The 2000s proved to be another historic decade for Playboy, even though the entire magazine industry was trying to keep up with the pace of the web. Playboy remained ahead of the curve and was featuring content and its cover girls on the web since it launched Playboy.com in 1994 — way before the millennium hit. And the decade’s covers proved to be just as iconic as they were in the 50s. Kim Kardashian, Mariah Carey, Paris Hilton and Carmen Electra all posed for covers during the 2000s and became some of the brand’s most famous cover models. The January 2000 issue with cover art from Peter Marx even became a collector’s item, featuring the 100 most beautiful women of the 20th century. Playboy fittingly celebrated its 50th anniversary during the milenium, and looked forward to another decade of covers.