5 Times Sean Connery’s ‘Celebrity Jeopardy!’ Insults Became SNL’s Greatest Running Gag
Few recurring sketches in Saturday Night Live history have achieved the legendary status of "Celebrity Jeopardy!" The premise was simple: take three clueless, often antagonistic celebrities and pit them against the perpetually exasperated host, Alex Trebek, portrayed by the brilliant Will Ferrell. The true star, however, was Darrell Hammond’s portrayal of the late, great Sir Sean Connery, who turned the game show into a vehicle for crude misreadings, aggressive insults, and a consistent inability to grasp the concept of a question. As of today, December 21, 2025, the sketch remains a timeless masterpiece, a perfect storm of character work and escalating absurdity that cemented its place in comedy lore.
The sketch, which ran regularly from 1996 to 2002 and returned for specials like the SNL 40th Anniversary, became a cultural touchstone. It's a hilarious tribute to both the real Alex Trebek and Sean Connery, who have since passed away, leaving behind a legacy of their own, forever intertwined with these iconic parodies. Here is a look at the character profile and the most outrageous moments that made Darrell Hammond’s Sean Connery Alex Trebek’s arch-nemesis.
The Profile of Alex Trebek's Arch-Nemesis: Sean Connery (as Portrayed by Darrell Hammond)
The comedic genius of the Celebrity Jeopardy! sketch lies in the stark contrast between the dignified, professional host, Alex Trebek (Will Ferrell), and his most frequent and infuriating contestant, Sean Connery (Darrell Hammond). Connery’s character quickly evolved from a mildly befuddled celebrity in the 1996 debut to an aggressive, crude, and consistently losing participant whose sole mission seemed to be the financial and emotional ruin of Trebek.
- Performer: Darrell Hammond
- First Appearance: December 7, 1996
- Signature Trait: Misreading category titles to create crude, sexual, or otherwise inappropriate phrases.
- Running Gag: Constant, personalized insults directed at Alex Trebek, often questioning his parentage or sexuality, and referring to him as "Trebek."
- Score: Almost always in the negative, often thousands of dollars below zero.
- Famous Line: "I'll take 'Anal Bum Cover' for $400."
- Relationship with Trebek: Arch-nemesis; a tormentor who delights in the host's suffering.
The character was so popular and well-executed that Darrell Hammond once claimed the real Sean Connery told him it was a better impression of him than he did of himself. The impression captured the Scottish actor's signature voice and gruff demeanor, twisting it into a vehicle for relentless, low-brow humor that never failed to land.
The 5 Most Outrageous Moments That Defined Connery's Reign of Terror
Sean Connery’s appearances were a masterclass in comedic escalation, with each sketch finding new, more absurd ways to torment poor Alex Trebek. The humor was derived from the sheer exhaustion of Trebek trying to maintain order against a constant barrage of ignorance and vulgarity.
1. The Infamous "Anal Bum Cover" Misreading
This is arguably the most famous moment in the entire run of Celebrity Jeopardy!. The category was "Potent Potables," a classic *Jeopardy!* category, but Connery was focused on the one below it. In one of the most iconic misreadings, he declared: "I'll take 'Anal Bum Cover' for $400." The intended category, of course, was "An Album Cover." The sheer audacity of the misreading, coupled with Trebek's immediate, defeated correction, set the gold standard for the sketch's humor. It perfectly encapsulates the character's crude mind and his total disregard for the rules or decency of the game show.
The running gag of misreading categories was Connery's bread and butter. Other memorable category misreads included "The Rapists" (The Therapists) and "Swords" (S. Words). The writers showed topical authority by consistently finding words that, when read with Connery's thick Scottish accent and crude mindset, transformed into something completely inappropriate.
2. The 'Catch These Men' and 'Le Tits Now' Debacle
In another classic moment, Connery selected the category "Catch These Men" for $800. The ensuing exchange, where the category was intended to be "Catch The Semen," is a prime example of the sketch's juvenile yet brilliant humor. The look of utter defeat on Will Ferrell's face as Alex Trebek, realizing the depths of Connery's mind, is priceless. This sketch also featured another classic misreading: "Le Tits Now," which was, in fact, "Let It Snow." The combination of French phrases and crude body parts was a specialty of the Connery character, highlighting the LSI keywords of misreadings and double entendres that the sketch thrived on.
These moments weren't just about the words; they were about the interaction. Connery's selection of the category was often accompanied by a suggestive leer or a dismissive wave towards Trebek, making the host's job impossible. The sketch expertly used the formal structure of *Jeopardy!* to amplify the absurdity of the celebrity contestants.
3. The Constant, Personalized Insults Towards Trebek
While the misreadings were the foundation of the sketch, the insults were the mortar that held the rivalry together. Connery’s insults towards Alex Trebek were relentless and specific, often revolving around Trebek's mother or his perceived lack of masculinity. "Your mother is a whore, Trebek," was a common refrain, delivered with Hammond's signature, gravelly Scottish brogue.
The insults were always unprovoked and completely irrelevant to the game, yet they were the core of the dynamic. Trebek, perpetually on the verge of a nervous breakdown, would try to maintain his composure, only for Connery to deliver a new, more savage zinger. This running gag established Connery not just as a poor player, but as Trebek's personal, malevolent force, a character entity that existed solely to cause the host pain.
4. The Turd Ferguson vs. Sean Connery Crossover
No discussion of Celebrity Jeopardy! is complete without mentioning the other great recurring character: Burt Reynolds, played by Norm MacDonald, who insisted on being referred to as "Turd Ferguson." The sketches where Connery and Reynolds appeared together were a comedic goldmine, as Trebek was forced to contend with two equally defiant and idiotic contestants. The dynamic between Connery's aggressive vulgarity and Reynolds' passive-aggressive insistence on his ridiculous nickname created a perfect storm of chaos.
In one of the final sketches, Reynolds even adopted Connery's habit of misreading categories, further pushing Trebek over the edge. The synergy between the two characters, both of whom were antithetical to the spirit of the game show, highlighted the sketch's satirical brilliance and its ability to build a cohesive, albeit insane, comedic universe.
5. The Final Jeopardy! Drawings and Wagers
The Final Jeopardy! round was always the moment of ultimate defeat for Alex Trebek. Since Connery's score was always deeply in the negative (often wagering and losing thousands of dollars he didn't have), his response was never a correct question. Instead, he would often draw a crude picture or write a nonsensical answer. In one sketch, Connery drew a picture of Will Ferrell's Alex Trebek urinating on his own grave, a shocking and hilarious act of final defiance that perfectly captured the character's nihilistic attitude toward the game and the host.
His wagers were equally absurd. Instead of a dollar amount, he would often write something like "Suck it, Trebek." These Final Jeopardy moments served as the climactic punchline, a final, definitive statement that the game was never about knowledge or money; it was simply about Connery winning the battle of wills against Trebek.
The Undying Legacy of a Classic SNL Sketch
The Celebrity Jeopardy! sketches, and specifically Darrell Hammond’s Sean Connery, are a testament to the power of character-driven comedy. They were a perfect blend of high-concept parody and low-brow humor, creating a recurring segment that is still quoted and watched today. The sketch has topical authority not only because of its humor but because it created an alternate reality for the beloved figures of Alex Trebek and Sean Connery.
The constant use of LSI keywords like "misread categories," "Turd Ferguson," "Will Ferrell Alex Trebek," and "Darrell Hammond Sean Connery" throughout the eleven-sketch run solidified its place as a comedy institution. The sketches are a brilliant example of how a simple premise—dumb celebrities on a game show—can be elevated to legendary status through exceptional writing and iconic performances.
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