Cullen Ryan on Option, Option, Option: The Hidden Work of Adapting on Stage

In this "Who's This For" episode, I had a fantastic chat with my good friend, comedian Cullen Ryan, to really dig into what makes a comedian truly connect with an audience. We quickly got into the nitty-gritty of how top-tier performers go beyond just having great jokes. Cullen broke down how years of dedicated practice and meticulously honing their craft are the real secret sauce. It's about developing impeccable timing, precise pacing, and that crucial ability to adapt on the fly. He shared how the most seasoned pros have told their jokes literally "a thousand times," building an almost intuitive sense that allows them to pivot seamlessly if something doesn't quite land—they always have an "option, option, option" ready to go.

The conversation then shifted to something I've always found fascinating: the repetition of material. I asked Cullen if saying the same jokes over and over ever feels stale. He was quick to point out that it absolutely doesn't! He put it brilliantly, comparing it to a musician playing a G major chord—if the song calls for it, that's what you play. For comedians, every room, every audience, and even their own energy on a given night is different, creating an infinite array of possibilities that keeps the performance fresh and dynamic. It's a powerful reminder of the constant learning and razor-sharp adaptability needed at the highest levels of any craft, not just comedy.