performing a children's piece, the singer and keyboardist played his hit single, “Superstition,” which had only recently reached number one on the Billboard Hot 100. Featured on Wonder's album, Talking Book, “Superstition” was written with the assistance of British guitar virtuoso Jeff Beck. For the Sesame Street show, Wonder and his full band of musicians brought the funk full power!

Alison Krauss & Union Station 

Bluegrass and country legend Alison Krauss popped into the neighborhood in 2004 with her top-class band, Union Station, to deliver a fantastic performance of “Sesame Jamboree,” with the able assistance of the Count and a quartet of dancing chickens. “One, two, three, four, my toes are tapping on the floor,” sang the Count, in a perfect counterpoint to Krauss' mellifluous vocals.