Saturday Night Live had a banner year last season, with strong ratings, a cast filled with household names, and edgy humor that went viral across the nation. But let’s not forget the last SNL golden age, when actors like Will Ferrell and Norm Macdonald roamed the stage.
One of the most memorable sketches from that era starred Ferrell as embattled game show host Alex Trebek and Darrell Hammond as a very intellectually dull yet volatile Sean Connery on the set of Celebrity Jeopardy. The sketches, which aired between 1996 and 2009 (with a special reprise in 2015 for the show’s 40th anniversary episode), capture something magical, and a lot of it has to do with the Connery character played by Hammond, who without question steals the show.
We’ve collected eight of the best Celebrity Jeopardy “Sean Connery” moments, starting with his first appearance and ending with his last.
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Swords (Season 22, 1996)
Ah, here it is — the very first Celebrity Jeopardy skit from 1996. So many themes that we will enjoy for the next 14 years are captured here: super-easy questions, easily distracted guests, a very annoyed “Trebek” and of course, mispronounced category titles. There is perhaps no greater moment than the one when Hammond’s Sean Connery reads the category “‘S’ Words” as “Swords,” starting a sketch tradition that would last for over a decade.
Also notable in this episode: Norm Macdonald plays Burt Reynolds for the first time in this series of sketches, while Martin Short plays the iconic Jerry Lewis.
Your mother (Season 23, 1998)
For some reason, Hammond’s Connery character is very crude, especially when it comes to the topic of “Trebek’s” mother. It’s never more apparent than in this 1998 episode, when the Connery character attempts to answer a very, very easy question: “What sound does a doggy make?” “Connery” buzzes in to answer, “Moo.” When he is told he’s wrong, he says in a matter-of-fact manner, “Well, that’s the sound your mother makes.”
We know it’s childish, but it’s still wonderfully funny.
Also notable in this episode: This is the first time that “Burt Reynolds” refers to himself as Turd Ferguson, a running gag that is also very childish but that we still think is funny for some reason.
Are horsies pretty? (Season 24, 1999)
A year later, Celebrity Jeopardy returned, this time with Hammond’s Connery playing against “Calista Flockhart” (as played by Drew Barrymore) and “Nicolas Cage” (Jimmy Fallon). The trio struggles think of “Months That Begin With Feb,” such as “Febtober,” and the Sean Connery character misreads the category “The Pen Is Mightier” as “The Penis Mightier.”
Also notable in this episode: This episode has some of the funniest dumbed-down categories in it, including “Shiny Objects,” “Things You Shouldn’t Put In Your Mouth” and finally, “Horsies” for Final Jeopardy. No one could answer the question, “Are horsies pretty?”
My day has come! (Season 25, 2000)
For this episode, “Hilary Swank” (one of Fallon’s impressions) and “Keanu Reeves” (played by host Tobey Maguire) join Hammond’s Connery in one of the dumbest and most disruptive games of Celebrity Jeopardy yet. The contests struggle mightily to figure out a color that ends in “urple,” while “Connery” laughs, “My day has come!” when the Final Jeopardy answer is “Famous Mothers.”
Also notable in this episode: Even though Hammond’s Sean Connery impression is as delightful as ever in this episode, we have to admit that Tobey Maguire’s Keanu Reeves impression is the best thing we have ever seen. We actually want Maguire playing Reeves to act in Keanu Reeves’ next movie.
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What is Robin? (Season 27, 2001)
Contestants “Chris Tucker” (Dean Edwards) and “Anne Heche” (Reese Witherspoon) attempt to beat SNL‘s Connery character at Celebrity Jeopardy while “Connery” spends much of his time antagonizing Ferrell’s Alex Trebek.
The best moment of this sketch is when the trio are shown a picture that is obviously Batman and asked “Batman or Robin?” and the answers are amazing:
“Chris Tucker”: Robin?
“Anne Heche”: Who is Robin?
“Sean Connery”: What is Robin?
While this is going on, “Trebek” tries and fails to keep his composure.
Also notable in this episode: As usual, the contestants begin with all negative numbers for the charities they are playing for. Of all of the Celebrity Jeopardy sketches, the most any player ever makes is $14 (and yep, it’s “Burt Reynolds”).
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40th anniversary special: “Le Tits Now”
Just when we thought it was gone forever, especially when Hammond left the show, Celebrity Jeopardy returned for the 40th anniversary show in 2015. Kate McKinnon brilliantly plays Justin Bieber, while Alec Baldwin plays Tony Bennett. Later in the sketch, Jim Carrey plays Matthew McConaughey and Norm Macdonald’s Burt Reynolds returns one last time.
Hammond’s Connery character shows up in full force, misreading the category “Who Reads?” as “Whore Ads” and misreading “Let it Snow” as “Le Tits Now.”
Also notable in this episode: Our personal favorite joke in this sketch that isn’t related to Hammond’s hilarious Sean Connery impression is when McKinnon’s Bieber can’t seem to stop calling Ferrell’s Trebek, “girl.”
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