My feelings of him are mixed... I think he's a brilliant business man who has made an incredible name for himself and really wrote the book on promotions of a brand. I think he's a well-meaning individual who is somewhat naive regarding his accomplishments.
I agree that his spear-heading of the sexual revolution in the 60's was a historic achievement. Thing is, I think we're discovering now that the sexual revolution may have done a lot of damage to society. The free-love style of the 60's has done a great deal in de-valuing the importance and intimacy of sex. It led to the short-attention span, instant gratification view of sex, stripped of it's meaning and specialness. I think it's telling how much the divorce rates have risen following the sexual revolution. People have become more consumed with individual pleasure, than sacrifice and working towards a worthy whole. I think Hugh Hefner is a powerful figure in this. Now, I'm not saying that the harsh puritan beliefs were any better, in fact they were dangerous. I do believe however that the selfishness that's resulted from the sexual revolution is disturbing.
I also have reservations regarding Playboy's use of 18 year old models. Now, I know this applies to all porn or nude modelling, but the mentality of 18 year olds is very lacking in judgment and maturity. I remember when I was 18, and my sister is 18 now and I strongly believe that that age is not yet at a point where the gravity of the decisions and the implications that will follow are properly given attention.
Now, I'm not a religious person, which some of you may have assumed. My views are based on person observations of society and the people around me. Make of my opinion of you want. I just don't believe in buying into the "HEF'S THE PIMP!!! Attitude".