Top 10 Funniest Celebrity Jeopardy Moments on SNL

The first “Celebrity Jeopardy!” sketch introduced staples like Will Ferrell as Alex Trebek and Darrell Hammond as Sean Connery. Their characterizations are slightly different with Trebek appearing more optimistic and Connery less antagonist. Norm Macdonald is also present as Burt Reynolds, but the most eccentric personality is Martin Short’s Jerry Lewis. Short captures Lewis at his most over-the-top, from the unhinged mannerisms to the obnoxious laugh. Lewis can’t stand still, even abandoning his podium during “Final Jeopardy!,” but he returns for one last zany bit. Funnily, Short previously appeared in a similar “SCTV” sketch called “Half-Wits,” which inspired Macdonald when conceiving “Celebrity Jeopardy!” Macdonald waited for Short to host to “ask permission to steal” from Eugene Levy, who wrote “Half-Wits.” He happily agreed.

Four years after Horatio Sanz brought Ozzy Osbourne to “Celebrity Jeopardy!,” Amy Poehler competed as the Prince of Darkness’ better half. She also brought her dog Minnie along for the occasion. Poehler’s enthusiasm as Osbourne perfectly contrasts Ferrell’s deadpan delivery as Trebek. One is full of life while the other is clearly dead inside. Despite Trebek urging her to select the “Automatic Points” category, Osbourne challenges herself with something more difficult. Well, difficult by “Celebrity Jeopardy!” contestant standards. When Sharon fails to tell the difference between three and seven, she responds the only way that an Osbourne can: with a tirade of bleeps. If you think that’s dirty, you should see what she wrote for “Final Jeopardy!” Actually, you can’t because it’s censored.

Jimmy Fallon popped up in six “Celebrity Jeopardy!” sketches, his French Stewart impression being one highlight. As Adam Sandler, Fallon became the first person to impersonate a former “SNL” cast member on the show. However, the unbearable weight of Fallon’s massive talent was most apparent in his Nicolas Cage impression. Fallon gets the Cage look down with untamable chest hair creeping out of his shirt collar. It’s the dramatic voice and mannerisms where Fallon shines the most, channeling Cage with such charisma that we wouldn’t be surprised if he took his face… off. Despite his incompetence, Fallon’s Cage comes out on top with an impressive $8. They’ll need that money to replace his podium, which was gone in 60 seconds. Okay, last Cage pun.

“Potent Potables” is frequently listed among the categories, although it wouldn’t be selected until the “40th Anniversary Special.” After being built up for almost 20 years, “Potent Potables” delivered a hilariously uncomfortable punchline. As part of the Video Daily Double, Kenan Thompson pops up as Bill Cosby, a role originally intended for Eddie Murphy until he turned it down. Cosby’s presence is awkward enough, but the fact that he’s making a cocktail takes the cringe to another level. Trebek quickly interrupts the video, saying that it was shot before Cosby’s descent into infamy. The damage is done, however. What’s worse, Trebek was the one who suggested “Potent Potables,” unintentionally setting himself up for humiliation. Trebek could use a drink after this… just not that one.

Two years before portraying Tom Cruise’s stunt double at the MTV Movie Awards, Ben Stiller channeled the man behind Ethan Hunt for “Celebrity Jeopardy!” Stiller could be mistaken for Cruise’s twin, from the way he raises his arms, to the perpetual grin of pearly whites, to the laugh that’s both infectious and kind of unsettling. Like the real Cruise, you’re never sure if Stiller’s caricature is going to hug you or snap at you. One second, he’s as cool as Joel Goodsen in “Risky Business.” The next, he’s as intense as Daniel Kaffee in “A Few Good Men.” Stiller goes for it and the results are uproarious. Cruise seems to take Stiller’s impression in stride, although Les Grossman might not be as forgiving.

“Celebrity Jeopardy!” could just as easily be called “Are You Smarter than a 5th Grader?” Then again, that wouldn’t be giving 5th graders enough credit, as even a preschooler would find these categories insultingly simple. Yet, whether it’s the alphabet, basic numbers, or noises that farm animals make, the most fundamental concepts elude these celebrities. Trebek tries to dumb down the categories as much as possible. Sometimes the category will be bizarrely specific like “Black Comedians Named Whoopi.” Other times, the answer will practically be in the title, such as, “What Color is Green.” Even when Trebek gift wraps points to the players with categories like “Don’t Do Anything,” they do everything wrong. We’ll take Famous Kareem Abdul-Jabbars for 400 points.

This sketch provides a platform for cast members and hosts to deliver their best celebrity impressions. If Tom Hanks proved anything with this surprise cameo, it’s that nobody does a better impression of himself than himself. Hanks appears genuinely oblivious as he speaks into his pen as if it’s a microphone, attempts to retrieve a pickle from a jar, and becomes trapped in a dry cleaning bag. In the vein of Forrest Gump, this version of Hanks isn’t the sharpest tool in the shed, but you can’t help but root for him. Of course, we think Forrest would be able to answer some of these questions correctly. Hanks is committed to the end, even if it leaves him with a bump on the head.

Will Ferrell ended his run as an “SNL” cast member in May 2002. His final show as a series regular included a very special “Celebrity Jeopardy!” In lieu of a “Final Jeopardy!,” the actual Alex Trebek walks on stage to join his mustached doppelganger. Even with the real deal present, Ferrell doesn’t break character. He maintains a stone face, but Ferrell is still evidently honored to be in the presence of the game show legend. It’s a bittersweet way to say goodbye that’s naturally interrupted by one of Connery’s insults. While Ferrell would return for more “Celebrity Jeopardy!,” this marked the only occasion that he shared the “SNL” stage with the late Trebek. Trebek himself “loved” Ferrell’s impression, second only to Eugene Levy’s.

Other than Hammond’s Connery, no contestant dropped by “Celebrity Jeopardy!” more times than Norm Macdonald’s version of Burt Reynolds. Oh, sorry, we mean, “​​Turd Ferguson.” Few could impersonate the “Cannonball Run” actor better than Macdonald, from the constant gum chewing to the way he answers every question with such misguided confidence. When he wasn’t misreading the category titles, Reynolds was tormenting Trebek with his oversized, foam cowboy hat. Some of our favorite appearances are the ones when Reynolds suddenly pops up as a contestant mid-game, much to Trebek’s confusion and annoyance. The last “Celebrity Jeopardy!” to date concludes with Reynolds shoving his hat on Trebek’s head. Whether or not “Celebrity Jeopardy!” ever returns in some capacity, this was a fitting farewell for Reynolds and Macdonald.

Before we unveil our top pick, here are a few honorable mentions.

With Great Power Kung-Fus Great Responsibility

A More Than Alright, Alright, Alright Cameo

Before Everyone on the Internet was Impersonating Goldblum

We’ll Drink to That

The Humor, The Humor

The Montagues and Capulets, Batman and the Joker, Trebek and Connery. As far as we know, there was no ill will between the real Connery and Trebek, but “SNL” turned their dynamic into one of the great rivalries. Where other contestants are dumber than 2x4s, Connery could probably win if he wanted. Yet, he’d rather troll Trebek by making obscene comments about his mother and misreading the categories in insanely inappropriate ways. While Trebek always remains civil, you can tell he’s screaming inside with every jab. Sometimes during “Final Jeopardy!,” it appears Connery may throw Trebek a bone with a genuine correct answer. He immediately erases any goodwill with his wager, saving the most savage insult for last. It’s just not “Celebrity Jeopardy!” without them.