It was 4:00 AM on a Tuesday. Darrell Hammond was staring at a blank page. He had absolutely nothing to turn in for the writers’ meeting. Desperation is a hell of a drug in the Saturday Night Live hallways, and it was in that pre-dawn fog that Hammond cooked up one of the most enduring, nonsensical rivalries in television history. He decided he was going to play Sean Connery as a relentless, vulgar bully. The target? Alex Trebek.
You’ve seen the clips. You know the voice. That gravelly, Scottish purr morphing into a weapon of psychological warfare. Sean Connery Celebrity Jeopardy SNL sketches shouldn't have worked. There was no real-life beef between the Bond actor and the game show host. Zero. Zilch. Yet, for over a decade, millions of viewers tuned in to watch a fictionalized version of Connery claim he spent the previous night with Trebek’s mother.
The Accidental Birth of an Icon
Hammond was actually nervous to pitch it. He didn't think the audience would buy it. Usually, satire needs a grain of truth—a real-life habit or a public scandal to lampoon. But Connery hating Trebek? It was pure fiction. Hammond told The Hollywood Reporter in 2020 that he thought the premise was "too arch." He worried people wouldn't laugh because they'd be too busy being confused.
He was wrong. Dead wrong.
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The magic was in the contrast. You had Will Ferrell’s Alex Trebek—a man who was essentially the human embodiment of a beige cardigan—trying to maintain order. Then you had Connery. He wasn't just there to play the game; he was there to dismantle Trebek’s soul. It was high-status meets low-brow. The Bond of all Bonds reduced to making "your mother" jokes while wearing a tuxedo.
The first sketch aired on December 7, 1996. It featured Martin Short as Jerry Lewis and Norm Macdonald as the legendary Burt Reynolds (later known as Turd Ferguson). But it was the Connery-Trebek dynamic that became the spine of the recurring bit. Out of the 15 total Celebrity Jeopardy! segments produced between 1996 and 2015, Hammond played Connery in 13 of them.
Why the categories were the real stars
A huge part of the Sean Connery Celebrity Jeopardy SNL legacy involves the deliberate misreading of the game board. It’s a simple gag, but the writers (including Norm Macdonald and Steve Higgins) turned it into an art form.
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- "Famous Titles" became "Famous Titties."
- "Therapists" became "The Rapists."
- "An Album Cover" became "Anal Bum Cover."
- "Let It Snow" became "Le Tits, Now." (A personal favorite of the late-night crowd).
It was juvenile. It was crude. Honestly, it was brilliant.
The Dynamics of the "Big Three"
While Connery was the primary antagonist, the sketches worked best when the "Big Three" were present: Ferrell’s Trebek, Hammond’s Connery, and Norm Macdonald’s Burt Reynolds. Macdonald’s Reynolds was a different kind of foil. He wasn't aggressive like Connery; he was just... there. He wanted a giant hat because it was "funny." He changed his name to Turd Ferguson because, well, it’s a funny name.
Connery, however, was a predator. He treated the lectern like a frontline trench. He’d offer a correct answer—a rare moment of competence—only to reveal a wager that said "Suck it, Trebek."
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The Real Alex Trebek’s Reaction
What did the real Alex Trebek think? He actually loved it. Trebek was famously a good sport, once noting that the parodies helped keep Jeopardy! in the cultural conversation. He even made a cameo in Ferrell’s final episode as a regular cast member in 2002. Seeing the real Trebek stand next to the fake Trebek while the fake Connery hurled insults was a meta-moment that few shows could pull off.
There's a subtle psychology to why we still watch these. Life is full of rigid rules and polite "game show" decorum. Seeing a legend like Connery (or at least Hammond’s hyper-masculine version of him) just absolutely refuse to play by those rules is cathartic. He didn't care about the money. He didn't care about the charity. He just wanted to win the "conundrum" he’d set for Trebek.
Key Moments You Might Have Forgotten
- The "S-Words" Incident: Connery insisted the category was "Swords" for $48,000. When Trebek corrected him, Connery’s disappointment was visible.
- The Handwriting: Connery once claimed he wrote Trebek’s name in a snowbank. "Of course, it was your mother's handwriting! She was holding the pen!"
- The 40th Anniversary: Even in 2015, years after the original run, the bit killed. When Connery mistook "Who Reads" for "Whore Ads," it felt like no time had passed at all.
How to Watch Them Today
If you’re looking to fall down the rabbit hole, NBC and the official SNL YouTube channel have archived most of these. They aren't just nostalgia; they are a masterclass in "straight man" comedy. Will Ferrell’s slow descent into madness is just as funny as Hammond’s absurd Scottish accent.
Next Steps for the Superfan:
- Watch the "Rock & Roll" Edition (2002): This is the one where Trebek makes his cameo and Connery records an album of "filthy limericks" just to be eligible for the show.
- Listen to Darrell Hammond’s Interviews: He’s spoken extensively on various podcasts about the technical side of the voice—how he had to find a way to make it sound like Connery while keeping the "mean" energy high.
- Check out the Turd Ferguson origins: To get the full context of the rivalry, you have to see Norm Macdonald’s introduction of the oversized foam hat.
The Sean Connery Celebrity Jeopardy SNL sketches remain a pinnacle of late-night TV because they didn't try to be "important." They were just funny. In a world of over-analyzed media, sometimes you just need a man in a fake beard telling a game show host to "shuck it."