Conan O' Brien on Hosting The Oscars A 2nd Time, The Magic of Chris Farley & Bits With Will Ferrell

TL;DR

Conan O'Brien discusses hosting the Oscars a second time, his prep process, Chris Farley memories, and the parallels between comedy and athletic performance.

Key Points

• 1.Conan's Oscars prep involves two months of work and secret club sets. He tests material at obscure clubs — including one behind a bowling alley in Covina where he urinated in an alley five weeks before the ceremony.
• 2.The Kendrick-Drake joke was his standout from the 2024 Oscars. The line 'it's time for Kendrick Lamar to call Drake a pedophile' destroyed the room; producer Jeff Ross bet $100 against the writer it would bomb — and lost.
• 3.Conan's writing team has longtime overlap between his late night, podcast, and Oscars work. Jason Kelsey's own late night show used former Conan writers including John Glazer, Tammy Sager, Andy Blitz, and Kevin Dorf.
• 4.Conan met Chris Farley on the day Farley waited to interview with Lorne Michaels at SNL. They spent 20 minutes walking the studio shouting fake orders at crew doing their jobs — a spontaneous bit that bonded them instantly.
• 5.Norm MacDonald is Conan's pick for greatest guest. He would fabricate elaborate personal stories in real-time — like owning a farm and having three daughters — treating them as performance art, leaving Conan predicting people will discuss him for 50 more years.
• 6.Tom Cruise surprised Conan as an underrated comedic guest. Filming together in London, Cruise was naturally funny with strong ideas, dismantling Conan's preconception of him as purely an action star.
• 7.Conan's core philosophy on interviewing: find your genuine interest and actually listen. Even with uninteresting guests, he hunts for one hook — a hobby, an odd fact — and warns that audiences always detect when a host isn't truly engaged.
• 8.He likens comedy preparation to athletic muscle memory. Thousands of reps eliminate conscious thought, freeing mental space to improvise when something unexpected happens — the same principle Travis uses to describe 'blacking out' on the field.
• 9.Will Ferrell ranks alongside Norm as a standout guest, appearing fully in character as a leprechaun in a thong. Conan also tried serious acting in the film 'If I Had Legs, I'd Kick You' with Rose Byrne, who received an Oscar nomination.
• 10.Conan committed on air to letting the Kelce brothers inject him with Toradol and jump through a flaming table. He declared it 'not a bit,' noting only that his wife would sue everyone involved afterward.