Sarah Silverman recently shared a jaw-dropping anecdote from her time at the Saturday Night Live 50th anniversary celebration, revealing a bizarre and risqué wager she made with fellow comedian Jon Lovitz. The revelation came during her appearance on Late Night with Seth Meyers, where the two former SNL colleagues reminisced about the star-studded event.
The story unfolded as Silverman, now 50, described the atmosphere at the anniversary special, which brought together legendary cast members and guests from throughout the show's history. As Paul McCartney prepared to take the stage for his performance, Lovitz, 68, leaned over to Silverman with an unusual proposition that caught her completely off guard.
According to Silverman's account, Lovitz proposed a straightforward yet shocking bet: "If I can guess what song he's gonna sing, will you show me a picture of your vagina?" Without hesitation, Silverman accepted the challenge, responding with a definitive "Absolutely. Deal." The audience at Meyers' show gasped and laughed as Silverman recounted the bold exchange between the two comedy veterans.
Lovitz's musical intuition proved remarkably accurate. He correctly predicted that McCartney would perform "Golden Slumbers", the beloved track from The Beatles' iconic 1969 album Abbey Road. As the opening notes of the song filled the venue, Lovitz turned to Silverman with triumphant satisfaction, declaring, "I knew it! A bet's a bet!"
Seth Meyers, who was seated alongside both comedians during the performance, provided his own perspective on the incident. The 52-year-old talk show host admitted he was completely unaware of the wager taking place right next to him. "From my vantage point, I did not know this had happened," Meyers explained. He described watching Lovitz turn to Silverman with evident excitement, though he couldn't hear their whispered conversation over the music.
It wasn't until later that Silverman revealed the details of the bet to Meyers, who immediately recognized the story's comedic gold. "And you told me, and I'm like, 'This is the best story,'" Meyers recalled, appreciating the perfect combination of celebrity, absurdity, and old-school SNL camaraderie.
Silverman notably left out one crucial detail from her retelling: whether she actually honored the terms of the bet. The comedian declined to specify whether she followed through and showed Lovitz the promised photograph, leaving that particular question unanswered and allowing the mystery to add another layer of humor to the already outrageous tale.
The three comedians share a common bond through their respective tenures at NBC's Saturday Night Live, though their experiences span different eras of the legendary sketch show. Jon Lovitz served as a cast member from 1985 to 1990, earning two Primetime Emmy Award nominations for his memorable characters and performances during what many consider a golden age for the program. His contributions to SNL helped define the show's voice throughout the late 1980s.
Seth Meyers enjoyed an even longer run with the series, spending 13 years as a cast member and head writer. His tenure culminated in winning an Emmy Award for Outstanding Original Music and Lyrics in 2011, recognizing his work on the show's musical parodies and original compositions. Meyers' time at SNL established him as one of the program's most influential writers and performers before he transitioned to his successful late-night hosting career.
Sarah Silverman's SNL journey was notably brief but significant. She worked as a writer and featured player during the show's 19th season, from 1993 to 1994. Despite her short time on staff, Silverman has maintained connections with the SNL community and expressed gratitude for the opportunity to be part of the institution's legacy. Her experience, though limited compared to some of her colleagues, still earned her a place at the anniversary celebration among the show's most celebrated alumni.
The SNL 50th anniversary event itself represented a landmark moment in television history, bringing together decades of talent to celebrate the sketch comedy institution's enduring impact on American culture. For Silverman, being included in the festivities was particularly meaningful given her brief tenure. She described the experience as "amazing," emphasizing how special it felt to be recognized as part of the SNL family despite only spending one season with the show.
Both Silverman and Meyers expressed particular enthusiasm about sharing the moment with Lovitz, whom they clearly admire as a comedy legend. They described sitting with him at the celebration as "a dream come true," highlighting the respect and affection that exists among comedians who have passed through the SNL ranks, regardless of when they served on the show.
The anecdote serves as a perfect example of the irreverent, boundary-pushing humor that has long defined both SNL and the comedians it produces. The casual outrageousness of the bet, combined with the star power of Paul McCartney and the historic nature of the event, creates a story that encapsulates the unpredictable spirit of live comedy and the unique relationships formed in the high-pressure world of sketch television.
Silverman's willingness to share such a personal and provocative story on national television demonstrates her commitment to the unfiltered, honest comedy style that has made her one of the most distinctive voices in the industry. Her ability to transform an awkward private moment into public entertainment showcases the skill that has sustained her career for decades.
The comedian's latest project, PostMortem, premiered on Netflix in May 2025, continuing her tradition of provocative and thought-provoking stand-up specials. The special, like her appearance on Meyers' show, reinforces her reputation for tackling taboo subjects with intelligence and fearless humor.
This revelation adds another memorable chapter to the extensive lore surrounding Saturday Night Live's behind-the-scenes culture. The show has long been known for fostering close, sometimes outrageous relationships among its cast and crew, who navigate the intense creative pressure through humor that often pushes conventional boundaries. Silverman's story fits perfectly within this tradition, offering fans a glimpse into the unfiltered interactions that occur when comedy legends gather to celebrate their shared history.
The combination of McCartney's legendary status, Lovitz's audacious gamble, and Silverman's game acceptance created a moment that perfectly captures the unpredictable magic that has kept SNL relevant for half a century. It's a reminder that behind the polished sketches and famous faces lies a community of performers who understand that comedy often thrives in the most unexpected and inappropriate moments.