When it debuted: 1999
Segment lowlight: Digital Jay falling between a pair of breasts belonging to a Wayne Newton fan.
Leno does it all. We discussed earlier how he can make awful segments out of almost nothing. Here is an example of the opposite, where an absurd amount of resources are wasted on a garbage bit.
Digital Jay is a Web 1.0 animated creation that travels through the Internet and then sometimes goes to real places and makes awful jokes. We imagine this segment will continue to get worse and worse in retrospect, as time marches on and the tech references grow more and more outdated. Stick around for the end of the video above and see how the Internet can somehow turn you into a cat.