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.”