Comedian Brian Kiley spent nearly three decades inside Conan O’Brien’s late-night universe. A staff writer for 27 years across Late Night, The Tonight Show, and the TBS run of Conan, he won an Emmy in 2007 and earned 16 nominations along the way. These days, he’s back working with O’Brien again as part of Conan’s Oscars writing team—for the second straight year.
On this week’s episode of LateNighter’s Inside Late Night podcast, Kiley tells Mark Malkoff how his run with Conan began abruptly in 1994. Recommended by fellow Boston comics, he sent in a writing packet and was told he could start the very next day. There was even an unexpected connection: Kiley and O’Brien had attended the same Catholic Sunday school as kids in the Boston area.
Kiley recalls the relentless pace of late-night monologue writing, where producing 40 to 50 jokes a day was common. The workload intensified during Conan’s short-lived run hosting The Tonight Show, when the expanded monologue meant writers had to churn out even more material.
Alongside his writing career, Kiley also made 12 stand-up appearances on Conan’s shows—many booked at the last minute when a guest canceled. That same emergency-call role led to several appearances on Late Show with David Letterman, including his first spot, which came when Letterman was sick and Bruce Willis stepped in to guest host.
Kiley also shares some surreal backstage moments from his career, including returning to his Letterman dressing room after a set to find the members of U2 hanging out there.
Click the embed above to listen to Brian Kiley’s full conversation with Mark Malkoff now, or find Inside Late Night on Apple Podcasts, Spotify, or wherever you listen to podcasts.
For more Brian Kiley, visit his website or catch his 2022 Dry Bar stand-up special on YouTube.
