Whether you regard the examples above as creepy lechery or benign flirting, this way of communicating is a part of David Letterman’s legacy.

Remember when a 2009 extortion attempt led to Letterman admitting to sleeping with female staff members who worked on his show? Letterman said:

I was worried for myself, I was worried for my family. I felt menaced by this, and I had to tell [the police] all of the creepy things that I had done...The creepy stuff was that I have had sex with women who work for me on this show. My response to that is yes, I have. I have had sex with women who work on this show. Would it be embarrassing if it were made public? Perhaps, it would, perhaps it would, especially for the women...It’s been a very bizarre experience. I felt like I needed to protect these people. I certainly need to protect my family. I need to protect myself. Hope to protect my job.

And so he did. The last episode of The Late Show With David Letterman airs tonight.