The first issue was published on February 16, 1990.
Created by Jeff Jarvis and founded by Michael Klingensmith, who served as publisher until October 1996, the magazine's original television advertising soliciting pre-publication subscribers portrayed it as a consumer guide to popular culture, including movies, music, and book reviews, sometimes with video game and stage reviews, too. ("the post-modern Farmers' Almanac").
In 1996, the magazine won the coveted National Magazine Award for General Excellence from the American Society of Magazine Editors. EW won the same award again in 2002.
In September 2016, in collaboration with People, Entertainment Weekly launched the People/Entertainment Weekly Network. The network is "a free, ad-supported online-video network carries short- and long-form programming covering celebrities, pop culture, lifestyle and human-interest stories". It was rebranded as PeopleTV in September 2017.