December, 1953: Hugh Hefner releases his first issue of Playboy magazine featuring Marilyn Monroe on the cover. Now, countless celebrities have graced the cover of Playboy, something that is considered an honor today. But how has Hefner's lifestyle brand fared against the explicit tastes of today? Watch Playboy's brand evolution throughout the years and find out.

[Photos: COURTEST OF PLAYBOY (VARIOUS PLAYBOY COVERS); JULIEN’S AUCTIONS/CORBIS (MARILYN MONROE COVER); ADVERTISING ARCHIVES/ALAMY (70S PLAYBOY COVER); ADVERTISING ARCHIVES/ALAMY (80S PLAYBOY COVER); EVERETT COLLECTION HISTORICAL/ALAMY (HUGH HEFNER 1950S); BETTMANN/CORBIS (HUGH HEFNER); EVERETT/EVERETT (INTERNATIONAL COVER); RAYMON BOYD/GETTY (PLAYBOY MANSION); CHRIS HOWES/ALAMY (PENTHOUSE MAGAZINE); HULTON-DEUTSCH COLLECTION/CORBIS (VLADMIR NABOKOV); COURTESY OF PLAYBOY (BW HEF WORKING IN BDROOM); CHRISTOPHER FELVER/CORBIS (KURT VONNEGUT); CORBIS/CORBIS (JOHN UPDIKE); NBC/GETTY (PHYLLIS DILLER SHOW); PRESSELECT/ALAMY (PLAYBOY PRODUCTS); JACK SULLIVAN/ALAMY (PLAYBOY PURSE); PRESSELECT/ALAMY (PLAYBOY PRODUCTS); COURTESY OF PLAYBOY (HEF WITH GND FROM ISSUE); SPLASH NEWS/CORBIS (HOLLY MADISON); BETTMANN/CORBIS (BUNNIES) ]