Date: December 1953Hugh Hefner and his friend, Eldon Sellers, sold 53,991 copies of the first Playboy from a makeshift office in Hef's kitchen. The magazine, which was undated because no one knew if there would be a second, was enormously popular... thanks in no small part to Marilyn Monroe, who graced both the cover and the centerfold. And the articles, too, which everyone read.
Date: November 9, 1967
Rolling Stone's first cover was much less controversial than their latest: it featured a photo from story about the Monterey Pop Festival and a brief mention of the Grateful Dead ("a photographic look at a rock 'n roll group after a dope bust"), with John Lennon in "How I Won the War" on the cover. In 1967, a subscription was $5 for 6 months or $10 per year
More at Mental FlossDate: March 3, 1923The cover was a portrait of House Speaker Joseph G. Cannon. Content consisted of short news bulletins, an ad for All America Cables ("when time is short and minutes count use the direct cable facilities to Central America, South America, Cuba, Porto Rico other West Indies") and, strangely, imaginary interviews with Jack Dempsey, the boy Emperor of China, John D. Rockefeller, and Princess Yolanda of Italy.