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The Complete History of ‘SNL’s Celebrity Jeopardy

8. April 15, 2000

Sean Connery (Darrell Hammond)
Hillary 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 I guess you can get away with more as long as it’s in Sean Connery’s Scottish burr.

10. February 8, 2001

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

This sketch took place on one of SNL‘s Thursday Night Live specials and is another Jeopardy featuring all SNL cast members. Count on 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)
Chris Tucker (Dean Edwards)
Anne Heche (Reese Witherspoon)

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)
Dave Matthews (Jimmy Fallon)
Björk (Winona Ryder)

It should be mentioned that Trebek stoically endures all 14 sketches 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 has said that he loves 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 (who plays a pitch-perfect 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 impressionists.

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 in 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 that has lasted through all its staple characters leaving SNL, and now that Norm Macdonald has returned to television, I hope he hosts SNL soon and brings the Jeopardy gang back with him.

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/Christoph Waltz impressions, Jim Carrey and Alec Baldwin joined in, and even Kenan Thompson showed up as Bill Cosby in the Video Daily Double. Check out Norm Macdonald’s in-depth behind-the-scenes recap here.

Here’s to the next 15 “Celebrity Jeopardy” sketches!

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