A Tale of Two Playboys: The Divergent Paths of Hugh Hefner and Augustine of Hippo

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This is a tale of two playboys, their lives separated by about 1,500 years: Hugh Hefner and Augustine of Hippo. It is also a tale of two philosophers, and how their philosophies changed their lives, for better and for worse.

Hugh Marston Hefner, who died on September 27 at the age of 91, was born in Chicago. His parents were from Nebraska; his father was an accountant, his mother a teacher. Hefner “was the emotionally needy byproduct of Grace, a devout Methodist mother who never hugged him.”

“I was a very idealistic, very romantic kid in a very typically Midwestern Methodist repressed home,” Hefner said later. “There was no show of affection of any kind, and I escaped to dreams and fantasies produced, by and large, by the music and the movies of the ’30s.”

Augustine, who lived in North Africa and the Mediterranean during the decline of the Roman Empire, was born to his father, Patricius, a pagan (until a deathbed conversion), and to Monica, his mother, a devout Christian. Augustine was raised nominally Christian, though Monica’s persistent teaching didn’t take. Once, when the boy was seriously ill, he asked to be baptized. But upon his recovery, Augustine put off the sacrament for later.

A promising scholar, the adolescent Augustine, in his own words, was “floundering in the broiling sea of . . . fornication.” He later admitted that “the frenzy gripped me and I surrendered myself entirely to lust.”

Monica and Patricius sent their son off to Carthage to study. Yet he was anything but cloistered in the decadent city. Augustine indulged himself frequently. Eventually, he chose a mistress, with whom he remained for a decade as he became a noted teacher and speaker. She bore him a son, named Adeodatus. Eventually, at the urging of Monica, he would drop this mistress, only to take another, because “I thought I should be too miserable unless folded in female arms.”

Hefner’s youthful rebellion against his parents, and what he later called his “hurtful and hypocritical” upbringing, also turned to things sexual. In college, Hefner praised the now-debunked research of Alfred Kinsey that was published as “Sexual Behavior in the Human Male.” Hefner got his professional start at “Esquire” as an advertising copywriter, but he dreamed of starting a magazine, called “Stag Party,” that catered to both his unleashed sexual desires and his avarice. In a prospectus to investors, Hefner stated, “Sex is surefire.”

Indeed. The magazine got its investors, and readers and advertisers, in droves. The magazine that ended up being called “Playboy” popularized pornography, bringing it out of the shadows and into the parlors of America.

Hefner’s genius was to unhinge sex from marriage and children and link it to “sophistication” and “the good life.” As the magazine stated in its inaugural issue in 1953, “We enjoy mixing up cocktails and an hors d’oeuvre or two, putting a little mood music on the phonograph and inviting in a female acquaintance for a quiet discussion on Picasso, Nietzsche, jazz, sex.”

After Hefner became one of the architects of the Sexual Revolution, he went through three marriages and five other “partners,” some of them concurrently. Hefner’s philosophy could be summed up in this statement he gave to the “Los Angeles Times” in 1992:

“Much of my life has been like an adolescent dream of an adult life. If you were still a boy, in almost a Peter Pan kind of way, and could have just the perfect life that you wanted to have, that’s the life I invented for myself.”

Augustine’s philosophy, however, would change. After becoming professor of rhetoric for the city of Milan, he started going to the cathedral to hear the powerful preaching of Ambrose, the bishop. The brilliant truth of Christ attracted Augustine, but still he held back. “Give me chastity,” the rhetorician prayed, “. . . but not yet.” The playboy would not give in without a fight, but something deeper than carnal pleasure was calling.

One day while wrestling with these matters, Augustine was alone in his garden. He heard a child’s sing-song voice nearby saying over and over, “Take up and read.” He had been studying some of Paul’s epistles, and so he read the first thing he saw. It was from the Book of Romans:

Let us walk properly as in the daytime, not in orgies and drunkenness, not in sexual immorality and sensuality, not in quarreling and jealousy. But put on the Lord Jesus Christ, and make no provision for the flesh, to gratify its desires.

Suddenly the dam burst, not in licentiousness, but in liberty. “No further would I read,” he later said, “nor needed I: for instantly at the end of this sentence, by a light as it were of serenity infused into my heart, all the darkness of doubt vanished away.”

Eventually, Augustine became a priest, and then bishop of the city of Hippo. His writings, including his “Confessions,” provided hope even as the Roman Empire tottered, and they helped set the course of the church for the next thousand years. Augustine, though he never quite made peace with God’s gift of married sexual fulfillment, nevertheless helped those who followed to see that only God, not this world, can fulfill our deepest desires.

“Thou hast made us for thyself, O Lord,” he wrote, “and our heart is restless until it finds its rest in thee.”

And Hefner? He was beginning to experience the awful truth about sin enunciated by Screwtape: “An ever increasing craving for an ever diminishing pleasure is the formula.” In 2001, a former Playmate told “Philadelphia” magazine of the miserable pit of degradation into which the old man had fallen”

The heterosexual icon . . . had trouble finding satisfaction through intercourse; instead, he liked the girls to pleasure each other while he masturbated and watched gay porn.

How did Hugh Hefner sink so low, while Augustine of Hippo soared so high? They were both sinners. Augustine might say that, by God’s grace, one’s love must be rightly ordered, so that the most lovely things are loved the most; the least lovely, the least. That is a philosophy worth living, no matter the century.

Perhaps Hefner, a prominent advocate of loveless, commitment-free sexuality, might eventually have agreed. As the porn magnate once admitted in his later years, “I’ve spent so much of my life looking for love in all the wrong places.”

In making every provision for the flesh and none for what could truly satisfy his restless heart, Hefner walked down a dark path that turned his adolescent dreams of the good life into a hellish nightmare.

God, have mercy.

Stan Guthrie is an editor at large for Christianity Today and for the Chuck Colson Center for Christian Worldview. His latest book is “The Seven Signs of Jesus: God’s Proof for the Open-Minded.” 


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  • gladys1071

    both Hugh Hefner and Augustine were wrong. Augustine went too much the other way and he even villified married sex, so i have no love for Augustine, i think he villified sex too much because of his own shortcomings which in my opinion damaged Christians view of sex. Sex is not to be villified or glorified, it needs both a healthy balance of its meaning and at the same time should not be glorified to somekind of spiritual experience either.

    Both Hugh Hefner and Augustine in my opinion damaged the view of sex, to either too prudish or too liberal, the truth is somewhere in the middle in my opinion.

    • Stan Guthrie

      I agree that Augustine got a lot wrong, but he got a lot right, too. My purpose was not to offer a detailed critique of his views, though I tried to mention them in passing.

      • gladys1071

        I understand. I happen to think Augustine did a lot of damage to Christians view of sex, he caused people to see sex as sinful and dirty, instead of something God created for pleasure and bonding and procreation. To this day, his writing still affect people’s warped view of sex.

        As far as pornography, it has always existed, if you dig up the ruins of ancient city of Pompei, it is rampant , so Hugh Hefner did NOT invent pornography.

        I think we need to study history and we will find that their is “nothing new under the sun” the sexual inmmorality of today has always existed for as long as humans have been on this earth.

        • HpO

          In my comment above on Augustine, I made reference to 4th and 5th century version of porn-addiction and adultery, whose contemporary versions are now holding my fellow born-again Christian brothers and sisters – clergy and laity alike – in captivity. I opined that Augustine will be of no help to them to get out of this sinfulness, as he didn’t prove liberation from it either. Your comment resonated for that reason; thanks.

          • gladys1071

            That is because we are never really completely liberated from our sinful bent as long as we in these bodies, we remain subject to corruption, that is the human condition.

  • Zarm

    Once again, I am curious if the authors at Breakpoint view the same shows or webcomics that I do on their free time, as the article comes precisely at the time that a favorite webcomic brought up Augustine and introduced me to the man, not even a full day prior to reading the article.

    And an excellent article it is. Sobering, and eye-opening.

    • Stan Guthrie

      Coincidence … or the Holy Spirit? : )

  • Greg Schmidt

    Great article, Stan. Both had a profound impact on the world & culture, one for base & carnal degradation, the other for eternal Kingdom purposes. Thanks for this comparison, contrast and context it provided

    • Stan Guthrie

      Thanks, Greg.

  • gladys1071

    actually i don’t put them on pedestals at all.

  • HpO

    You know what, brother Stan Guthrie? Of “the Two Playboys”, I prefer the “Tale of … Augustine of Hippo” for its relevancy to believers. I think it’s because at the time of reading this article, I’m still reeling from the bad vibe I’m getting from this one line from Charisma News, “Shocker: Study Shows Most Christian Men Are Into Porn”, October 7, 2014: “Those who identify themselves as born-again Christians have similar struggles with pornography and affairs”! So I’m thinking, Hmm, maybe brother Augustine’s Confessions here can help them out of porn-addiction and adultery? But after taking notes from your article, it looks to me he was still trapped in them himself! Some help he is, as it turns out. Here are those notes: (1) “‘Give me chastity … but not yet.’ … Carnal pleasure was [still] calling.” In the porn-addiction-&-adultery version, apparently, from “1,500 years” ago? (2) “All the darkness of doubt vanished away.” But not “the darkness” of 4th and 5th century porn-addiction and adultery, apparently? (3) “Augustine … never quite made peace with God’s gift of married sexual fulfillment”! So, yeah, “God, have mercy”, indeed. And then some. But not just on Hugh Hefner, apparently. But on “those who identify themselves as born-again Christians”, too. Me included.

  • HpO

    Neither do I read gladys1071 putting anybody on “pedestals”. What gives? Why this remark? Is there a counter-argument from you in the offing perchance? No? So this “pedestals” word is to function as a silencer, then?

  • gladys1071

    i think that kind of thinking is still very prevelent today. The attack on contraception is an example of such. God forbid that anyone use contraception (even married couples) and enjoy sex just for its sake.

    I see t right through it especially the most recent applaud by many Christians about the contraception mandate being removed.

    Why would anyone object anyone use contraception? why because it is a subtle belief in sex is for procreation and again don’t want anyone to enjoy in the gift of sex that GOD CREATED.