Sarah Sherman’s Surprise T-Shirt Steals the SNL Spotlight: Who’s That Face?

Saturday Night Live has long been a platform for unexpected moments, but during the Jon Hamm-hosted episode on April 12, 2025, Sarah Sherman captured everyone’s attention with a peculiar T-shirt that sparked widespread curiosity. Worn during the goodnights segment, the white tee featured a woman’s face with the word “WHY?” in bold blue letters beneath it, leaving viewers puzzled and eager for answers. LateNighter later revealed the woman to be Karen Siff-Exkorn, a name unfamiliar to most, with a story tied to a charitable cause that added depth to Sherman’s bold fashion choice.

Unpacking the Mystery of the “Why?” Shirt

The Sarah Sherman Why Shirt became an instant talking point when Sherman appeared in it during the SNL goodnights, following a star-studded episode hosted by Jon Hamm. The shirt itself is simple yet striking: a white T-shirt displaying a photograph of Karen Siff-Exkorn, a woman with long brown hair and a warm smile, paired with the cryptic word “WHY?” in blue capitals. According to LateNighter, Siff-Exkorn was the winning bidder of an auction item at the “Night of Too Many Stars” event in March 2025, a comedy benefit hosted by Jon Stewart to support autism programs nationwide, where Sherman and other SNL stars like James Austin Johnson, Marcello Hernandez, and Please Don’t Destroy performed.

Sherman had cleverly auctioned off the chance for the winner to be featured on her shirt during a future SNL goodnights segment, a creative fundraising idea that aligned with the event’s mission. Siff-Exkorn, who chose the “Why?” text from a list of options Sherman offered the crowd, is a board member of NEXT for Autism, the organization behind the event. Her involvement in autism advocacy, including authoring The Autism Sourcebook after her son’s diagnosis, added a meaningful layer to the shirt’s appearance, transforming it from a quirky moment into a subtle nod to a vital cause.

Sherman’s Playful Activism Meets Comedy

Sarah Sherman, known for her surreal and boundary-pushing humor, often uses her platform to blend comedy with unexpected statements, and the Why Shirt is a perfect example of this approach. The choice of “WHY?”—selected by Siff-Exkorn—invites viewers to ponder its meaning, whether as a playful challenge, a reflection on autism advocacy, or simply a nod to Sherman’s love of absurdity. The shirt’s appearance on SNL, a stage watched by millions, amplified NEXT for Autism’s visibility, aligning with Sherman’s knack for embedding deeper messages within her chaotic comedic style, as seen in her past sketches like “Meatballs” and “Chucky.”

Beyond the humor, the shirt underscores Sherman’s willingness to use her platform for good, spotlighting Siff-Exkorn’s work with NEXT for Autism, which has funded over 380 projects across 37 states in the past 20 years. This moment also reflects Sherman’s unpredictable nature—she’s the “queen of the 10-to-1 slot” on SNL, known for late-night sketches that flirt with chaos, as noted by Paste Magazine in 2024. By wearing the shirt, Sherman not only honored a charitable commitment but also reminded us of comedy’s power to provoke thought, spark conversation, and support meaningful causes, all while keeping us guessing about her next move.