1. Jaywalking (The Tonight Show with Jay Leno )
When it debuted: 1992
Segment lowlight: Jersey Shore Jaywalking
There have worse bits on late night than "Jaywalking." Many of them are on this list. We put "Jaywalking" at the top for its awful influence on the late night landscape. Every would-be late-night comedian seems to believe that making everyday people look stupid is required of any successful host. "Jaywalking" is largely responsible for this disheartening trend.
Stand-up comedians know crowd work is lazy, but at least in a club, you have to be honest with the crowd about who you are and lack the advantage that comes with the element of surprise. Walking up to people on the the street, waiting for "funny answers," and then editing for better results is shooting comedic fish in a barrel.
We wouldn't expect anything less from Leno, but we could do without dozens of imitators clogging the streets of Manhattan and L.A. trying to pull cruel gags on tourists. Here's hoping for more late-night innovation in the future and that these segments will show the next generation of late-nighters exactly what not to do.