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.

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."

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.

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.

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?

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.

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.