While he didn’t die in complete obscurity by any stretch of the imagination, Wednesday’s passing of Hugh Hefner didn’t mark the end of an era so much as it served as a reminder of where the boundaries once were.

When Playboy magazine began in 1953 — featuring a up-and-coming young actress named Marilyn Monroe — Hefner was blunt about his intentions: “We want to make it very clear from the start, we aren’t a ‘family magazine.’ If you’re somebody’s sister, wife, or mother-in-law and picked us up by mistake, please pass us along to the man in your life and get back to the Ladies Home Companion.” The early content seems almost tame today, but what Playboy did was pull pornography out of the back alleys and off the wrong side of the tracks and bring it into the “respectable” mainstream. As Patrick Trueman, president of the National Center on Sexual Exploitation, wrote, “Hefner succeeded in making pornography seem as American as apple pie.”

Yet for all the jokes about only reading Playboy for the articles, the truth is that in its heyday 30 to 40 years ago, some of the best writers and thinkers out there were regular contributors, including William F. Buckley, who called Hefner’s approach to life the “Playboy philosophy.” Moreover, Playboy was certainly pornographic, but less crudely so than its main imitators in that late-1970s era of sex, drugs and rock n’ roll — Larry Flynt’s Hustler and Bob Guccione’s Penthouse.

As Ben Domenech puts it, “What separates [Hefner] from the more lurid members of his industry is an appreciation for manners and a particular form of American masculinity: he advised you to be a gentleman, not a cad, in your pursuit of the centerfold or the girl next door.” Not exactly a compliment.

“Gentleman” or no, however, Hefner’s legacy is one of coarsening American culture. Trueman runs down a number of statistics and provides insights on the effects of pornography on our society, but one doesn’t need any of those to know that once-taboo topics have been flung out into the open, and that which used to be seen only in peep shows in a town’s seedier section is now willingly cycled onto thousands of teenagers’ phones by young participants who don’t consider the consequences.

Those who have their eyes open can see that the decline in morals exhibited in Hefner’s lifetime puts us perilously at odds with what President John Adams warned about in 1798: “We have no government armed with power capable of contending with human passions unbridled by morality and religion. Avarice, ambition, revenge, or gallantry, would break the strongest cords of our Constitution as a whale goes through a net. Our Constitution was made only for a moral and religious people. It is wholly inadequate to the government of any other.”

Adams also added, “Statesmen … may plan and speculate for Liberty, but it is Religion and Morality alone, which can establish the Principles upon which Freedom can securely stand. … The only foundation of a free Constitution, is pure Virtue, and if this cannot be inspired into our People, in a great Measure, than they have it now, They may change their Rulers, and the forms of Government, but they will not obtain a lasting Liberty.”

Religion and morality were two casualties of the “Playboy philosophy,” as was, ironically, Hefner’s own business. As the Internet served up ever more explicit pornography, the Playboy media empire began to erode, and the magazine became a parody of itself for a time last year when it stopped featuring nudes. Beginning with local and syndicated television shows in the 1960s, Hefner even branched out into cable television in 1982 with the Playboy Channel before selling off his interest in the network four years later. By his last days, even the Playboy mansion wasn’t his anymore — and he only got half the asking price.

His own decline was something he had coming. As National Review’s David French writes, “It’s hard to calculate the damage he did, but the cultural rubble is all around us.” And The Daily Signal’s Katrina Trinko laments, “His work of mainstreaming porn will likely live on — and continue to hurt men and women — for many years to come.”

Of course Hefner saw it just the opposite. “By associating sex with sin,” Hefner once said, “we have produced a society so guilt-ridden that it is almost impossible to view the subject objectively.” But a truly objective view of modern American society — from its general coarseness to its sobering rates of abortion, illegitimacy and divorce — makes one wonder how much better off we’d be had Hefner stayed with his original avocation as a cartoonist.