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The Complete History of ‘SNL’s Celebrity Jeopardy

These days Norm Macdonald is all over the place — he has a Comedy Central special, a Twitter feud with Steve Martin, a profile in the New York Times, and a new show that premieres tonight. So what better time to revisit one of his most hilarious achievements ever: creating the original Saturday Night Live Celebrity Jeopardy sketch, which is one of the funniest and most enduring in the show’s history. Here they are from start to finish.

1. December 7, 1996

Norm Macdonald (Burt Reynolds)
Sean Connery (Darrell Hammond)
Jerry Lewis (Martin Short)

The first Celebrity Jeopardy sketch aired on December 7, 1996 with Will Ferrell as Alex Trebek, Norm Macdonald as Burt Reynolds, Darrell Hammond as Sean Connery, and host Martin Short as Jerry Lewis. The categories weren’t as absurdly juvenile as the later sketches (“Potent Potables,” “Movies,” “U.S. History,” “Popular Music”) and Hammond’s Sean Connery was cooperative and inoffensive. Norm Macdonald’s 70’s-era Burt Reynolds is the star here, and after all, Macdonald has admitted to creating the sketch simply to get his Reynolds impression on the show.

2. May 10, 1997

Burt Reynolds (Norm Macdonald)
Phil Donahue (Darrell Hammond)
Marlon Brando (John Goodman)


Unlike the first sketch, this one starts to integrate scoring and categories more into its humor. The contestants all start with negative scores, and even though the categories are still a bit dry (“Three Letter Words,” “Colors,” “U.S. States”), the contestants either ramble about unrelated topics or choose non-existent categories, so Trebek has to choose everything for them. This is also the only Celebrity Jeopardy sketch where the celebrities mention the charities they’re playing for — Reynolds plays for the Palm Beach Golf and Tennis Resort.

3. October 4, 1997

Burt Reynolds (Norm Macdonald)
John Travolta (Darrell Hammond)
Michael Keaton (Matthew Perry)

NBC executives fired Macdonald in early 1998 (see his hilarious post-firing Letterman interview here) and he was only in a few sketches for the remainder of the season, so the third Jeopardy sketch is the last time Macdonald plays Reynolds as an SNL cast member. Up until now, most of the categories have been pretty standard, but now they get notably stupider with “Words That Rhyme With Dog” and “Shapes,” and from this point forward the sketch brought us some great ones, like “Ponies,” “Foods That End In ‘Amburger,’” and “Black Comedians Named Whoopi.”

4. May 9, 1998

Sean Connery (Darrell Hammond)
Minnie Driver (Molly Shannon)
Jeff Goldblum (David Duchovny)

Now that Macdonald was no longer a cast member, Hammond reprised his role as Sean Connery and became the sketch’s staple character known for tormenting Trebek throughout each episode. In Live From New York: An Uncensored History of Saturday Night Live, Hammond says when he first did Sean Connery, “I had a really accurate Sean Connery. Now what I do is really a bastardization of who he is, because it just seems funnier to me and it’s funnier to the writers and it gets more of an audience response. Sometimes they just don’t want to see accuracy, they just want it to be funny.”

5. October 24, 1998

Sean Connery (Darrell Hammond)
Tom Cruise (Ben Stiller)
Adam Sandler (Jimmy Fallon)

By now the sketch found a consistent format: open at the start of the Double Jeopardy round with most of the celebrities’ scores low or in the negative. Already exhausted and annoyed, Trebek presents the categories to the celebrity contestants, which start with the standard “Potent Potables” then evolve into more childlike themes (“Colors That End In –Urple”). All questions clearly give away the answers (“This Number Comes Between Five and Seven,” “This Is The Sound A Doggy Makes”), but the contestants always fail to answer correctly and often fail to even choose a category. Connery turns at least one category into a sexual pun involving semen and/or having sex with Trebek’s mother, and eventually Trebek forces the game into the Final Jeopardy round. At least one of the contestants answers correctly but then makes an untranslatable wager, and Trebek ends the game with references to self-mutilation or suicide.

6. March 20, 1999

Sean Connery (Darrell Hammond)
Calista Flockhart (Drew Barrymore)
Nicolas Cage (Jimmy Fallon)

Jimmy Fallon impersonated a handful of stars in the Celebrity Jeopardy sketches including Adam Sandler, Hillary Swank, Robin Williams, and Nicolas Cage, and the sketch was the perfect opportunity for Fallon to show off his chameleon-like impersonation skills. He may have gotten flack on SNL for his corpsing (breaking character by laughing or making others laugh) habit, but Fallon thrives in sketches where he is allowed to either quickly change characters (like the radio DJ in his Z-105 sketches) or take one impersonation as far as possible (The Barry Gibb Show) — something that’s also served him well on Late Night.

7. October 23, 1999

Sean Connery (Darrell Hammond)
Burt Reynolds (Norm Macdonald)
French Stewart (Jimmy Fallon)

Only two years after he was fired, Macdonald was asked to return to SNL to host, so Burt Reynolds returned to Jeopardy with Connery and Jimmy Fallon as French Stewart. This is the sketch that gave birth to Turd Ferguson, one of comedy’s greatest names, and to see four strong SNL impressionists working together this well makes this one of the stand-out Jeopardy sketches.

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