Two of the biggest names in the history of entertainment, Sean Connery and Alex Trebek, tragically passed away eight days apart from each other in 2020. Of course, the two icons are forever immortalized by the body of work they left behind, but also in the long-running connection they share on the Saturday Night Live sketch, Celebrity Jeopardy.
Much of the appeal of the decades-long skit was seeing Sean Connery (Darrell Hammond) constantly roast Alex Trebek (Will Ferrell) through a series of hilarious insults, countered by Trebek’s disgusted reactions and retorts. In honor of both Connery and Trebek’s legacies, the best of the bunch can be found below.
10 Ozzy Osbourne, Martha Stewart & Sean Connery
One of the most hilarious Celebrity Jeopardy episodes includes Horatio Sanz as an overweight Ozzy Osbourne, Ana Gasteyer as the overly-pretentious Martha Stewart, and the reigning champion who makes every show better, Darrell Hammond as Sean Connery.
While Ozzy screams unintelligible words and Martha presents an winter cornucopia of figs and snow-tip eucalyptus, the show ramps up when Connery begins harassing Trebek with his trademark brand of inappropriately naughty humor. When Connery asks “Who is Craven Moorehead?” to one of the answers, Trebek responds by saying “Apparently,you are!”
9 Dave Matthews, Bjork & Sean Connery
In a rare Rock’n’Roll Celebrity episode, Jimmy Fallon plays musician Dave Matthews, Winona Ryder plays Icelandic singer Bjork, and Darrell Hammond plays the misfitting Sean Connery.
The skit features Matthews bringing out his band and singing his responses in his exaggerated singing voice, while Connery berates Trebek over his mother’s sexual indiscretions. However, Ryder steals the show as a loopy, nonsense-mumbling Bjork who speaks of making music by throwing nickels in the oven.
8 Sean Connery, Minnie Driver & Jeff Goldblum
One of the funniest aspects of Celebrity Jeopardy is watching various guest-hosts impersonate other movie stars. In this episode, David Duchovny does a hilarious imitation of spaced-out Jeff Goldblum, who is joined by a dimwitted Minnie Driver (Molly Shannon) and an insolent Sean Connery.
In keeping with a long-running motif in the skit’s history, Connery gives vulgar misreadings of the Jeopardy categories. Here, rather than choosing the category “Therapists,” Connery says “I’ll take The Rapists for 200.” Alex nearly faints as result.
7 Phil Donahue, Burt Reynolds & Marlon Brando
In one of the few times Hammond did not portray Sean Connery on Celebrity Jeopardy, he played famed talk-show host Phil Donahue. Joined by the air-headed Burt Reynolds (Norm McDonald) and the whacked-out Marlon Brando (John Goodman), this is one of the all-time best episodes not featuring Connery.
Goodman owns the episode playing Brando as a high-pitched mumbler slumped over his podium as he chews his fingernails and chooses categories that do not exist. As always, the gum-chewing Reynolds is so lost he can’t even answer his own birthday correctly.
6 Robin Williams, Catherine Zeta-Jones & Sean Connery
As Darrell Hammond became a mainstay as Sean Connery, Jimmy Fallon often appeared on Jeopardy as different celebrities. In one of his most memorable impressions, he played an ultra-hyper version of Robin Williams that paired perfectly with Connery and Lucy Liu as an exaggerated Catherine Zeta-Jones.
After a bearded and bespectacled Williams does a wild stand-up routine before the game even starts, Connery upstages him by saying disparaging remarks about Trebek’s mother. Connery then chooses the “an anal bum cover” category instead of “An Album Cover.”
5 Tom Cruise, Adam Sandler & Sean Connery
Ben Stiller as a zany Tom Cruise, Jimmy Fallon as a tremulous Adam Sandler, and Hammond as the ever-hilarious Sean Connery comprise one of the funniest panels on SNL’s Celebrity Jeopardy ever filmed.
In addition to the uproarious impersonations, the fifth iteration of the sketch features Connery spouting vulgarities as he mispronounces the “Famous Titles” category. After Sandler sings a song with his guitar, each contestant loses Final Jeopardy by failing to simply write down where they are.
4 Nicolas Cage, Calista Flockhart & Sean Connery
In the sixth edition of Celebrity Jeopardy, Sean Connery competes against the likes of hairy, gesticulating Nicolas Cage (Jimmy Fallon) and a vapid, whispering Calistsa Flockhart (Drew Barrymore).
Never missing a chance to humiliate Trebek, Connery opts for the “The Penis Mightier” category when it clearly states “The Pen Is Mightier.” As Trebek tries to save face and correct him, Connery doubles down by impugning Trebek’s manhood.
3 Sean Connery, Burt Reynolds & Jerry Lewis
The very first iteration of SNL’s Celebrity Jeopardy still ranks as one of the all-time funniest. In addition to introducing the two most hilarious recurring guests in Sean Connery (Hammond) and Burt Reynolds (McDonald), SNL alum Martin Short nearly stole the show with his impersonation of comedy legend Jerry Lewis. All four celebrities have since deceased.
The inaugural episode of the sketch set the tone and formula for years to come, with Connery memorably asking for “Swords” when the category reads “S Words,” a motif that would only become more vulgar as time went on.
2 Kathie Lee, Tom Hanks, Burt Reynolds & Sean Connery
In one of the most hysterical stints of the long-running sketch, Tom Hanks plays a dimwitted version of himself who is joined by Kathie Lee (Kristen Wiig), Burt Reynolds, and of course, Sean Connery.
The nearly ten-minute sketch features a rare four contestants, with Hanks making an absolute fool of his lovable public image. Meanwhile, Connery teases Trebek about having sex with his mother and Kathie Lee drinks her own zip-lock bag of white wine. When Reynolds shows up in his leather jacket and bolo tie, he begins hurling ignorant nonsense before vanishing into thin air.
1 French Stewart, Burt Reynolds & Sean Connery
The seventh edition of SNL’s Celebrity Jeopardy is the best of all. Trebek hosts a panel that includes French Stewart (Jimmy Fallon), Burt Reynolds, who insists on being called Turd Ferguson forevermore, and the ever-cheeky Sean Connery.
The sketch features some of the most memorable lines, best impressions, and induces the highest amount of laughter of all. Connery ribs and roasts Trebek about his mother’s sexual indiscretions, while Reynold pulls out a giant sombrero from backstage while continuing to spout utter nonsense. When Final Jeopardy asks the contestants to simply write down any number, Connery tricks Trebek by turning a roman numeral V into the K of the phrase “Suck it Trebek.”