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".

He was arrested on June 18, 1981, for making annoying telephone calls. After the arrest, Drudge went to live with his father on a farm on the eastern shore of Maryland. After a short time his 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).

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.

Drudge was unknown before he began the conservative 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, when he left to work for The Huffington Post website. 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.

From June 1998 to November 1999, Drudge hosted a Saturday night television show called Drudge on the Fox News Channel. The show ended when the two parties agreed to part ways. Drudge had refused to go on air, charging Fox News with censorship when the network prevented him from showing photos of surgery on the fetus of Samuel Armas. Drudge, who is pro-life, wanted to use a picture of a tiny hand reaching out from the womb to dramatize his argument against late-term abortion, but Fox's John Moody decided that that would be misleading because the tabloid photo dealt not with abortion but with an emergency operation on the fetus for spina bifida. Fox News charged him with breach of contract but, after Drudge issued an apology, Fox issued a statement calling the parting "amicable". His contract was originally set to run through February 2001.

Drudge hosted a Sunday night talk radio show — "The only time anyone will let me on the air," he claimed. The show, which was also named the Drudge Report, was syndicated by Premiere Radio Networks. He guest hosted for the conservative radio talk show host Rush Limbaugh. Drudge gained radio notoriety in the early 2000s by becoming a constant reference for news material on Limbaugh's, Sean Hannity's, and Mark Levin's radio shows. He was often acknowledged by Michael Savage as a source of topics for The Savage Nation.

Drudge left his position as radio host with Premiere effective September 30, 2007. He was replaced by Cincinnati, Ohio, radio station WLW's Bill Cunningham on the network and in most markets, though in a few larger markets, John Batchelor replaced him instead.

Drudge wrote a book with Julia Phillips in 2000 titled Drudge Manifesto. The book features a transcript of a Q&A session conducted at the National Press Club on June 2, 1998, which lays out Drudge'sraison d'être. It also contains copies of e-mails sent to Drudge by his readers, dialogues between Drudge and his cat, and extensive descriptions of parties Drudge has attended and how the celebrities there reacted to him. A review in the Washington Post summarised the book as follows:

Indeed, while Drudge Manifesto runs 247 pages, it takes a lot of filler to reach that length: 40 blank pages; 31 pages of fan mail; 24 pages of Drudge Report reruns; 13 pages of a Q & A that Drudge did at the National Press Club three years ago; 10 pages of titles and other book boilerplate; six pages of quotes from Drudge's favorite philosophers (Monica, Madonna, etc.); four pages of a chat transcript; three pages that include nothing but a large zero; two pages that include nothing but a large numeral 1; one page that includes nothing but a tiny zero; and one page that includes Drudge's favorite Web sites. Which leaves, in the end, 112 pages of new material, including nine pages of poetry.

Another review, this time from the Columbia Journalism Review, stated:

... the publication of Drudge's very odd memoir, Drudge Manifesto, a book described even by ardent admirer Andrew Sullivan as "subliterate." By any standard, Drudge's book is padded. Of its 247 pages, forty-one are entirely blank. Another seventeen contain just a number or a name ("George W. Bush") or a phrase ("you're boring"). It is a weird, stream-of-conscious mixture of telling readers how he got his stories and mocking his critics.

In their 2006 book The Way To Win, Mark Halperin and John Harris report that Republican National Convention chairman Ken Mehlman "kind of brags" (as CNN host Howard Kurtz puts it) about utilizing the Drudge channel. They also write that:

"Drudge, with his droll Dickensian name, was not the only media or political agent whose actions led to John Kerry's defeat. But his role placed him at the center of the game -- a New Media World Order in which Drudge was the most potent player in the process and a personification of the dynamic that did Kerry in."

In 2006, TIME Magazine named Drudge one of the 100 most influential people in the world, describing the Drudge Report as:

"A ludicrous combination of gossip, political intrigue and extreme weather reports ... still put together mostly by the guy who started out as a convenience-store clerk."

ABC News concluded that the Drudge Report sets the tone for national political coverage. The article states that:

"Republican operatives keep an open line to Drudge, often using him to attack their opponents."

In October 2006, Washington Post editor Len Downie, speaking at the Online News Association's annual convention in Washington, D.C., stated "Our largest driver of traffic is Matt Drudge."

On October 22, 2007, New York Times reporter Jim Rutenberg wrote that Republican and Democratic presidential candidates, including Hillary Clinton, were cooperating with Drudge and "working harder than ever to get favorable coverage for their candidates ... or unfavorable coverage of competitors ... onto the Drudge Report’s home page, knowing that television producers, radio talk show hosts and newspaper reporters view it as a bulletin board for the latest news and gossip." Rutenberg stated that Nielsen/NetRatings shows that the Drudge Report gets three million unique visitors over the course of a month, or approximately one percent of the population of the United States.

Income and lifestyle

A story by Business 2.0 magazine from April 2003 estimated that Drudge's website received $3,500 a day (almost 1.3 million a year) in advertising revenues. Subtracting his relatively minor server costs, the magazine estimated that The Drudge Report website grossed $800,000 a year. An article in The Miami Herald from September 2003 said Drudge estimated he earns $1.2 million a year from his website and radio show. During an April 30, 2004 appearance on C-SPAN, Drudge confirmed that he earns over $1 million. For many years, Drudge was based out of his one-bedroom apartment in Hollywood. Today, Drudge maintains the website from his two properties in Miami — his $1.4 million Mediterranean-style stucco house on Rivo Alto Island, and his $1-million-plus condominium in Miami's Four Seasons hotel. In updating the site, he reportedly monitors multiple television news channels and a number of websites on several computers in his home office. By early 2009, Drudge earned millions of dollars a year, travelled extensively (Israel, Las Vegas, Geneva), had moved to another property in Miami and become reclusive, communicating regularly only with a select group that included Rush Limbaugh, Ann Coulter, and Andrew Breitbart. In 2003 he named his one indulgence, apart from travel, as his Corvette.

Political views

Drudge, described as a conservative populist by The Daily Telegraph, champions himself as free from corporate influences.

In 2001, Drudge told the Miami New Times that:

Drudge pointed out differences between his political beliefs and those of the Republican party, arguing that his politics more accurately reflect libertarianism. In a 2005 interview with The Sunday Times Drudge described his politics:

Comments by journalists

Drudge has been called "the Walter Cronkite of his era" by Mark Halperin and John F. Harris, "an idiot with a modem" by Keith Olbermann, "the country's reigning mischief-maker" by Todd Purdum of The New York Times, and Michael Isikoff of Newsweek said "Drudge is a menace to honest, responsible journalism. And to the extent that he's read and people believe what they read, he's dangerous." According to Camille Paglia, he is "the kind of bold, entrepreneurial, free-wheeling, information-oriented outsider we need far more of in this country." David McClintick described him as, "a modern Tom Paine, a possible precursor to millions of town criers using the Internet to invade the turf of bigfoot journalists."