When it debuted: 2010
Segment lowlight: The numerous instances of plagiarism.
Much of what Leno shows during these segments is funny. That's because the material isn't his. Creating a segment that allows you to embrace the fact that you don't make up your own material is dastardly enough, but Leno sinks to new lows here.
There are several reports of the nefarious lengths Leno will go to not only to use material that isn't his on the show, but also to take credit away from the creators. One example of this ridiculous behavior is explained in full detail by one of the victims of his Jay's sticky fingers in the letter above.