With Conan O’Brien saying goodbye to his show at TBS this week, the ginger-haired late-night host also delivered a proper sendoff to his least favorite employee, associate producer Jordan Schlansky. It’s been a long road for these two frenemies. Schlansky first started regularly dropping by to irritate his boss on NBC’s Late Night With Conan O’Brien with inane facts, obnoxious Eurocentric elitism, and a complete disregard for the chain of command. Schlansky’s refusal to treat Conan as his boss by logic-ing his way out of workplace responsibilities has been a beloved staple of the show over the last ten years. With that in mind, let’s take a look back at five of our favorite moments from Jordan and Conan’s awkward relationship. Arrivederci, Jordan, we hope to see you on HBO!
The state of Jordan’s office has been a running gag on the show for the last decade. Despite his obsession with body hair removal and his overall appearance, Jordan’s office reveals that he’s quite a slob. Inviting the Property Brothers to renovate Jordan’s office, Conan steps into conversations he probably doesn’t want to have, such as whether or not Jordan poops at work. The discovery of two Squatty Potties in his office doesn’t do much to clear up the mystery, but Jordan’s admiration for the brothers’ body-grooming rituals is revealing enough. Once again, Jordan frustrates Conan by reversing the line of questioning; he attempts to discover Conan’s bathroom schedule, leading to the hilarious re-contextualization of an old Sean Penn interview. Sadly, Drew and Jonathan never finished the reno due to the pandemic. Instead, they treat us to a disturbing 3-D rendering of Jordan encased in his new office, which more than makes up for the segment’s unfinished state.
Aside from coffee, Jordan’s main obsession is the country and culture of Italy. A cranky, fake Italian (as a sign outside his office reads), Jordan escorts Conan to his boss’ favorite Italian restaurant, the Olive Garden. The segment is a reversal of their Italy trip, with Conan now gaining the upper hand over Jordan’s snobbishness. Conan ridicules Jordan’s Italophilia by demanding the waiter to “cheese it up” with a parmesan gun and forces Jordan to consider drinking an “Italian Margarita.” It’s always satisfying to watch Jordan temper his “expertise” when attempting to be polite, but it becomes a real “taste of Italy”-sized meal watching him do so in a tuxedo.
The state of Jordan’s office and his mysterious job responsibilities come to a head when Conan discovers that Schlansky doesn’t arrive at the office until after lunch on Fridays. Seated in Jordan’s office and waiting for the missing associate producer to arrive, Conan finds plenty of material to mock his employee for—a travel-sized pepper mill, a kaiser roll, two vintage Star Wars figurines, etc. Things don’t get easier for Conan when his unflappable straight man shows up. Jordan’s unfazed by his tardiness, arguing that he’s able to complete his (various) tasks in the time he’s there. Conan’s frustration with this reasoning leaves him without recourse, resorting to slapstick punishments, like forcing Jordan to remove his shirt and wear a giant clock, like Flavor Flav with a shaved chest.
One of Jordan’s earliest appearances on Conan’s TBS show doesn’t disappoint. In addition to a tour of the maze that leads to Schlansky’s office, Conan takes a step inside Schlansky’s unrelenting snobbishness, his frustrating logic (“I don’t have it. It’s here, but I don’t have it.”), and a peek behind the curtain into what exactly Jordan does for the show (“various tasks”). It’s textbook Schlansky, who creates logic puzzles that fluster his boss in an attempt to avoid responsibility for using company money to buy an espresso machine. Conan and Schlansky are best when they’re fighting for control, but Conan’s the boss, and his gift to Jordan of a “blood-stained” Mr. Coffee is more than a fitting button to a great segment.
The crème de la crème of Schlansky segments, “Conan Visits Jordan’s Favorite Restaurant” is the main event of their trip to Italy (Conan and Jordan’s espresso tasting being a close second). What’s great about this clip is how it shifts the power from Conan to Jordan, giving him an opportunity to mock his boss. (“In 2002, you were gross. If I look at a show from 2002, it looks like you were digitally manipulated.”) Jordan goes in on Conan, who’s having a ball putting ketchup on his steak and describing his wine as having notes of “desperation” and “feeling the need to concoct fake identities.” The whole thing ends with Curb Your Enthusiasm’s theme song playing while the restaurant owner watches these two bickering back and forth over who’s better known in Italy. It’s *chef’s kiss* molto buono.