With the passing of Sean Connery and Alex Trebek within a week of each other, I bet you never really saw a connection between these two.

And you’d be right. As far as I can tell, they never even met before. But they were forever tied together by an SNL sketch popular in the nineties: Celebrity Jeopardy. This was in my mind the last decade that Saturday Night Live was funny.

Saturday Night Live started in 1975 with the not ready for primetime players that most people feel was the funniest the show ever was. But there were some very funny casts over the decades. After the originals, there was the Eddie Murphy Billy Crystal year. Then a new group was brought in that included greats like Phil Hartman, Mike Meyers, Adam Sandler, Chris Farley, and Chris Rock.

Once those guys drifted off, SNL redid their cast again adding in Will Ferrell, Chris Kattan, Cheri Oteri, Molly Shannon, Jimmy Fallon, and Darrel Hammond.

It was Ferrell and Hammond who started Celebrity Jeopardy. This is probably in the top five of all time funniest sketches of all time. Maybe the best. Many of the sketches in 70’s don’t exactly hold up. Two Wild And Crazy Guys and Coneheads is like fingernails on chalkboards to me at this point.

But Celebrity Jeopardy is only marred by the fact a few of the “celebrities” they spoofed aren’t really relevant as they were. But only a few.

I recall clearly before the actual sketches coming out that the real “Celebrity Jeopardy!” was quite a bit dumbed down from the actual show. Even as a teenager, I was able to answer nearly all the questions correctly. They weren’t completely dumb but the level of difficulty was clearly not Jeopardy’s normal setting of “Nightmare”.

It was created originally by Norm MacDonald who apparently noticed the same thing. He also had to run it by Eugene Levy who had done a game show parody on SCTV called “Half Wits.” Eugene gave his blessing and off it went. Reportedly, the real reason he wanted to do it was so MacDonald could do his Burt Reynolds impression.

The first one ran on December 7, 1996 and had Hammond as Connery, MacDonald as Reynolds, and guest host Martin Short as Jerry Lewis.

This was also the first time they used the trope of mistaking the category name for a different word, but it wouldn’t become awesome until a bit later. Overall a good first start.

The genius of this is the arrogance and stupidity on display. Watching celebrities bleat on today about things they know nothing about has aged like fine wine.

The next two also had MacDonald as Burt Reynolds with Hammond trying out a couple of more impressions and guest hosts playing various other celeb. John Goodman as Marlon Brando is particularly good.

However it was the next one that really cemented Hammond’s Connery as a mainstay with his surly attitude towards Trebek and laugh out loud moment when he picked the category “Therapists.”

At this point they had gold. It continued being a mainstay during Ferrell’s run on the show. It’s one of the few characters Ferrell ever played straight. Connery continued to get more and more antagonistic towards poor Trebek who is the only one attempting to take the game seriously.

The last one with Ferrell still as a regular cast member included a nice cameo with the real Alex Trebek.

While its unknown how Connery felt about it or if he even was aware of it, Trebek loved it. In a nice bit of symmetry, many of these categories ended up on the real Jeopardy. One of the contestants even yelled “Surprise Me, Trebek!” in a Connery impression.

It came back around a few more times in later years when Ferrell hosted. The best is when Tom Hanks appeared as… Tom Hanks.

The last one was during the SNL 40th Anniversary special and featured all kinds of people coming in and out. It still showed that this sketch works even nearly twenty years later.

Now with Connery and Trebek having passed away, this will probably never come back. But we’ll always have the ones they did create. Anything that takes down celebrities is good with me. It was a great way to show how ego, arrogance, and ignorance can mix together to hilarious results.

Reading any random celeb’s twitter these days makes you realize why this sketch hit home.