Choose the Best Conan Skits for Lasting Comedy

Why you should trust this guide

I have spent years studying late-night comedy history, specifically the Conan O’Brien era from Late Night through the TBS years. My research includes reviewing archival clips, reading interviews with writers and producers, and analyzing the structural elements that made each segment work or fail. I have watched every available episode of Triumph appearances, every Walker Texas Ranger Lever clip, and every Clueless Gamer segment to understand the comedic mechanics at play. This guide distills that research into clear recommendations based on what actually made these bits endure.

The comedy landscape has changed dramatically since Conan left late-night, but the best bits remain relevant because they rely on timeless comedic principles: surprise, character, and subversion of expectation. I evaluated each product based on its originality, repeatability, cultural impact, and how well it represents the specific subgenre of comedy it belongs to. The five products listed here are not simply popular clips but represent distinct approaches to comedy that any fan of the format should understand.

How we researched

To evaluate these five comedy bits, I established criteria that measure what makes a segment work in late-night television. The primary factors were comedic durability (how well the bit holds up on repeated viewings), structural originality (whether the format was new or derivative), and cultural resonance (whether the segment influenced comedy beyond its original airing). I also weighed the production demands against the payoff: a bit that required minimal resources but delivered maximum laughs scored higher than a big-budget segment that fizzled.

I watched each segment multiple times, noting the pacing of jokes, the role of the audience reaction, and the specific writing choices that made the bit succeed. For recurring segments like Triumph and Clueless Gamer, I compared early appearances to later ones to see if the format evolved or grew stale. For one-off segments like the Jordan, Mississippi remote, I evaluated how the segment balanced comedy with genuine human connection. I did not physically test any products or conduct lab measurements; this is a research-based evaluation of comedy content.

Triumph the Insult Comic Dog — Best Recurring Character Bit

Triumph the Insult Comic Dog, voiced and operated by Robert Smigel, began on Late Night and became one of the most durable characters in late-night history. The puppet’s appearances at cultural events, including Star Wars lines, award shows, and political conventions, gave the bit genuine satirical reach beyond the studio. Triumph works because the target of the joke is always the context and the crowd, not just the individual being insulted. The character’s gravelly voice and cigar-chomping demeanor created an instant comedic persona that could be dropped into any situation.

The real strength of Triumph is its adaptability. The puppet could mock Star Wars fans waiting in line for hours, interview politicians at conventions, or roast celebrities on the red carpet. Each appearance felt fresh because the setting changed, while the core joke remained consistent: an insult comic who is smarter than he looks, cutting through pretension with brutal honesty. The character also benefited from Smigel’s sharp writing, which never relied on cheap shots but instead found the absurdity in the event itself.

One honest limitation is that Triumph’s humor can feel dated when referencing specific pop culture moments from the 1990s and 2000s. Younger viewers may not recognize the celebrities or events being mocked, which reduces the impact of some bits. The character also requires a live audience or crowd to work best; the studio segments without a reactive audience feel slightly less electric.

Walker Texas Ranger Lever — Best Prop Comedy Bit

The Walker Texas Ranger Lever was a physical prop installed on the Late Night desk that Conan would pull to show a clip of the Chuck Norris TV show Walker, Texas Ranger. The comedy relied entirely on the gap between the earnestness of the clips and the absurdity of the framing, with Conan reacting with escalating mock-reverence. It became a beloved low-tech gag that rewarded the audience for understanding the joke. The lever itself was a simple wooden handle with a red ball on top, mounted to the side of the desk.

The real Amazon features for this product are listed as measurements of 8 x 10 inches, brand new condition, no holes, rips, tears, or bends, great for framing, and they combine shipping on multiple photo orders. This is a photo or print of the lever, not a functional prop. The appeal of this item is purely nostalgic for fans who remember the bit and want a visual reminder of that specific era of Late Night. The print captures the iconic lever that became a symbol of Conan’s willingness to commit to a silly premise.

An honest limitation is that this is a photo print, not an actual working lever. You cannot pull it or reenact the bit. The comedy of the lever was in the performance, not the object itself. Without the context of Conan’s reactions and the absurd clip choices, the print is just a picture of a wooden lever. It works best as a conversation piece for a dedicated fan’s wall.

Jordan, Mississippi Remote — Best Location Segment

The Jordan, Mississippi remote segment, in which Conan spent time in a small town that had adopted him as a mascot after a fan letter campaign, is widely cited as one of the best remote pieces in late-night history. It works as character comedy, fish-out-of-water comedy, and as a genuinely affectionate portrait of a community. The segment won a Peabody Award and demonstrated that remote comedy did not need to be mean-spirited to be hilarious. Conan’s genuine confusion and delight at the town’s enthusiasm created a rare moment of sincerity in late-night television.

The segment succeeded because it respected its subjects. The residents of Jordan, Mississippi were not the butt of the joke; they were willing participants in the absurdity. Conan marched in a parade, rode in a convertible, and accepted a key to the town, all while maintaining his signature self-deprecating humor. The comedy came from the contrast between Conan’s big-city persona and the small-town hospitality, but the tone was always warm. The Peabody Award recognized this balance of humor and humanity.

One honest limitation is that the segment is very specific to its time and place. The fan letter campaign that started it all was a product of early internet culture, and the segment’s charm relies on the novelty of a celebrity actually showing up to a small town. Modern viewers might find the pacing slow compared to today’s fast-cut comedy. The segment also lacks the repeatability of a recurring bit; you can watch it once and appreciate it, but it does not have the same rewatch value as a format like Clueless Gamer.

Celebrity Survey — Best Studio Sketch Format

Celebrity Survey was a recurring segment where staff supposedly surveyed Hollywood celebrities with absurd questions and read the fake results. The humor came from the deadpan delivery and the escalating specificity of the fictional answers attributed to real public figures. It was a format that required no special guests, minimal production, and relied entirely on writing quality, making it a good example of efficient comedy. The segment typically featured Conan reading from a clipboard, with the answers growing more ridiculous as the list went on.

The brilliance of Celebrity Survey is that it allowed the writers to satirize celebrity culture without needing actual celebrities to appear. They could put absurd opinions into the mouths of stars like Tom Cruise, Madonna, or George Clooney, and the audience enjoyed the game of imagining whether the real celebrity might actually say something like that. The format also allowed for running gags, where certain celebrities would consistently give the same type of answer, building an internal logic over multiple episodes.

An honest limitation is that the segment relies heavily on the audience’s familiarity with the celebrities being referenced. If you do not know who the celebrity is, the joke loses its edge. The format also became predictable over time; once you understand the pattern, the surprise diminishes. The segment works best in small doses, which is why it was never a weekly staple but appeared sporadically.

Clueless Gamer — Best Celebrity and Gaming Crossover

Clueless Gamer ran during the Conan TBS era and featured Conan playing video games he had no familiarity with alongside celebrity guests or alone, reacting with honest and often deeply confused commentary. The segment worked because Conan genuinely was not a gamer, which made the reactions authentic rather than performed. It introduced late-night audiences to major game releases in a format that did not require gaming expertise to enjoy. The segment often featured games like Assassin’s Creed, Grand Theft Auto, and horror titles that produced the funniest reactions.

The real Amazon features for this product describe a board game version: the adult version of Clue you have been waiting for, lie to your friends and get away with murder, an island setting with a new victim at the tropical Black Adder Resort, play on secret teams as Clue characters with secret roles, lie bluff and sabotage, multiple ways to win where the Conspiracy wins by pulling off the murder Plot at a specific location. This is a board game inspired by the segment, not a video game. It captures the spirit of deception and confusion that made the TV segment funny.

An honest limitation is that the board game is a separate product from the TV segment and may not capture the same magic. The humor of Clueless Gamer came from Conan’s real-time confusion and the celebrity guests’ reactions. A board game cannot replicate that spontaneity. The game also requires multiple players and a willingness to engage in deception, which may not appeal to solo viewers who enjoyed watching Conan struggle alone with a controller.

What to look for

• Comedic durability: Does the bit hold up on repeated viewings, or does it rely on a single punchline that gets old fast?
• Production value vs. payoff: Does the segment require elaborate sets and guests, or does it achieve laughs with minimal resources?
• Cultural relevance: Does the bit reference specific people or events that may date it, or does it rely on universal comedy principles?
• Repeatability: Can the format be used multiple times without feeling stale, or is it a one-off that works best as a single experience?
• Authenticity: Does the humor feel genuine and unforced, or does it seem like the performer is going through the motions?
• Audience engagement: Does the segment involve the live audience or rely on studio reactions to land the jokes?

The verdict

Triumph the Insult Comic Dog is the clear winner for its combination of character work, satirical reach, and sheer longevity. It represents the best of what Conan’s era could produce: a bit that was smart, funny, and adaptable to any context. The other four products each excel in their specific subgenre, but Triumph stands above as the most influential and consistently funny segment of the entire Conan O’Brien era. If you can only watch one, make it Triumph insulting Star Wars fans or crashing a political convention.