Recently, Bill Cosby cancelled an appearance on David Letterman’s show after multiple women claimed that Cosby long ago had slipped something in their drinks to molest them.

Cosby and Letterman have something in common besides being popular comedians: they’ve both had somebody thrown in jail for blackmailing them.

Back in 2009, using the Letterman and Cosby cases as examples, I asked:

Why Is Blackmail Illegal?

And then came back to the subject the next day with

Legal v. Illegal Blackmail

Rereading the comments, I’d conclude that there are indeed good reasons for blackmail being illegal, but they are kind of subtle.

It’s worth asking if the 1990s case in which Cosby got a young woman sentenced to five years in prison for asking for a big payoff to keep quiet about her being his daughter (Cosby responded that she wasn’t his daughter and he’d only slept with her mother once) may have discouraged other women from coming forward. A good lawyer could no doubt explain the precise legal differences between the imprisoned woman’s case and yours, but the five-year sentence for blackmail had to be so frightening that it seems likely that it might have shut some women up.

As for Cosby’s character, I never really believed the America’s Dad stuff because I could remember him hanging out at the Playboy Mansion for what seemed like most of the 1970s.

Also, the “Cosby never worked blue” meme doesn’t jibe with my memories. My parents went to see Harry Belafonte at the Hollywood Bowl in the summer of 1971, but Belafonte was sick, so it was announced to patrons that Cosby would fill in for his friend. My parents thought that sounded good because they knew how much I liked his early records like “Noah” and his 1969 sit-com. But, they reported back, Cosby’s material that night was shockingly obscene, and they didn’t like that at all. That could just be my parents over-reacting, but it fit in with the Playboy Mansion stuff.

My general impression was that Cosby’s star was fading throughout the first half of the 1970s, which I thought unfortunate because I found him hilarious. But then the Jello Pudding commercials rebuilt his popularity on the basis of avuncularity, from which he segued into his immensely popular 1980s sitcom (which I didn’t find hilarious).

On the other hand, I know a fellow who played a minor recurring character on the 1980s sitcom. He’s a good guy and he looks up to “Mr. Cosby” as a role model. So, the reality, whatever it was, is complicated.

Veteran commenter James Kabala, who worked hard back in 2009 to explain blackmail law to me, comments:

I think we discussed this at the time of the Letterman case – blackmail is not “coming forward.” Blackmail is NOT coming forward and then getting money out of it too. A blackmailer only goes public if he fails in his attempt to get the money. The blackmailer prefers for his mark’s bad deeds to go unpublicized. If they were publicly known, then there is nothing to get paid off about.

Sure, but you had to explain blackmail law to me about 3 times before I finally started to understand it.

If I were some actress/model/whatever who heard about Cosby sending an accuser to prison for five years, how confident would I be that I understood the law well enough to risk accusing somebody who evidently has that kind of mojo and is that merciless? And am I all that sure he really did put a Mickey Finn in my drink? Or maybe I just had too many drinks? Is it impossible to imagine that Bill Cosby charmed me into having too many drinks? Maybe I sort of drunkenly agreed to take a Quaalude to make a certain sexual practice less painful? It’s all kind of in a Seventies haze …

What’s going on now is that lots of these women are hearing each other accuse Cosby of putting something in their drinks, so that adds credibility to their suspicions that they didn’t really drink that much the time they slept with Cosby.

But that kind of thing can sometimes turn out very wrong, like UFO sightings built on drunk drivers’ vague experiences, for which their reading about other drunk drivers’ claims provides them a vocabulary of details to cite.

So, I don’t know. But that’s why I think things like the blackmail incident and all the times he was on TV hanging out with Hef in the 1970s are moderately informative.

In contrast, say that during the 2012 election, wave after wave of women came forward accusing Mitt Romney or Barack Obama of drugging and raping them. That could be true, I suppose, but it doesn’t fit with much else we publicly know about them. There is just not much evidence of either one chasing tail very much.

In contrast, we have public record of of Cosby being a big league tail-chaser from all the TV shows from the Playboy Mansion he appeared on that everybody has forgotten about. And there’s the 1997 blackmail case. But that also doesn’t mean he’s guilty of drugging and raping women since it looked like plenty of women were enthusiastic.

So, we’ll see …