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The Complete History of SNL’s ‘Celebrity Jeopardy’

This article was originally published on April 12, 2011. It has been updated.

Few recurring Saturday Night Live sketches have achieved the immortal status of “Celebrity Jeopardy.” For nearly 20 years, the sketch — which has aired a total of 15 installments — served as one of the NBC series’s most hilarious showcases for very silly impersonations, including Winona Ryder as Björk, Ben Stiller as Tom Cruise, and Tom Hanks as a very dumb version of Tom Hanks. But the heart of the sketch has always been the three celebrities who appeared most often: Will Ferrell playing the eternally exhausted Jeopardy! host Alex Trebek, Norm Macdonald as the careless and funny hat-wearing Burt Reynolds, and Darrell Hammond as Sean Connery, who always managed to fit in at least one joke about having sex with Trebek’s mother. “It’s third-grade humor, which is the best kind of humor,” writer-producer Steve Higgins explained to Variety after the death of the real Trebek in November 2020. “People would talk about the sketch and say that the celebrities were dumb. But that wasn’t it. It was that they didn’t care. They just wanted to burn Alex Trebek. And why? Because he’s so unassailably good.”

There are two stories about the origins of “Celebrity Jeopardy.” The first is from Higgins, who in his 2020 talk with Variety credited his wife for coming up with the initial concept for the sketch in 1996, which led to him co-writing the first installment with Adam McKay. The other comes from Norm Macdonald, who said in his 2015 recap of SNL’s 40th anniversary special that he got the idea for the sketch “by stealing it, note for note, from an SCTV classic, ‘Half-Wits’” after asking Martin Short and Eugene Levy for permission. The definitive origin of the sketch remains unclear, but like the “Celebrity Jeopardy” sketch itself, it’s not easy to find the correct answer.

Thanks to the impersonation skills of the SNL cast — plus some comedy-writing talent from Higgins, Macdonald, McKay, Mike Schur, Robert Carlock, Erik Kenward, and Seth Meyers over the years — “Celebrity Jeopardy” quickly evolved from a silly one-off sketch to a recurring favorite. “I’m just lucky that I got to be a part of it,” Higgins told Variety. “That’s the best thing I’ve ever done.”

Here, for your viewing pleasure, is the complete collection of every “Celebrity Jeopardy” sketch, 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. Macdonald’s ’70s-era Burt Reynolds is the star here.

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 was the last time Macdonald played 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 explained that 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, Hilary Swank, Robin Williams, and Nicolas Cage, and the sketch was the perfect opportunity for him to show off his chameleon-like impersonation skills. He may have gotten flak on SNL for his his habit of constantly breaking, but Fallon thrived in sketches where he was 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 Talk Show”) — something that also served him well on Late Night and, later, The Tonight Show.

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 impersonators working together this well makes this one of the stand-out “Jeopardy” sketches.

8. April 15, 2000

Sean Connery (Darrell Hammond)
Hilary Swank (Jimmy Fallon)
Keanu Reeves (Tobey Maguire)

Most hosts hadn’t been SNL cast members, but that didn’t stop some of them from stealing the spotlight. Tobey Macguire’s Keanu Reeves is adorable here, David Duchovny does a great Jeff Goldblum, and Winona Ryder takes the cake for me with her creepy spot-on Björk impression (“When I look at the veins in my hands, they remind me of these two snakes that laugh.”). A good SNL host is one thing, but a good SNL host who can do a celebrity impression and hold their ground against the “Jeopardy” regulars is pretty impressive.

9. December 16, 2000

Sean Connery (Darrell Hammond)
Robin Williams (Jimmy Fallon)
Catherine Zeta-Jones (Lucy Liu)

Another great part of these sketches is when Connery purposely confuses a category with something offensive. In this case, “An Album Cover” becomes “Anal Bum Cover,” but there are plenty others. And now that they’re all grouped together, it’s surprising to know this level of humor made it to air, but maybe it’s easier to get away with as long as it’s in Sean Connery’s Scottish burr.

10. February 8, 2001

Sean Connery (Darrell Hammond)
Martha Stewart (Ana Gasteyer)
Ozzy Osbourne (Horatio Sanz)

This sketch aired during one of SNL’s Thursday Night Live specials and is another “Jeopardy” featuring all SNL cast members. Count on Hammond’s Connery to turn the category “Richard Nixon” into “Hard On” and drive Trebek to keep a flask in his pocket ready for times he wants to kill Connery for his mental torture.

11. September 29, 2001

Sean Connery (Darrell Hammond)
Anne Heche (Reese Witherspoon)
Chris Tucker (Dean Edwards)

Will Ferrell has referred to the “Jeopardy” sketch as “the spirit of Saturday Night Live,” and he couldn’t be more right, especially for this sketch, which took place during the first SNL episode after the September 11th attacks. Reese Witherspoon’s commitment to her duty as host was commendable, and SNL showed us that it was okay to laugh again, particularly when Connery vandalizes the “Famous Horsemen” category so it reads “Hore Semen.”

12. May 18, 2002

Sean Connery (Darrell Hammond)
Björk (Winona Ryder)
Dave Matthews (Jimmy Fallon)

It should be mentioned that Trebek stoically endures every “Jeopardy” sketch drowning in hopeless disbelief for the celebrity stupidity around him, so for Ferrell’s last episode as an SNL cast member, the real Alex Trebek made a cameo. Trebek said that he loved SNL’s “Jeopardy” sketches and was “extremely disappointed when Will left. We’ve never had any contestants as ornery as the Sean Connery character that Darrell Hammond portrays. I’ve been asked how I would feel if we had Sean Connery on Celebrity Jeopardy! I tell everyone I’d just walk up to him and punch out his lights.”

13. May 14, 2005

Sean Connery (Darrell Hammond)
Bill Cosby (Kenan Thompson)
Sharon Osbourne (Amy Poehler)

Will Ferrell came back to host SNL in 2005, and “Jeopardy” first-timers Amy Poehler (as Sharon Osbourne) and Kenan Thompson (as Bill Cosby) joined Ferrell and Hammond to bring back the sketch after a three-year absence. The timelessness of the sketch has made it immune to danger from breaks, current events, and cast switch-ups; all that’s needed for it to survive is Trebek, Connery, and two more talented impersonators.

14. May 16, 2009

Burt Reynolds (Norm Macdonald)
Sean Connery (Darrell Hammond)
Tom Hanks (Tom Hanks)
Kathie Lee Gifford (Kristen Wiig)

Will Ferrell returned again to host in 2009 for Darrell Hammond’s last episode as a cast member after a record-breaking 14-year run at SNL. Now that the last original “Celebrity Jeopardy” cast member was leaving the show, it was only appropriate for Norm Macdonald to return as Reynolds as well, and the three originals got plenty of hilarious support from Kristen Wiig as drunk Kathie Lee Gifford and Tom Hanks playing super-stupid Tom Hanks. It’s nice to see this sketch gain an immortal status here that lasted beyond all of its staple characters leaving SNL.

15. February 15, 2015

Burt Reynolds (Norm Macdonald)
Sean Connery (Darrell Hammond)
Justin Bieber (Kate McKinnon)
Christoph Waltz (Taran Killam)
Tony Bennett (Alec Baldwin)
Matthew McConaughey (Jim Carrey)
Bill Cosby (Kenan Thompson)

SNL’s 40th anniversary special brought “Celebrity Jeopardy” out of its six-year absence in high style packed with stars: Sean Connery and Turd Ferguson returned, “Jeopardy” newbies Kate McKinnon and Taran Killam got to show off their perfect Justin Bieber and Christoph Waltz impersonations, Jim Carrey and Alec Baldwin joined in, and even Kenan Thompson showed up as Bill Cosby in the Video Daily Double. Afterwards, Macdonald shared an in-depth behind-the-scenes recap of how this sketch came together on Twitter, which you can read in full here.

While “Celebrity Jeopardy” hasn’t returned to SNL since the 40th anniversary special, the show responded to the news of Alex Trebek’s death in 2020 the best way they could: by sharing a clip on November 9 of the Jeopardy! host’s cameo from 2002, adding, “Thank you, Alex.” Norm Macdonald reacted to the Trebek news on Twitter the same day by revealing that he had written a “Celebrity Jeopardy” sketch after the game-show host revealed his cancer diagnosis in 2019, but SNL turned the idea down. Darrell Hammond also responded to the Trebek news on Twitter, writing, “RIP to a wonderful person and an absolute class act. He will definitely be missed.”

Sean Connery died just a week before Trebek, and Burt Reynolds passed away two years earlier in September 2018. The main players who inspired the spirit of the sketch might be gone, but one thing is certain: “Celebrity Jeopardy” lives on as an SNL classic forever. Or, as Macdonald put it in 2015, “‘Celebrity Jeopardy’ was about hope. It was about the hope of one man, Alex Trebek, the hope that never died.”

Here’s to the next 15 sketches.