New Drools as Paul Simon Steals the Show

The Saturday Night Live 50th anniversary special was an star-studded blast featuring an abundance of laughter, squeezings of music and five decades of pop culture history. But one moment topped the rest: Paul Simon, the legendary singer-songwriter, teaming up with Gen-Z pop sensation Sabrina Carpenter for a poignant opening performance of his classic hit, “Homeward Bound.” Not only was this crossover a musical high point — it was indicative of the bridge between generations that has kept S.N.L. alive for half a century.

The Opening Act: Paul Simon and Sabrina Carpenter’s Eternal Duet

The three-hour special opened with an unvarnished, acoustic performance of Simon & Garfunkel’s “Homeward Bound,” a song Simon first sang on SNL in 1976, during an appearance with George Harrison. This time around, he was joined by 25-year-old Sabrina Carpenter, whose plaintive harmonies gave a new spin to the 1966 classic.

There was undeniable chemistry between the pair. Simon, now 83, joked about the song’s history: “I performed this with George Harrison on this show in 1976.” In her trademark witticism, Carpenter responded, “Well, I wasn’t born then… and neither were my parents! The crowd exploded in laughter, but the previous mood vanished as their seamless vocals coupled together, because good music will never grow old.

Carpenter, in particular, updated the lyrics for today, substituting the original line, “cigarettes and magazines,” for “airport lounges and magazines” — a minimum change but one that speaks to our own daily world. The show closed with “Live from New York, it’s Saturday night!” line despite it being a Sunday when the show aired. No one seemed to mind.

Why Is Paul Simon Back After All This Time?

Simon’s visit was particularly significant. After retiring from performing live in 2023 because of severe hearing loss, many fans thought they would never get to see him in concert again. But SNL creator Lorne Michaels, a good friend, persuaded him to come back for this milestone. The bond between Simon and the show runs deep: he hosted four times and was a musical guest 13 times, including on the first post-9/11 episode.

“SNL has always been a home for artists that are looking to take risks,” Simon said in a joint interview before the show. “Coming back here… It’s like an old friend.” The show and its winners bridged generations of artists and solidified it as a cultural touchstone with his emotional performance.

A Legacy to Last in SNL History

Simon’s association with SNL goes back to its 1975 debut. He’s been involved in some of the show’s most memorable moments over the years:
1976: Singing “Homeward Bound” with George Harrison.

2001: A moving post-9/11 performance that soothed an aching nation.
2025: Handing the baton to Sabrina Carpenter, an emerging star and future face of SNL.
His return for the 50th anniversary was more than a nostalgia trip — it was evidence of the show’s lasting allure. “Paul embodies the soul of SNL,” Steve Martin said in his opening monologue. “And he’s proof that great art never gets old.”

SNL50’s Star-Studded Lineup

If Simon’s duet was the emotional centerpiece of the night, the special packed in laughs and surprises:

1. Steve Martin’s Monologue: The comedy legend poked fun at what it’s like to try to wrangle SNL alums, saying, “We wanted Bill Murray here tonight … so we didn’t invite him.” Murray later interrupted the Weekend Update segment to roast the show’s history.
2. Paul McCartney’s Grand Finale: The Beatles legend ended the night with a medley of “Golden Slumbers/Carry That Weight/The End,” prompting an audience chant for more.
3. Adam Sandler’s Tribute: Jack Nicholson introduced the comedian, who sang a heartfelt song honoring late cast members, including Chris Farley and Phil Hartman.
4. Miley Cyrus and Brittany Howard: Their anguished rendition of “Nothing Compares 2 U” was a clear highlight.

Closing the Gap: Why Simon + Carpenter Succeeded

It was a masterstroke to pair Simon with Carpenter. Their combined presence is nothing less than emblematic of the show’s storied history, in Simon’s case at 83, and its vibrant future, represented by Carpenter, who made her SNL debut in 2024. Resonating across generations, the collaboration had social media abuzz worldwide minutes after it dropped.

“Working with Paul was surreal,” Carpenter told me after the show. “He’s a legend, and yet he made me feel like an equal.”

The Bigger Picture: The cultural imprint of S.N.L.

More than glitter, SNL50 showcased the way in which the show helped shift comedy and music. From launching careers (Eddie Murphy, Tina Fey) to tackling political satire, SNL has reflected societal shifts for five decades. The special even teased its own misfires, as Tom Hanks hosted a satirical “In Memoriam” of sketches that “aged horribly”.

Final Farewell: An Unforgettable Evening

When the special concluded, dozens of stars filling the stage applauded Lorne Michaels. Simon stood next to Carpenter smiling as the credits came up. It was a fitting farewell to a night that honored legacy, laughter and the wonder of live television.

For longtime fans, it was a gift for Simon to come back. For first-time viewers, it was an introduction to a legend. And for SNL, at least, it was evidence that despite half a century, the show can still pull a surprise.