Ian Kerstein wrote:

Aaron, how could we not count this as a favourite! It's a terrific picture by your father - my goodness me, there's real talent there!!! Imagine if your jokey friend knew a little more, he could have even more joshingly suggested "Pin the Toupée on Bing" - or was he being kind (unlike me)?
Did your father at the time know that Sinatra painted? 

I also have a copy of "The Complete Crosby", published as a follow up edition to Charles Thompson's "Bing" (1976) to cover his death.
I've asked around Bingland but to no avail - do you happen to know what became of Charles Thompson? 
Since his 1981 biography: "Bob Hope: Portrait of a Superstar", he seems to have disappeared without trace. The Lord Lucan of Crosbyana. 
 

I can't remember if Dad knew that Sinatra painted or not back then. Not sure if he still would know or remember now. Dad is a compulsive. I'm sure he would have had a look through my copy of the book Nancy wrote on her father, which of course has some of Frank's paintings in.

I think Dad would have signed it F.Sinatra as a joke on the Crosby/Sinatra rivalry. Dad didn't like the drawing. He thought it didn't quite capture Bing. Therefore, it was a bad picture so therefore sign Sinatra's name as he would have deliberately set out to do a bad picture of Bing. 

I do have another photo of the picture. Dad added the signature and the pipe smoke as an after thought.

Pantelis, Thank you! I am having a rough few years but hanging in there. I miss all of you, I must try to be at next meeting. Aaron, So sad you don't have that drawing but at least you have photo of it.