Conan O'Brien made history by premiering a clip from his dramatic film on *The Late Show*, marking a major career shift.

Conan O'Brien made history on September 29, 2025, becoming the first late-night host to introduce and play a clip from his own dramatic film, *If I Had Legs I'd Kick You*, during a guest appearance on *The Late Show With Stephen Colbert*. The film, set to premiere October 10, 2025, stars O'Brien as a therapist alongside Rose Byrne, Christian Slater, Danielle Macdonald, A$AP Rocky, and Ivy Wolk. The moment marked a major career shift for O'Brien, who has long been known for comedy and talk shows. During the appearance, he also reflected on the state of late-night television, offering lighthearted yet poignant remarks about industry changes, including Colbert’s upcoming exit after 33 years, while expressing deep admiration for his colleague’s impact and authenticity.