The Fifteen Funniest Bits From "Late Night With Conan O'Brien"

The tectonic plates of the talk show world shifted once again last night when Conan O’Brien made his debut as the fifth host of NBC’s legendary “Tonight Show.” In this reviewer’s opinion, it was a fairly strong maiden voyage. Conan’s monologue was on point, guests Will Ferrell and Pearl Jam were funny and rockin’ (respectively), and a hilarious catchphrase was seemingly born before the show even took its first commercial break (chant along with me now, kids: “Cir-cle, cir-cle, cir-cle!“).

Indeed, based on this one episode, the future looks bright for Conan O’Brien’s “Tonight Show.” Then again, who knows? Maybe Letterman will whip his dick out Wednesday night and subsequently murder Conrad O’Bunion in the ratings for the next year and a half. Anything can happen in this late shift game. Jimmy Kimmel got a show, fer chrissake.

I put together the following article a month or so before Conan relinquished his “Late Night” position to Jimmy Fallon (who I still say is doing an admirable job, considering his credentials) in the hopes some reputable publication would snap it up around the time of Big Red’s exit. No such luck. Thus, I present it to you now, in no particular order, the fifteen funniest bits from the Conan O’Brien era of “Late Night” (first draft). Enjoy the walk down memory lane.

1. Where’s Grady? The Search For Whitman Mayo: In January of 1996, “Late Night” wanted “Sanford & Son” actor Whitman Mayo to appear in a sketch; unfortunately, no one could find him. There wasn’t a soul on Earth who seemed to know where TV’s beloved Grady had run off to after sitcom success. Conan quickly launched a national search, which brought upwards of 20,000 calls to NBC reporting Whitman Mayo sightings. An Atlanta cable repair man eventually clued in Mayo’s mother to the stunt, who in turn got in touch with her son. On February 18, Whitman Mayo (who had actually still been acting on and off) made a grand entrance on to the “Late Night” stage, complete with pyrotechnics and dancers. A similar manhunt was later undertaken by Conan and his staff to locate the Shakin’ Guy from Michael Jackson’s “Beat It” video (also successful).

2. The First Episode Intro (“Good Luck, Lotta Pressure!): This pre-taped segment cold opened Conan’s “Late Night” debut in 1993 and found the nascent host encountering all manner of New Yorkers on the way in to his first day at the new job. Everyone Conan met reminded him of the intense scrutiny he’ll be under replacing David Letterman, including an angry Tom Brokaw. None of this appeared to bother the slap happy O’Brien…until he arrived at his dressing room at placed his large noggin into a pre-made noose. Luckily, the show began before the former “Simpsons” writer could properly hang and free himself from the incredible burden.

3. Norm MacDonald Eviscerates Carrot Top: On May 15, 1997, Conan had “Melrose Place” star Courteney Thorne-Smith follow unpredictable “SNL” funnyman Norm MacDonald as his second guest. McDonald stuck around for Thorne-Smith’s interview, gushing like an excited child about her beauty and talent (despite having only seen her once before on a rival talk show). It was all fun and games until the actress brought up her forthcoming movie with prop comic Carrot Top, Chairman Of The Board. Unable to contain himself, Norm interjected with numerous nasty and hilarious quips at the expense of Courteney’s red-headed co-star. The audience roared, Court buried her face in her hand, and talk show history was made.

4. Andy’s Sister: Before sidekick Andy Richter left to pursue various non-successful acting ventures, “Late Night” had a recurring gag in which the rotund Richter’s sister Stacy would visit the set and angrily deal with her massive crush on Conan. Stacy was played by future “SNL” superstar Amy Poehler, who didn’t look a day over twelve in her headgear and pigtails.

5. The “Walker, Texas Ranger” Lever: 2004 saw the introduction of what was perhaps “Late Night’s” most absurd piece of comedy—the “Walker, Texas Ranger” lever. After NBC merged with Universal, Conan announced he now had the right to show clips from the famously cheesy Chuck Norris syndicated drama on “Late Night” any time he pleased. A handle was installed by his desk that O’Brien could yank anytime he felt the need to spice things up with a little “Walker.” Taken out of context, most of the snippets the lever served up were utterly bizarre and gut-bustingly hilarious. The most famous of all? A segment in which a young Haley Joel Osment uttered the mind-fuckingly awesome line, “Walker told me I have AIDS.”

[WANTED TO HAVE YOUTUBE HERE, BUT NOTHING WAS GOOD ENOUGH]

6. Celebrity Secrets: This ongoing skit found various big-time celebrities sharing dark and disturbing tales from their allegedly sordid pasts. The creepy music and dimly lit atmosphere underscored what were often ridiculous admissions, including GNR guitarist Slash’s revelation that he could never choose between puppies or kittens (“Too close to call? No. Too cute to call.”).

7. Clutch Cargo Clinton: First appearing in September of 1993, Robert Smigel’s sexually-charged hillbilly impression of our 42nd President (in which only the writer’s lips were visible through a hole in a publicity photo of the real Clinton) quickly became a “Late Night” staple. It wasn’t until Bubba left office in 2000 that Conan retired the horny, “Nee-HAW!”-shouting caricature.

8. “How Did You Get This Job?”: Former “Late Night” host David Letterman stopped by Conan’s how for a friendly visit on February 28, 1994. At one point, Dave jokingly interrupted his replacement with the aforementioned quote. “Was it a theme writing contest?” the gap-toothed comedy vet wondered aloud. “Yes, it was a ‘What Would I Do With A Talk Show,’” O’Brien answered in his patented self-effacing manner. “And I was fourth.”

9. Kenny Rogers Fails Taste Test: Curious as to whether or not the famed country singer could tell the difference between his own Kenny Rogers’ Roasters brand chicken and a “Brand X,” Conan set up a taste test for Rogers when he appeared on a November 1996 episode of “Late Night.” To the shock of everyone, Kenny Rogers failed to pick the poultry that bore his name, which could be why you only find it at gas stations and malls these days.

10. Kilt Flash: Canadian fiddle player Ashley MacIsaac had a wardrobe malfunction years before Janet when he visited “Late Night” on January 9, 1997. Towards the end of his performance, MacIsaac kicked his legs up and gave America a nice tasty view of his meatballs. The blurred out clip quickly became the talk of Conan’s show for the rest of the week. Who knows how big it would have become had YouTube existed back then.

11. Triumph The Insult Comic Dog: When he first appeared in a February 1997 skit about extraordinarily talented canines from the Westminter Dog Show, no one could have known this gruff-talking hand puppet with the labored catchphrase (“For me to poop on!”) would eventually dominate “Late Night.” Triumph, operated by Robert Smigel, was easily the most popular of O’Brien’s wide stable of wacky characters, making a name for himself verbally attacking everyone from Pauly Shore to Bon Jovi to gaggles of anonymous Star Wars fans. Triumph’s popularity was such that the puppet even managed to release an album, Come Poop With Me, in 2003.

12. Pimpbot 5000: Combining the classic sensibilities of a 1950s robot with the dynamic flair of a 1970s street pimp, Pimpbot 5000 made his mark early on “Late Night” by alternately threatening Conan (whom he called “White Bread”) and speaking in hilarious rhyme. Personal favorite: “Got a nose full of candy and an ass made by Tandy!” On February 26, 1997, Pimpbot 5000 showed up to confront guest Ice T; quoteth the ‘Bot: “I haven’t seen you around the old neighborhood in a while.”

[ONCE AGAIN, YOUTUBE FAILS ME LIKE AN ILLITERATE SECOND GRADER]

13. Re-Release Dirty Dancing Campaign: Following the successful re-release of the original Star Wars movies, Conan O’Brien launched his own campaign to get the 1987 chick flick classic Dirty Dancing re-released in theaters. For a couple weeks in July of 1997, O’Brien stumped hard for DD, threatening to fire beloved band member La Bamba if Hollywood ignored his pleas. Surprisingly, the “Late Night” goof worked—Dirty Dancing hit screens once again that August. Later, Conan admitted he had the movie confused with Footloose or Flashdance. After seeing a clip of Dirty Dancing, the irreverent host called for a ban.

14. The Gaseous Weiner: This rather base giant hot dog character danced around the “Late Night” stage between 1993 and 1997, passing very noticeable gas to a specific musical sting. The writers spiced things up a bit with the Weiner by having him break his leg at one point; later, the character suffered from a serious bout of amnesia (the Weiner appeared in audience sans costume, married and unable to remember former life).

15. Clive Clemmons’ “Inappropriate!”: Flipping through cable channels on their desk-side TV one night in 1998, Conan and Andy came across a program in which fictional heavy metal guitarist Clive Clemmons presented some of his favorite awkward moments from every day life. Each clip ended with the British rocker enthusiastically exclaiming, “Inappropriate!” Words really can’t do this one justice—just watch this clip and try not to spit milk out of your nose.

HONORABLE MENTIONS: The Kiss-Ass Turkey, the Giant Frightened Corn On The Cob, “Conan Babies,” the “Max On Max” Sex Tape, Seven Foot Groucho, Frankenstein, Tomorry the Ostrich, the time Max threw marbles under the Smashing Pumpkins and they all slipped and fell down, the Slipnuts, the time Joey Ramone confused Andy with Conan when wishing the latter a happy birthday, the time Jennifer Garner tried to show Conan up about the past tense of “sneak” but then got served by the dictionary, the Fed-Ex Pope, Shoeverine, the time the guy from “The Office” exposed the fact Cadbury was lying about their eggs getting smaller, the time Conan went to Texas, the time Conan worked at the Canadian border, Pierre Bernard’s Recliner Of Rage, all those times that German Shepard shot somebody.

Any glaring omissions here, folks? Lemme know. Sound off in Das Commentz.

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