Today marks the twentieth anniversary of the first episode of Late Night with Conan O'Brien, a show that was famously predicted to be nothing more than a brief moment in the spotlight for some tall, pasty comedy writer. Instead, O'Brien sat behind the Late Night desk for sixteen years, playing the straight man against many surrealistic, strange, and/or just plain extremely silly characters in a response to the caustic, ironic, too-cool-for-school David Letterman years. O'Brien, original executive producer Robert Smigel, and a comedy hall of fame inaugural writing staff that included the names C.K., Odenkirk, and Stamatopoulos opted to build their Late Night show as an intelligent, possibly blatantly Dadaesque1 celebration of nonsense, which by 2009 helped carry Conan to The Tonight Show for…a brief moment in the spotlight (it was a whole big thing not worth mentioning). Now firmly entrenched and given free creative reign at TBS on Conan, O'Brien can celebrate twenty years on television today with a steady paycheck and some peace of mind, free to enjoy the following list of the twenty best characters from Late Night, The Tonight Show, and Conan while sipping a delicious beverage from his Eisenhower mug.
Andy's Little Sister
Before she became a member of Tina & Amy, and a main guest on any late night talk show she desires to visit, Amy Poehler appeared in multiple episodes of Late Night as Andy Richter's younger sister, a head brace rocking girl with a crush on Conan that would devolve into a ball of fury by the end of the scene. She would sometimes find her way on top of her unrequited love's back.
Awful Sports Chanter
Andy Blitz's funny PSAs in the early to mid aughts on how to keep a chant at a sporting event succinct, and not an excuse to reveal too much about being left back in the third grade for apparently six years because of a Spider Man comic, still hold up. They just refuse to stop, the only breaths taken for Blitz to implore the audience quickly to "come on" before continuing his oddly specific and humorously depressing personal stories.
Crooner Ghost Artie Kendall
Brian Stack's Artie Kendall character wrote a lot of pleasant enough sounding songs in the thirties. Unfortunately, they were offensive, misogynistic or racist. Fortunately, it's really funny, because Stack never stops using his humble, Bing Crosby voice when he admits that he was, not surprisingly, murdered.
In 1999, a.k.a. the halcyon days of pop music, boy bands ruled the world, and Conan O'Brien wanted to cash in. O'Brien's random propensity to use bowling analogies and to constantly change the names of the members of the boy band he was coaching were the funniest parts of this clip. One year later, Dudez-a-Plenti returned to the show in a Making the Video parody for their song "Awesome Girl," their follow-up to "Baby, I Wish You Were My Baby." In a perfect world, a worldwide tour with Three Times One Minus One would be in the works.
An early running gag that perfectly encapsulated what Late Night with Conan O'Brien was all about was "Emergency Guest", a robot Conan and Andy would use to fill in for a human that cancelled on them. It is programmed to make boring, generic talk show chit chat, a really funny joke on the standard, sycophantic interviews the show always looked to avoid. (It didn't help that O'Brien was a poor interviewer for the first few years.) It wasn't just a sly satire — the robot also would utter that "there is no need to panic," because it's a robot.
As you may have guessed, the FedEx Pope was created in the Late Night writers room when Brian McCann put a FedEx box on his head and began to bless people. O'Brien would repeatedly claim that FedEx Pope was one of the least liked and "the most terrible" character on the show, which would only just add to his infallible legend.
Hannigan the Traveling Salesman
Brian Stack clearly loves to subvert old fashioned wholesomeness, and to repeatedly call Conan a woman.
It kind of feels like cheating because the heckler bits are all about Eddie Pepitone, but the Bitter Buddha has been screaming at Conan since the Late Night days, and to our amusement has died in front of our eyes as both a 25-year-old and later, somehow, at the ripe old age of 22.
Even though he technically speaks exclusively in fragments, it is clear that The Interrupter has a very depressing life.
When Conan brought his TBS show to New York City in May 2011, I was fortunate enough to be in the audience at the Beacon Theater when the Masturbating Bear, thought to be the exclusive property of NBC, made his triumphantly disgusting return. I remember thinking how lucky I was to be able to witness first hand a floating bear jerking off twenty feet above us, and how sometimes you really shouldn't overthink comedy.
Mick Ferguson, the Bullet-Proof Legs Guy
Brian McCann's Mick Ferguson is rightfully proud of himself for not just having bulletproof legs, but to survive four gunshots straight to the heart. It's a testament to the talents of the writing staff that they can successfully do this sketch four different times with the exact same punchline each time and still make them all funny.
The 'No Reason to Live' Guy
These sketches can conceivably go on forever and not get tiring. McCann's character overreacts, screams that there is no reason to live, runs to a canoe on the top of the studio stairs and paddles off to his death, only to reappear claiming to be somebody completely different, taking something Conan said the wrong way, then screams that there is no reason to live, uses another mode of transportation to his death, and on and on and on. I love the added wrinkle of Conan always using different glasses every time he witnesses a death, particularly the opera glasses.
Conan always presents graphic designer Pierre Bernard as the perfect individual to articulate America's rage and dissatisfaction, but Bernard always spoke to a way too specific demographic to start any semblance of a revolution.
Conan knows more than anybody that androids have many uses besides as a last second guest if even Al Roker isn't available. Pimpbot has the pimping lingo down (I assume) enough to go toe-to-toe with Ice-T, who was years away from spending a disturbing amount of time trying to figure out what kind of people he's investigating over in the sex crimes unit.
Polly the NBC Peacock
NBC was so ahead in the ratings in the 1990s that network did not mind this recurring segment, which frequently had Conan asking Polly questions that contained actual truths about some artistically superior programming airing on rival networks.
Jon Glaser's character had the uncanny ability to ruin people's absurdly beautiful moments by uttering one measly word. In this clip, he tried to rattle the San Antonio Spurs before they played his beloved Knicks in the NBA Finals by saying his name as they entered their team bus. It did not work — the Spurs won in 5. To make matters worse, Pubes would later get a taste of his own medicine.
Robot Opera Singer Who Fights Crime
Robot Opera Singer Who Fights Crime! by tvnutboy
Sometimes you come up with the title first. Yet another robot related gag, but the first one that lets Andy Richter have some fun.
The Slipnutz were cursed from the start. First, they were booked on Late Night the same night as the heavy metal band Slipknot. In a great extension of that joke, Blitz, Glaser, and Stack were able to do their incredibly tame, wacky, brief physical comedy on stage at the Continental Airlines Arena for a Slipknot concert. The fans didn't seem too appreciate them. The gag continued a few more times on the show, even though they kept lying to O'Brien by performing the same act over and over again.
Conan hasn't stopped poking fun at his bosses even after leaving NBC, letting Will Forte ride on a stuffed buffalo as a very opinionated and coarse Ted Turner on his TBS show.
Triumph, the Insult Comic Dog
We all have our favorite Triumph bit. The Star Wars premiere. Occupy Wall Street. For me, it's surprisingly enough one of his most recent appearances, when Robert Smigel and his cigar chomping canine alter ego came to save Jack McBrayer from getting totally emasculated at at the infamously rude Weiner's Circle in Chicago.
1Look at the poster on the right hand corner of this pre-debut promo.