The history of comic art commissions is not as well documented as, say, the history of comic books or the history of comic book fandom. Comic artists have been doing commissions since the early days of the industry, but it seems to have been a hidden endeavor - done on a small scale, through personal deals at conventions and through 'connections'. I truly envy those who got in on the ground floor (see
this link for an example of what I am talking about).
My first exposure to comic art commissioning was the advertisement you see before you. It was placed by Blackhawk and 'good girl' artist Bill Ward in the 1986 edition of the Overstreet Comic Book Price Guide. The fact you could have an artist draw a custom picture just for you blew my young mind. I never did write Bill - despite reading and re-reading that ad at least 1000 times - partly because $35 was a fortune to me at the time, and partly because I was absolutely terrified he'd draw a girl like the one you see in the ad and I'd have to explain it to my parents!
In retrospect, not writing Bill is a huge regret. I'm always keeping an eye out for pieces he did for collectors during this period, but they seem few and far between. Sigh. What might have been...