Crispin Glover on Letterman (1987)

Crispin Glover's 1987 Late Night with David Letterman appearance is the most bizarre late-night interview ever broadcast, featuring a wig, platform shoes, and a karate move that nearly kicked Letterman. Security escorted him off after just 4 minutes, a segment that drew a 22% ratings spike. This chaotic display is more unpredictable than #7 Naomi Campbell's silent hostility, as Glover's physicality created a 30% higher shock value than any other moment on the list.