Matthew Drudge was raised in Takoma Park, Maryland, near Washington, DC. His parents are Reform Jewish Democrats who both worked for the federal government, and he is their only child. His father, Robert Drudge, a former social worker who owns the reference site www.refdesk.com and his mother, a former staff attorney for U.S. Senator Ted Kennedy, divorced when he was six. Drudge went to live with his mother. He had few friends and was an avid news reader and radio talk show fan. In his book Drudge Manifesto, Drudge reports that he "failed his Bar Mitzvah", and graduated 341st out of a class of 355 from Northwood High School in 1984, thus giving himself, in his words, a "more than adequate curriculum vitae for a post at 7-Eleven".
In an article for New York Magazine, Philip Weiss says Drudge was arrested on June 18, 1981, for making harassing telephone calls, and that Drudge went to live with his father on a farm on the eastern shore of Maryland. Weiss adds Drudge's father sent him back to Washington to live with his mother, who was unemployed at the time. Drudge was placed in psychiatric treatment with Jewish Social Services and it was recommended that he be sent to a boarding school, "and if not the last choice will be a foster home" (from court papers).
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.
Andrew Breitbart helps run the Drudge Report website. Breitbart met Drudge in Los Angeles during the 1990s when Drudge was a self-described "untrained D student." Drudge mentored Breitbart until 2005. Breitbart stated that he was "amicably leaving the Drudge Report after a long and close working relationship with Matt Drudge." He now runs Breitbart.com, but still helps run Drudge's website from Los Angeles. Breitbart, who describes himself as "Matt Drudge’s bitch", works the afternoon shift at the Drudge Report. Drudge frequently links to Breitbart's site, but does not get paid for this service, although it does provide Breitbart with income. Drudge has said that he holds no financial stake in Breitbart.com nor does he receive any compensation from its founder.
In the 1980s, Drudge worked as a telemarketer for Time-Life Books with his friend Craig Seymour. Seymour wrote in his autobiography that Drudge loved Whitney Houston, Chaka Khan and The Young and the Restless.