The Complete History of SNL’s ‘Celebrity Jeopardy’

This article was originally published on April 12, 2011.

Norm Macdonald has been the star of many things over the years, including a recent stand-up special and upcoming Netflix talk show based on his hit web series/podcast Norm Macdonald Live. With his many accomplishments in mind, what better time to revisit one of his most hilarious achievements ever from his Saturday Night Live days: creating the original “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. Macdonald’s ‘70s-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. He’s also admitted to “stealing it, note for note,” from SCTV’s “Half Wits” sketch.

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, Hilary 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 flak 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 Talk Show”) — something that’s also served him well on Late Night and 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 impressionists 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 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)
Martha Stewart (Ana Gasteyer)
Ozzy Osbourne (Horatio Sanz)

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)
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 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 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/Christoph Waltz impressions, Jim Carrey and Alec Baldwin joined in, and even Kenan Thompson showed up as Bill Cosby in the Video Daily Double. Macdonald shared an in-depth behind-the-scenes recap of how this sketch came together on Twitter, which you can read in full below:

It was some week. I got in early, Monday, so I could write. It was a massive undertaking, a 3 hour show. People were exhausted. I worked with Lori Jo Hoekstra and Steve Higgins,who was always in a suit, because he had to go be Jimmy’s sidekick, every day, round 5. I saw Lorne, thanked him, congratulated him, and shook his hand as Canadians do. He accepted. Got that out of the way early. Mood was too relaxed. I was confused as to who exactly was to be in charge of this thing. It was to be Lorne Michaels. Of course. It was to be Lorne.

They wanted Celebrity Jeopardy. Higgins had two funny categories already figgered. I came up with the idea of Celebrity Jeopardy years ago by stealing it, note for note, from an SCTV classic, Half-Wits. Higgins and I co-wrote the first one years ago and I waited for Martin Short to host so I could ask permission to steal. He said that Eugene Levy had written the original. We received permission and beside Darrel and I, the talented Mr. Short played Jerry Lewis.

It was always difficult to fit in that final celebrity. We never wanted a celebrity to be dumb, although many, even within the show, thought that was the idea. The idea was for Connery to be abusive and Burt to be dismissive. Sometimes people ask me who the funnier character is, Connery or Burt. The funniest character in Celebrity Jeopardy, by far, is alex Trebek as played by Will. Without Will’s perfect take on Trebek, maddened by the outright hostility of Connery, the faraway uninterest of Burt, the sketch is nothing. Nothing but Rich Little nonsense. It was always the third podium that was hard to find a man to stand behind. It would inevitably only be an impression, nothing but an empty showcase. The best to do it was Hanks, playing dumb Hanks. Hanks always got it. And Alec too.

So we hunkered down to write it. 40th anniversary and all. Had to be the best one. Tough job. Very tough. Then I was told it was to have a lot of impressions, 10 or 12, so a lot of big stars could be seen impersonating other big stars. This was bad news. Celebrity Jeopardy was never about impressions. In real life, Connery is the opposite of Darryl’s take. Connery was the perfect gentleman, Burt was the funniest guy in the room. Celebrity Jeopardy was about hope. It was about the hope of one man, Alex Trebek, the hope that never died. The audacious hope that never let the facts of the past interfere. It was a rhythm piece, as each disaster was signaled by the sound of a buzzer, and each new category signified more, new, hope. And the 3rd contestant was the tough one. The third attitude always just out of reach of Higgins and me. And now we were being told we would have to do a dozen impressions. The rhythm would be gone. It was what it was, though, and what it was to be. How could it be saved from becoming an episode of copycats?

And then Higgins had an idea. An idea that would blow the show wide open. Among many other things, this show was to be the return of Eddie Murphy. Eddie, the man who, in Lorne’s absence, kept the show alive. Singlehandedly. To every comedian who ever performed on SNL, what Eddie accomplished was unthinkable. Every Saturday Night at 11:30 Eddie Murphy, a kid, would fill 90 minutes with comedy. Impossible. The last anniversary was the 25th. Eddie did not attend due to a remark by David Spade. David is a very kind man, but his remark was not. So Eddie never came back. Until last week.

Higgins had the idea. A video daily double. The category would be potent potables, a common one on Jeopardy, but one we somehow had never done. And the idea was that it would be a bar set. And the idea was that Cosby would be mixing a drink in a video that was taped 6 months ago. It was perfect. It was all Steve Higgins idea. At the end of the sketch, Darrel would choose potent potables. Homebase would be dressed as a bar. The iconic doors would open and on to home base would step Eddie Murphy. The audience would know what to do. Why is Eddie wearing a multi-colored sweater? He steps behind the bar, begins mixing a drink. The audience covers the fact he has not spoken. When he speaks, he is Cosby. Eddie Murphy doing a perfect Cosby impression. The audience does not let him finish. The sketch ends. The show, for all intents, ends. All the impressions are forgiven.

The first thing to do is cut down the number of contestant/impressions and the second is to contact Eddie and to convince him to do it. The middle man to talk to Eddie was @BrettRatner, a cool guy who knows a great deal about comedy. He was with Eddie somewhere. So, the talks were underway. “Brett says Eddie doesn’t feel comfortable”, “Eddie says ‘maybe it’s ok since he’s doing pre-allegation Cosby.” And on and on it went. I had not spoken to Eddie or @BrettRatner. I was dead sure Eddie would do it. Most others were not.

Still, there was so much work to do. Mike and Dana showed up. They were going to do Wayne’s World. I joined the writer’s room, which Mike helmed, and tried to help. Mike Myers has an incredible work ethic and no joke is ever good enough and must be beaten, must be beaten. This is what makes him so good. This is why he has created a half-dozen perfect comedies. Work ethic, remarkable taste, and never taking no for an answer. Higgins would stick his head in the room from time to time, tell me another celeb had been cut and make me happy. I kept trying to help Mike. I didn’t get a single joke into Wayne’s World. It was a great sketch, and he did a top ten list, best things about SNL. When, on air, he announced, “number 1, the crew”, the studio audience, unprompted gave a standing ovation. I’d never seen this in 8H.

Jim Downey, the best writer who ever touched pen to paper, showed up Wednesday, with a copy of Rolling Stone in his fist. The magazine had listed all 141 sat members and raked them, best to worst. “Guess where you ranked”, he laughed and I knew from the laugh it was low. “As long as I beat….” and I mentioned a girl who lasted 4 episodes. The joke was that I really hoped I would beat a girl who nobody had ever heard of. The bigger joke is that I hadn’t. My mind searched for an even more obscure cast member. I remembered the first year SNL hired an older man because they didn’t think all kids could play characters of age. “As long as I beat George Coe”, I said, making a fine joke. Again the truth was a finer joke. Coe had easily outranked me.” And on it went.

I should say that it was not the magazine that ranked us, but a single writer. I looked him up and found a book he had written. He doesn’t deserve to be named and his book was sentimental nonsense meant to look like something Dave Eggers would write. But, in all fairness, it was not the magazine who did the ranking. At least I think. Anyway, it made for a very funny running joke. The idea of jokes approved by a writer the caliber of Jim Downey being called lame by some sappy “writer” was a great joke. Downey was in charge of the political pieces, the best of which he had written, and nobody knew what was going on with Update. At least that’s what I was told the dozen or so times I was asked. Who was in charge of Update, i asked and eyes would get shifty. Was it the guy that wrote the Rolling Stone thing? Still, had to write Jeopardy. Higgins, Lori Jo, and I would stay late into the night, then go to PJ Clarks and end the nights at 3. It was like the old days. The old days. We worked straight through, me with my Winnipeg Jets jersey, Lori Jo in a beautiful dress, Higgins in his Tonight Show suit.

Downey had remembered a thing Bill Murray used to do around the office, the theme from Jaws, and thought that would be perfect. But there was a problem. Bill Murray was in Carmel for the Pro-Am, which he had won a couple of years back with DA Points. With Bill Murray, golf always comes first. And so it was Saturday and Bill Murray may not make it and Eddie Murphy may not do Jeopardy and who was in charge of Update? And chaos seemed ready to sink it all. So I went to Lorne. And Lorne was in his office, which overlooks 8H, which overlooks 40 years of memories. And he was looking out the window, down on to the floor. And I was very nervous and he was perfectly calm. “Perhaps it would help if you called Eddie”, and that was that.

My son got in on Saturday and wandered as the stars became bigger and bigger around him. I’m talking to Lori Jo and Higgins and Fred and my son and suddenly Paul McCartney is there. And he is in the circle of us and Lori Jo talks of being a vegan and he says his daughter works for Gucci and is a designer, but no leather. My son and I look at each other. Very cool. And the 4 of us follow McCartney in to 8H and he sits behind the piano and does 6 songs. I take a video on my phone of Fred Wolf, striking a Dylan pose, with McCartney in the background at the piano, singing. I get all filmmaker and go over Fred’s shoulder and get real close to Paul and when he finishes he is looking directly in to my camera. Then, as he finishes one and goes in to another I feel a hand on my back. The hand of security. Solid hand. There is Sarah Palin, gorgeous, and you can understand the charisma. She is irresistible. Too many superstars to take in all at one time. So happy my son could see them all.

And then comes Eddie. I’m standing with my son, Lori Jo, and Chris Rock. We see Eddie from 100 yards away. Rock says, “There he is. Like Ali in Zaire.” Eddie, Bomaye. It’s my job to talk him in to doing Jeopardy. We talk in his dressing room a good hour. When it’s over, I’m convinced he’ll do it. He doesn’t. He knew the laughs would bring the house down. Eddie Murphy knows what will work on SNL better than any one. Eddie decides the laughs are not worth it. He will not kick a man when he is down. Eddie Murphy, I realize, is not like the rest of us. Eddie does not need the laughs. Eddie Murphy is the coolest, a rockstar even in a room with actual rockstars. Quite a week.

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

The History of SNL’s Celebrity Jeopardy