If you are old enough to remember the Playboy magazine's Golden Era, they used to run ad's in the magazine with that question, designed to show potential advertisers how cool, hip and sophisticated the readers were. Typically a very successful guy, maybe in his 30's, who drives a luxury sports car, has the best stereo equipment, drinks top shelf booze, dresses stylishly, takes vacations to exotic locations and is of course always surrounded by a beautiful woman. So in a National Lampoon parody of the early 70's they ran the "What Sort of Man Reads Playboy" ad that had a picture of a bathroom stall, with the magazine on the bathroom floor opened to the centerfold spread, in front of a pair of legs with their jeans and underwear pulled down by their ankles above their Converse tennis shoes, obviously belonging to an adolescent boy and you can obviously guess what he's doing.
Which at the heart of it was what Playboy in its day was really about. For every reader who was the hip, good looking guy with plenty of disposable income who attracted gorgeous women, there were at least a dozen other readers who didn't fit into that peg. Teenage (and pre) boys who lived with their parents and kept their issues hidden from mom. College boys who had the centerfolds decorating the walls of their dorm or fraternity residence. GI's, sailors, prisoners. While Playboy did have some interesting articles, the superbly photographed pictorials of the semi-nude, drop dead beautiful women is what kept men buying the magazine at a time when any type of soft core erotica wasn't readily available.
"American Playboy" does a decent job of recapturing the history of the magazine and what was, at one time, truly a business empire and a delightfully hedonistic lifestyle Hugh Hefner indulged. It is done in a documentary style, with plenty of photos, rare film clips and cinematic reanactments. Matt Whelan does a good job of portraying Hef; he sounds exactly like him although their physical resemblance is slight as Whelan is a fairly big guy and Hef was a skinny runt. The story focuses heavily on the era of the 50's and 60's, the "Mad Men" period of Playboy and for the most part wraps up about 1980 after Playboy had its 25th anniversary. The final episode encompasses the past nearly 40 years as Hef handed over the reins of Playboy to his daughter, decided to get married and have kids (the marriage lasted 9 years) and then, in his 70's, deciding once again to self- indulge in the party lifestyle of his prime. Which brought us to the absolute silliness of the "Girls Next Door" reality TV series that lasted a few years in the 2000's decade.
If you read Playboy during their golden era you will enjoy this. Snowflakes be warned, plenty of T&A and I'm sure you will offended by what you would consider to be sexism and exploitation of females. As a historical piece, not sure of the accuracy of everything because it is produced by Playboy and as a result if presented from their POV.