The Best, Worst, and Funniest Moments From SNL‘s 50th Anniversary Special

Saturday Night Live (SNL) has been a staple of American television for over 50 years, delivering countless moments of laughter, satire, and unforgettable sketches. Its recent 50th Anniversary Special was a celebration of the iconic show’s enduring legacy. The special, aired on February 17, 2025, featured an all-star cast of former and current cast members, beloved guests, and legendary musical performances. But like any milestone event, it had its share of brilliant moments, awkward stumbles, and hilarious surprises.

In this article, we break down the best, worst, and funniest moments from SNL's 50th Anniversary Special that had fans laughing, cringing, and reminiscing about decades of comedic genius.

1. The Best Moments: Star-Studded Highlights and Emotional Tributes

The SNL 50th Anniversary Special was packed with jaw-dropping performances and heartwarming tributes to the many talented people who helped shape the show’s history. Among the standout moments were appearances from original cast members like Dan Aykroyd, Bill Murray, and Gilda Radner (through a heartfelt tribute), and musical performances from Paul McCartney and Sabrina Carpenter. These segments made it clear why SNL has stood the test of time as one of the most influential sketch comedy shows in television history.

One of the most emotional moments of the night was the tribute to the late great cast members, including Gilda Radner, Chris Farley, and John Belushi. A montage of their best moments from the show had fans reaching for tissues, and many celebrities shared heartfelt anecdotes about the impact these performers had on their own careers. The touching tribute to these legends was a reminder of how deeply SNL shaped the entertainment industry and provided a platform for the most talented comedians of their generations.

Another stand-out moment was the reunion of the "Not Ready for Prime Time Players," the original SNL cast members. The reunion felt like a celebration of everything the show has been and continues to be. The cast took the stage together for an impromptu sketch that had the audience laughing from start to finish. Seeing these legendary performers back together brought both nostalgia and an undeniable sense of joy to the event.

And of course, SNL wouldn’t be SNL without its musical guests, and this anniversary special delivered in spades. Paul McCartney performed a surprise set that had the crowd on their feet, reminding everyone why he’s still considered one of the most influential musicians of all time. His performance was a perfect blend of nostalgia and fresh energy, marking an iconic moment in the anniversary special.

2. The Worst Moments: Missed Opportunities and Awkward Segments

While the special certainly had its fair share of amazing moments, there were some segments that left fans scratching their heads. SNL’s 50th Anniversary Special aimed to be a celebration of the show’s legacy, but there were moments that seemed to miss the mark or failed to land as expected.

One of the most disappointing moments was an over-reliance on digital sketches, which didn’t translate well to the live format. While SNL is known for its quick-paced, sharp-witted humor, some of the pre-recorded segments, particularly a digital sketch poking fun at the current political climate, felt forced and lacked the spontaneity that the show is known for. These sketches were supposed to bring laughs, but instead, they fell flat, leaving the audience looking around in confusion.

Another misstep came in the form of the "tribute" to the show's history, which featured a segment where current cast members impersonated iconic moments from past sketches. While the impersonations were technically impressive, they lacked the charm and originality that made the original sketches so memorable. Instead of paying homage to the legendary skits that defined SNL, these re-creations felt like pale imitations, and in some cases, even seemed to mock the original performances. The lack of genuine heart in this tribute left some viewers feeling underwhelmed.

A more awkward segment involved a brief cameo by a celebrity guest, whose humor was based on outdated pop culture references that did not resonate with the younger audience tuning into the special. This moment caused the show to momentarily stumble, as it was a jarring departure from the fast-paced humor and sharp wit that SNL is known for. In a show that has always been a mirror of the times, this attempt at revisiting older references felt more out of touch than nostalgic.

3. The Funniest Moments: Classic Skits, Unexpected Guests, and Hilarious Reunions

Despite the few misfires, the funniest moments of the night were undeniable, bringing the audience back to the heart of what makes SNL great—timeless humor that speaks to the cultural moment.

Perhaps one of the most beloved segments was a reunion of the "Weekend Update" anchors over the years. From the deadpan delivery of Chevy Chase to the sharp wit of Tina Fey and Amy Poehler, the Weekend Update segment brought together some of the show’s best anchors for a roundtable discussion of current events. The quick banter, hilarious commentary, and zinger-filled exchanges reminded viewers of how important the segment has been to SNL’s legacy. The moment was made even funnier by the occasional teasing and playful jabs between former hosts, reminding everyone that while the format might change, the heart of Weekend Update remains unchanged.

Another funny moment came courtesy of former cast member Will Ferrell, who reprised his iconic role as Alex Trebek on the game show Celebrity Jeopardy! This segment was a fan favorite, as Ferrell’s hilarious portrayal of the quirky game show host brought the house down. In true SNL fashion, the sketch was filled with unexpected twists, including a surprise appearance by a former Jeopardy! contestant who didn’t quite know the answers (and definitely didn’t get any questions right).

The special also had a hilarious musical segment that poked fun at the evolving nature of pop culture and social media. With the help of current SNL cast members, former guest performers, and some surprise cameos, the show cleverly mixed satire with catchy tunes to highlight how much things have changed since SNL’s inception. From “gramming” to TikTok trends, the playful commentary on modern internet culture had viewers of all ages laughing in recognition.

Speaking of surprise cameos, one of the funniest moments of the night involved a random, unexpected cameo by SNL legend Adam Sandler. Sandler appeared on stage for a sketch that mocked his own rise to fame and the bizarre, often chaotic, nature of his career. The sketch had fans in stitches, as Sandler’s self-deprecating humor and ability to laugh at his own legacy was both endearing and hilarious. The sketch was a reminder of the kind of unique humor that Sandler brought to SNL during his time on the show, and his return was one of the special’s true highlights.

4. Final Thoughts: A Night to Remember, but Not Without its Hiccups

Overall, SNL's 50th Anniversary Special was a night full of laughter, nostalgia, and unforgettable moments. There were some obvious stumbles, from awkward sketches to misfired tributes, but these moments were few and far between. The best moments of the night—whether they were heartfelt tributes, hilarious reboots of classic sketches, or surprise guest appearances—reminded us of why SNL has endured for so many years.

The special brought together the best of the past and present, celebrating the show’s incredible impact on pop culture, comedy, and television history. From the star-studded lineups to the iconic sketches, the 50th Anniversary Special was a fitting tribute to a show that has defined American comedy for half a century.

As fans continue to reminisce about the hilarious, the awkward, and the downright unforgettable moments from the special, one thing is clear: SNL’s legacy is as strong as ever, and the show’s ability to stay relevant after 50 years is a testament to its place in the hearts of viewers. Here's to another 50 years of laughs, satire, and timeless moments that will continue to define the landscape of American comedy.