Sesame Street: 10 Best Celebrity Guest Stars Of The Last 50 Years, Ranked

In its iconic 50 year run, Sesame Street has featured some amazing celebrity guest stars. We review the top ten stars who visited the Street.

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It’s not every day that a series runs for 50 consecutive years on television. In fact, that’s more or less unheard of these days. But the beloved children’s television program Sesame Street has managed to achieve just that, spreading joy and educating children all over the world for 50 years. Featuring everyone’s favorite adorable Muppet friends, lively songs and sets, and an incredibly talented cast of human performers, too, Sesame Street has remained absolutely vital and relevant television, adapting to the times and tackling important, and sometimes difficult, topics in children’s education.

Along the way, Sesame Street also made a name for itself in terms of recruiting an amazing amount of celebrity talent to appear on the famous Street. Over the decades, literal hundreds of celebrities have appeared on the series, whether as themselves, as fictional characters, or even as their own Muppet counterparts. With that said, this list could therefore run on forever. But here, we tried to narrow it down to ten of the best celebrities to ever appear on Sesame Street. Here’s who made the cut.

10 Adam Sandler

The years have shown that some of the best people to interact with Muppets are professional comedians. By far one of the most natural of them all is Saturday Night Live star turned movie star Adam Sandler. Sandler has had a couple of appearances in recent seasons of Sesame Street, one of which made use of his gift for comedic songwriting and storytelling.

Sandler first appeared in the 41st season, defining the word “crunchy” in a skit with a very noisy Cookie Monster. Sandler later appeared in the 42nd season of Sesame Street, serenading everyone’s favorite fuzzy red Muppet in “A Song About Elmo.” The song works to create charming rhymes for the word Elmo, and features guest appearances by other Muppet creatures including a lively dragon and a parrot.

9 B. B. King

Sesame Street is also well-known for having some incredibly iconic musicians among its expansive cast of guests. Far and away one of the most famous of these such guest stars is the legendary blues artist B. B. King. The King of the Blues appeared multiple times throughout Sesame’s lengthy tenure, and his own impressive, expansive career. Every time he appeared, he was as engaged, as lively, and as perfect as he ever was.

All the way back in Sesame’s first season, King sings the alphabet with Sesam e Street resident Susan. He later appeared in season 15, performing “Alphabet Blues” and “Count to Ten.” But perhaps his best performance of all came in season 32, when he joined together with a group of B-named Muppets to sing an ode to the letter B.

8 Whoopi Goldberg

Few celebrities have had quite as lengthy a relationship with the Muppets and Sesame Street as cultural icon Whoopi Goldberg has. “Any time the Muppets are working, I always tell the puppeteers I want to come and play,” Goldberg wrote in 2011 of her long relationship with the beloved puppets. Based on the sheer volume of her Sesame appearances, that definitely seems to be true.

Goldberg first appeared in season 22, taking part in a skit with Elmo discussing the importance of loving your own hair, your own skin, and yourself. She took part in the music video for the iconic song “Monster in the Mirror,” appears as a fairy godmother to Prairie Dawn, and discusses dealing with emotions like anger with Baby Bear. Whoopi Goldberg has been a reliable voice and face throughout Sesame’s history, earning her a spot on this top countdown.

7 Ray Charles

Ray Charles was one of the most well-respected musicians of his time, with a voice so distinct and a talent so deeply amazing and moving that it was impossible to not be mesmerized by his performances. He also had an infectious joy and warmth to him, too, as evidenced by his many appearances on the beloved Street throughout its history. Charles appeared on the series as early as 1977’s season nine, and as late as 1996’s season 28.

His appearances were all defined by music, played at his piano with Muppet and child performers surrounding him. He sang songs such as “I Got A Song,” “The Alphabet Song,” “Monster in the Mirror,” and “Oh, What A Beautiful Morning.” Charles even took part in Sesame’s then groundbreaking 20th anniversary celebration, three decades ago.

6 Lin-Manuel Miranda

After his tenure In the Heights and long before wowing the world with Hamilton: An American Musical, Lin-Manuel Miranda began a whole new career as a member of Sesame Street – both in front of and behind the camera. In the series’ 40th season, which premiered in 2009, Miranda plays the villainous Freddy Flapman, a cutthroat real estate agent who wants to convince Big Bird to move off of Sesame Street and into a the more bird-friendly environment of the rain forest.

Beyond his turn on the series, Miranda has contributed considerably behind the scenes, too. He was seminal in the development of the “Murray Has A Little Lamb” sequences, featuring Murray and the little lamb Ovejita, and sings the theme song for these segments.

5 R.E.M.

Another hallmark part of Sesame Street’s 50 year history has been its pitch perfect parody and adaptations of popular culture, whether it’s music, television, or movies. Some of the best examples of these feature popular musicians recreating some of their biggest hits, now with a Muppet twist. One of the best of all of these came in Sesame’s 30th season in 1991.

The iconic rock band R.E.M. appeared on Sesame back in season 30 to perform “Furry Happy Monsters,” a take on their successful song “Shiny Happy People.” During the song, R.E.M. are joined by a female vocalist Muppet as they observe the emotions of Muppets around them, ranging from happy, to sad, and back to glad again.

4 Maya Angelou

While our list has mostly consisted of celebrities from entertainment fields like film, television, and music, one of the most influential Sesame Street guest stars of all time defies those trends of categorization. Maya Angelou, the esteemed poet and Poet Laureate, appeared many times on the groundbreaking series to spread her wisdom through poetry, spoken word, and song.

She educated characters like Herry Monster, Baby Natasha, and Elmo about words beginning with the letter of the day, and their uses. She took part in renditions of iconic Sesame songs including “Sing” and “A New Way to Walk.” And she would even go on to appear in the Christmas special Elmo Saves Christmas in 1996.

3 Stevie Wonder

Sesame Street has had a seemingly endless string of iconic music moments. But none of them will ever quite compare to the pure joy captured by Stevie Wonder’s fourth season appearance on the series in 1972, and his episode-long back and forth with everyone’s cute and furry little friend Grover. Wonder would spend most of the episode teaching Grover about music, and different styles of both playing and singing.

He would also perform a song he’d specifically written just for his appearance, “123 Sesame Street.” But perhaps even more special than that was Wonder’s performance of his then-hit song, “Superstition” – a song that would hardly fit in today’s Sesame universe, but a truly one of a kind performance that stands the test of time as something truly special.

2 Lupita Nyong’o

Sesame has always been an incredibly inclusive series, but perhaps one of their most influential segments, and one that instantly went viral when it premiered, featured the Oscar winning actress Lupita Nyong’o. In season 45, which premiered in 2014, Nyong’o appeared in one of the series’ regular segments, defining a word alongside one of the many beloved furry little friends.

In her case, Nyong’o was tasked with explaining the concept of skin to little Elmo. And much like the Whoopi Goldberg segment so many years earlier, Nyong’o stressed the importance of loving your own skin, offering yet another one of Sesame’s trademark fully inclusive message to all viewers of all ages.

1 Robin Williams

There aren’t many people who could keep up to speed with Muppets, in terms of energy, enthusiasm, flexibility, and speed of speech. But if there was someone who was always up to the task, it was the late, great, legendary Robin Williams. Williams’ appearances on the series spanned from season 27 to season 42, from 1990 to 2012. He was paired with Muppets and children alike, in skits that found him explaining things as different as what it means to be alive and what it means to be in conflict.

He was paired with beloved Sesame Street icons like Elmo and the always feuding Two-Headed Monster, going head to head (to head) with the latter in a truly hilarious segment featuring all of them yelling at each other. He was always game for whatever Sesame had in store for him, even improvising and adlibbing along the way. Sesame Street was truly at its best whenever Williams was visiting.

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