Matt Drudge was unknown before he began the news aggregation site, the Drudge Report. For many years, he took odd jobs such as night counterman at a 7-Eleven convenience store, telemarketer for Time-Life books, McDonald's manager, and sales assistant at a New York City grocery store. In 1989, he moved to Los Angeles, where he took up residence in a small Hollywood apartment. He took a job in the gift shop of CBS studios, eventually working his way up to manager. Here, he was apparently privy to some inside gossip, part of the inspiration for founding the Drudge Report. Worried about his son’s aimlessness, Drudge's father insisted on buying him a Packard Bell computer in 1994. The Drudge Report began as an e-mail sent out to a few friends.
The original issues were part gossip and part opinion. They were distributed as an e-mail newsletter and posted to alt.showbiz.gossip Usenet forum. In 1996, the newsletter transitioned slowly from entertainment gossip to political gossip and moved from e-mail to the Web as its primary distribution mechanism.
In March 1995, the Drudge Report had 1,000 e-mail subscribers; By 1997, Drudge had 85,000 subscribers to his e-mail service. Drudge's website gained in popularity in the late 1990s after a number of stories which he reported before the mainstream media. Drudge first received national attention in 1996 when he broke the news that Jack Kemp would be Republican Bob Dole's running mate in the 1996 presidential election. In 1998, Drudge gained popularity when he was the first outlet to break the news that later became the Monica Lewinsky scandal.
Drudge met Andrew Breitbart in Los Angeles during the 1990s and became his mentor, with Breitbart later helping to run the Drudge Report. Breitbart announced in 2005 that he was "amicably leaving the Drudge Report after a long and close working relationship with Matt Drudge," but still helped run Drudge's website from Los Angeles by working the afternoon shift, in addition to running Breitbart.com. Drudge frequently links to Breitbart's site, but does not get paid for this service.