Conan O’Brien Needs A Friend

Staff Review With Brian Kiley

February 26, 2026

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  • Conan O'Brien and Brian Kiley share a decades-long professional and personal history, dating back to their childhood in Brighton where Kiley knew Conan's brother Luke. 
  • Conan highly values Brian Kiley's comedic contributions, citing him as the writer he relies on for major events like the White House Correspondents' Dinners and the Oscars, despite Kiley's reputation as the cleanest comic. 
  • The long-standing working relationship between Conan and Kiley is characterized by inside jokes and riffs, such as Kiley's 'vermicelli legs,' which Conan meticulously archives and never forgets, even if he forgets other things. 

Segments

Early History and First Meeting
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(00:07:07)
  • Key Takeaway: Conan and Brian Kiley’s relationship began in childhood at Catholic instruction class in Brighton, Massachusetts.
  • Summary: Kiley first met Conan through Conan’s brother, Luke, at CCD classes where they discussed Boston sports teams. Conan recalls Kiley visiting the Late Night offices around 1993, leading to a brief, awkward interaction before Kiley was hired as a writer shortly thereafter. Kiley’s first official day working on the show was March 15th, 1994, which coincidentally aligns with the date of the current year’s Oscars.
Kiley’s Comedic Persona and Riffs
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(00:06:01)
  • Key Takeaway: Conan frequently impersonates Brian Kiley performing extremely filthy material at the Apollo Theater, contrasting sharply with Kiley’s real-life clean comedy style.
  • Summary: Conan admires Kiley’s disciplined joke writing and clean stage presence, which makes the impression of Kiley doing blue material particularly funny. Conan’s running riff on Kiley involves his disciplined routine of performing filthy sets, then retreating to read books on Truman while wearing chinos and a blue blazer. Conan also maintains a long-running riff about Kiley’s underdeveloped leg muscles, comparing them to ‘vermicelli.’
The Vault of Unforgettable Riffs
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(00:08:42)
  • Key Takeaway: Conan commits specific, often embarrassing, details about his writers to memory as permanent ‘riffs’ that he will never forget, regardless of cognitive decline.
  • Summary: The ‘vermicelli legs’ riff on Kiley is so ingrained that Conan claims he would remember it even in a deep coma. Conan also cites an instant riff he made on writer Berkeley Johnson regarding his father owning a flag store 20 years prior. These specific, often absurd, details about staff members are stored in Conan’s memory vault for future comedic use.
Pre-Show Rituals and Room Reality
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(00:09:52)
  • Key Takeaway: The intense, often nonsensical, joke-testing sessions Conan and Kiley shared immediately before going on stage created a unique, private ‘room reality’ that is impossible to explain to outsiders.
  • Summary: Before major performances like the White House Correspondents’ Dinner, Conan and Kiley would spend time making up jokes they would never actually use, often acting out the crowd turning on Conan. These moments were hilarious within the writer’s room but made no sense when recounted later to family members. Conan and Kiley also enjoyed post-show meetings, sometimes rooting against guests to facilitate better post-mortem discussions.
Chris Christie Joke Obsession
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(00:21:14)
  • Key Takeaway: Brian Kiley was obsessed with writing jokes about Chris Christie’s weight, often incorporating any news story involving overturned trucks carrying food into the material.
  • Summary: Kiley consistently submitted jokes about Governor Christie, setting up scenarios where Christie would immediately travel to the site of any food-related accident, such as a truck spilling candied hams. Conan eventually accused Kiley of shooting out truck tires to generate material. This obsession continued until the writers were told to stop fat jokes, though Kiley’s humor still managed to sneak Taco Bell diarrhea jokes into otherwise serious submissions.
Favorite Collaborative Moments
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(00:25:40)
  • Key Takeaway: The White House Correspondents’ Dinner provided high-stakes validation when Bob Dole complimented one of Conan’s jokes, which was likely written by Kiley.
  • Summary: Kiley and Conan worked on material for the Emmy shows and the White House Correspondents’ Dinners, which Conan considers highlights. During one dinner, after a successful joke about term limits, Senator Bob Dole pointed at Conan and said, ‘Good term limits joke.’ Conan also recalls a favorite, though unconfirmed, Kiley joke about Luciano Pavarotti releasing a cologne.