Alex Trebek's best guest appearances

Alex Trebek is one of the most famous people in the world, his face and name instantly and delightedly recognizable by almost anyone. That's bound to happen to a guy who appears on television five days a week for more than 35 years. While he's hosted other game shows before and since, Trebek is synonymous with Jeopardy!, the show that made his gently authoritative demeanor and crisp tone universally known. 

While he must enjoy hosting Jeopardy! (he's kept more than 7,000 episodes going and flowing, after all), Trebek seems to really like being a TV personality, and spreading fun and good cheer. The host has appeared on dozens of TV shows, usually playing himself (or a heightened version of himself). He's also not afraid to poke a little fun at his image, career, or his sometimes sternly-approached Jeopardy! duties. Here are some times when Alex Trebek moonlighted on a non-game show... and stole the show in the process.

The truth about Trebek is out there

"Jose Chung's From Outer Space," a 1996 episode of The X-Files, builds up the show's vast alien coverup conspiracy, but with a touch of humor for once. And it features not one but two celebrity cameos, disparate as they are. FBI investigator Fox Mulder (David Duchovny) speaks with one of the fabled "men in black," and tells him how hard it is for anyone to ever discuss a meeting with someone in this conspiracy network without coming off as "a lunatic." 

The man in black (portrayed by a post-wrestling, pre-governor of Minnesota Jesse Ventura) dismisses Mulder's concerns, only for a second Man in Black to lay a hand on his shoulder. "You're feeling very sleepy. Very... relaxed," the man ominously intones in a not-quite-recognizable accent. He's partially shroud in darkness and his face is obscured by a giant Stetson hat, but the guy is clearly Alex Trebek. Or is he? The scene cuts to the present day, where Mulder's partner, Dana Scully (Gillian Anderson) explains the previous sequence to an author (Charles Nelson Reilly), clarifying that Mulder didn't say the Man in Black was Alex Trebek, but merely "someone that looked incredibly like him."

The ol' Alex Trebek shakedown

Alex Trebek voiced an animated version of himself on The Simpsons three times. On the first occasion, he pulled back the curtain on the shocking truth behind a Jeopardy! trope — just what happens when a contestant finishes the game with a negative dollar amount. In the 1997 episode "Miracle on Evergreen Terrace," Bart wakes up early on Christmas morning to play with his toys, including a remote-controlled fire truck that he crashes into the Christmas tree, and, ironically, sets the entire holiday haul on fire, hiding the evidence and concocting a story about a robbery. 

The story makes the news, and the town donates more than $10,000 before Bart's lie is revealed. The family become pariahs, so Marge, aiming to earn enough money to pay everybody back, does the reasonable and realistic thing and competes as a contestant on Jeopardy! She fails miserably, and as she tries to leave the TV studio, she's stopped by Trebek. "Aren't we forgetting something, Marge?" he asks. "You were down $5,200." He wants that money, and he wants it now. "Judges!" Trebek calls out with a snap of his fingers, summoning his official game show "muscle."

Cheers to you, Trebek

Jeopardy! contestants judge their performance on a spectrum. They aim to do so well that they wind up with the likes of unstoppable champions Ken Jennings and James Holzhauer... and they hope to avoid repeating the fate that befell Cliff Clavin. He's Cheers' fictional mailman portrayed by John Ratzenberger, who attempts to put his vast knowledge of trivia and annoying fun facts to use with an appearance on Jeopardy! in the memorable 1990 episode, "What is... Cliff Clavin?" To wit: he racks up $22,000 going into "Final Jeopardy," but blows it all by responding to a clue about the real names of a trio of movie stars with the utterly ridiculous "Who are three people who've never been in my kitchen?"

Alex Trebek appears as himself, hosting this not-real episode of Jeopardy! He's fully in "character," too, responding with his characteristic combination of restraint, patience, and light teasing when dealing with the socially awkward Cliff. But this particular contestant really tests Trebek, especially when the host has to call him out on trying to cheat by looking over his partition to see what another contestant wrote down for her "Final Jeopardy" response. After Cliff loses the game, Trebek can't believe the idiocy in action and cries out at the hapless postman, "Why did you do something like that?"

It's Double Jeopardy

Of Will Ferrell's many famous sketches and characters in his tenure at Saturday Night Live, perhaps none were more popular than "Celebrity Jeopardy!" and his portrayal of host Alex Trebek. Ferrell didn't really imitate Trebek's voice, but played him as an always-put-upon and frustrated guy who just wanted to keep his game show moving. Of course, he was constantly thwarted by the celebrity contestants' incredibly stupid and nonsensical responses, not to mention the profane hostility of Sean Connery (Darrell Hammond). 

SNL put on a "Celebrity Jeopardy!" for Ferrell's last show as a cast member in 2002. As Ferrell-as-Trebek tries to segue into "Final Jeopardy," the real Trebek emerges from the wings. "And so this was your final Jeopardy!" he says, before comforting the fictional version of himself. "Those celebrities did not know the right answer to any of your questions!" real Trebek points out to fake Trebek. "No, they did not," Ferrell's character replies. "They were very stupid." 

It was then the real Trebek who finally got to talk back to this sketch's cruel Connery. After he delivers a homophobic slur, Trebek snaps, "Back off, Connery. I don't have to take that from you." He can only look on, however, as the former James Bond gets the last word: "I guess it's true, old married couples do start to look alike." Ferrell remains in character for the whole exchange, giving viewers a world in which two Alex Trebeks co-exist.

Back to the fifth dimension where he belongs

Alex Trebek's day-to-day work life seems fairly reliable: go to the Jeopardy! studio, read clues off of board, tell contestants if they got them right or wrong, declare a winner, and go home. His experience on Family Guy represents a wild break from the ordinary — voicing himself on a strictly adults-only cartoon — while also imagining a bizarre break with reality. 

On the 2006 Family Guy episode "I Take Thee, Quagmire," Brian the talking dog recalls the "strangest thing" he "ever saw on a game show." In one of Family Guy's signature cutaway gags, Mayor Adam West appears as a contestant on Jeopardy! Trebek asks to see West's response to the "Final Jeopardy" clue about the first spacecraft to land on Mars. West's podium shows that he wrote "Kebert Xela." Trebek reads those seemingly nonsense words aloud. A look of panic crosses the cartoon Trebek's face, and he screams as he transforms into a beam of orange and yellow light. Mayor West flatly explains, "Only saying his name backwards can send him back to the Fifth Dimension, where he belongs."

Parks and Trebek-reation

Hot in Cleveland, TV Land's pleasant throwback to old-fashioned, shot-in-front-of-a-live-studio-audience sitcoms, opened its fifth season in 2014 with "Stayin' Alive," a live-to-air episode. That meant pulling out all the stops to make a newsworthy spectacular. The plot alone was uncharacteristically wacky, with special guest star Ken Jeong playing a plastic surgeon obsessed with Wendie Malick's character. Meanwhile, the show's main cast is trapped in a cabin in the woods that some bank robbers are using as a hideout. Alex Trebek appears at the beginning of the episode to deliver an introduction. But there's plenty more where that came from. 

After the party sends out a distress call in the form of smoke signals, a gun-toting Trebek suddenly darkens the cabin's doorway. He orders the criminals to throw down their guns, and crisis is averted. This is one of the few times Trebek has appeared on TV not wearing a suit, but rather the khaki uniform of a park ranger. "Alex Trebek?" shouts character Melanie (Valerie Bertinelli). "That's right," he says. "But on weekends I'm Park Ranger Alex Trebek." He explains that he received their S.O.S. "I read your smoke signals telling me that there were women here in...," he starts before turning to the camera to quip, "jeopardy." And then he winks at the camera.

What a know-it-all

"Weird Al" Yankovic has a couple of Jeopardy! connections. In 1984, he recorded a parody of the Greg Kihn Band's "Jeopardy" with "I Lost on Jeopardy," a song from the point of view of a guy who pulls a Cliff Clavin on Jeopardy! In 1997, Yankovic returned to the JepVerse with a segment on his Saturday morning sketch comedy/sitcom hybrid The Weird Al Show. While Yankovic channel surfs, he comes across a commercial for a correspondence school. These kinds of ads ran all the time in the '90s, offering people the chance to learn a trade like TV/VCR repair or bookkeeping from the comfort of their home. But in the surreal world of "Weird Al," the pitch-person for this correspondence school is TV's Alex Trebek. 

"Would you like to make more money? Impress your friends?" Trebek asks. "Be like me and know everything in the world?" That can happen, he promises, with some classes from the Know-It-All Correspondence School. Trebek goes for the hard sell, keeping a straight face as he earnestly implores the skill-less to learn extraordinarily wacky skills including "Molecular Biology," "Aardvark Training," "Bellybutton Lint Recycling," "Frog Cosmetology," and, uh, "Accounting."

Orange is the new Trebek

Inmate Suzanne "Crazy Eyes" Warren struggled mightily with mental illness throughout the run of Orange is the New Black. The sixth season of the series kicks off with the character alone in her jail cell, talking to herself and hallucinating that she's flipping through TV channels. Each of the unsettling "shows" features an Orange is the New Black inmate, including Nicky (Natasha Lyonne) as Rowlf from The Muppet Show and Frida (Dale Soules) as a magician performing card tricks. 

Then she discovers a dark version of Jeopardy! Suzanne conjures up Alex Trebek, who stands in front of a Jeopardy! logo and reads off a series of clues, all of which are frantically answered "Where is Alex?" by inmate Piper (Taylor Schilling) standing behind a Jeopardy! contestant podium. She's likely referring to her girlfriend, an inmate named Alex, but after the third and final "Where's Alex?" the other Alex — as in Trebek — replies, "Here, b****." Who would have thought back in 1984, when Alex Trebek started hosting Jeopardy!, that he'd one day make fun of himself — and swear — on a TV show about a women's prison?

Hey, it's Alan Quebec!

When the script for a narrative TV program — a kid's cartoon series, for example — calls for a character to appear on a game show, it makes sense to bring in a real-life game show host for those scenes. That cameo is a fun way to add realism. Jeopardy! host Alex Trebek seems to be ready and willing to moonlight not just as himself, but as the host of other, fictional game shows.

The 1993 Rugrats episode "Game Show Didi" is the rare installment focused primarily not on the show's titular babies, but on the babies' parents. Didi Pickles lands a spot on the prestigious TV quiz show Super Stumpers, and spends days trying to cram like it's a school exam. She's pitted against a tough-to-beat genius on the game show, an obvious parody of Jeopardy! As if the reference wasn't clear enough, it's buoyed by the guy who plays the Super Stumpers host: Trebek. However, he doesn't play "Alex Trebek" but rather the similarly named "Alan Quebec," which is perhaps a subtle nod to Trebek's Canadian heritage.

Alex Trebek as the Riddler

Seven years after his first gig as the fictional host of a make-believe game show on a children's animated TV series, Trebek once again lightly sent up his image in the 2000 Arthur episode "Arthur and the Big Riddle." Trebek is a cartoon again, although this time he's an anthropomorphized aardvark (like Arthur Read and his family), and he's the host of a popular game show called Riddle Quest. 

A mix of Jeopardy! and Double Dare but with riddles, the game features two kids answering tricky, tough-to-solve brainteasers to earn fabulous prizes. Arthur's best friend Buster thinks he'd be an ideal contestant, and volunteers him by mailing a letter to Riddle Quest's studio. Arthur, of course, makes it onto the show when the aloof host (and most powerful producer, apparently) "Alex Lebek" (voiced by Trebek, of course) picks Buster's letter at random out of a mailbag while getting his very important game show host hair cut.

Alex Trebek is here for you, Conan

Perhaps because he knows the answers to all the questions on Jeopardy! (or at least has them written down in front of him), Alex Trebek always comes off as the smartest guy in the room. Match that with his unflappable nature and pointed wit, and you've got a man who cannot be played the fool. That's a big part of why his cameo during the monologue of a 2014 episode of Conan, hosted by the self-deprecatingly self-aware fool that is Conan O'Brien, is so entertaining.

"I think that Alex Trebek is starting to lose it a little bit," O'Brien says, segueing into a montage of Jeopardy! clips seamlessly strung together so as to make Trebek appear cuckoo. For example, he "reads" this clue off the board: "Hugh Jackman is a hairy man with one saclike body cavity that looks like an older dog with thick fur who was put to sleep for making a fool of himself." The correct response: "The musk ox." 

At the end of the package, Trebek strides out onto the Conan stage, sternly shaking his finger at O'Brien as the audience roars. "Hello, Conan," Trebek says. "You seem to be having a good time here today." O'Brien sheepishly apologizes, but Trebek waves it off. "I'm a big guy. I can look after myself. But I'm here for another reason. I'm worried about you," he says before throwing to another clip montage, this one edited to make O'Brien look like a rambling loon.

Merry Christmas, Alex Trebek

In 2014, Stephen Colbert won a coveted seat in network late-night, selected by CBS to replace the retiring David Letterman as host of The Late Show. That meant he had to give up his Comedy Central series The Colbert Report, where for nine years he'd hosted in-character as a blustery, confidently ignorant parody of a cable news personality (who also happened to be named Stephen Colbert).

To end The Colbert Report in a grand and notable fashion, Colbert called in the services of another take-charge TV personality: Alex Trebek. The final scene of the series finds Colbert asleep on the shoulder of a very uncomfortable-looking Trebek as they ride through the night sky in a flying sleigh. "Stephen, wake up," Trebek says, jostling Colbert awake. "It's time." Colbert then gives a heartfelt speech thanking his crew and their families before singing off, "From eternity, I'm Stephen Colbert." So apparently Colbert (the character) and Trebek (the game show host) hijacked Santa's magic sleigh to fly into forever together.