Matthew Drudge was raised in Takoma Park, Maryland, near Washington, D.C. His parents follow Reform Judaism. Both are Democrats who worked for the federal government, and he is their only child. His father, Robert Drudge, a former social worker who owns the reference site 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 says that he "failed his Bar Mitzvah", and graduated 341st out of a class of 355 from Northwood High School in 1984, giving himself, in his words, a "more than adequate curriculum vitae for a post at 7-Eleven".
In the 1980s, Drudge worked as a telemarketer for Time-Life Books.
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 e-Mail notes 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 published the reporting of then Newsweek Reporter Michael Issikoff, becoming the first media outlet to publish 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.
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 netted $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. In updating the site, he reportedly monitors multiple television news channels and a number of websites on several computers in his home office.
From June 1998 to November 1999, Drudge hosted a Saturday night television show called Drudge on the Fox News Channel. The show ended by joint consent. Drudge had refused to go on air, charging Fox News with censorship when the network prevented him from showing photos of surgery on Samuel Armas. Drudge, who is anti-abortion, 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 photo was not of an abortion but an emergency operation on the fetus for spina bifida. Fox News alleged breach of contract but, after Drudge issued an apology, Fox issued a statement calling the parting "amicable."
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 notice in the early 2000s by becoming a frequent 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. Lynn Samuels, for a time, served as Drudge's call screener.
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. It reached the New York Times Best Seller list. The book features a transcript of a Q&A session conducted at the National Press Club on June 2, 1998, which lays out Drudge's raison 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 said "Indeed, while Drudge Manifesto runs 247 pages ... Which leaves, in the end, 112 pages of new material, including nine pages of poetry." A review from the Columbia Journalism Review, said "By any standard, Drudge's book is padded." and "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 wrote 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."
In 2006, Time 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 says "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., said "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.
During the 2012 Republican presidential primaries, Drudge was described by some, including former presidential candidate Fred Thompson, as having a pro-Mitt Romney slant.
Drudge had a long relationship with Washington D.C. landscaper, David Cohen. Cohen confirmed the relationship to the New York Daily News. Drudge previously lived in Hollywood. As of 2007, he owns two properties in Miami – a $1.4 million Mediterranean-style stucco house on Rivo Alto Island, and a $1-million-plus condominium in Miami's Four Seasons hotel. By early 2009, Drudge earned millions of dollars a year, travelled extensively (Israel, Las Vegas, Geneva), moved to another property in Miami and had become reclusive. In 2003 he said his one indulgence, apart from travel, was his Corvette. He was listed on Out Magazine's Power List of the top 50 "list of gay men and women whose power and prestige is instrumental in influencing how we think about, and engage with, the world" in 2011, 2012, and 2013. Drudge specifically denied being homosexual in response to the Out Magazine article.
Drudge, described as a conservative populist by The Daily Telegraph, describes himself as free from corporate influences.
In 2001, Drudge told the Miami New Times that "I am a conservative. I'm very much pro-life. If you go down the list of what makes up a conservative, I'm there almost all the way."
In 1998, Drudge said that his politics are "libertarian except for drugs and abortion". In a 2005 interview with The Sunday Times Drudge described his politics "I'm not a right-wing Republican. I'm a conservative and want to pay less taxes. And I did vote Republican at the last election. But I'm more of a populist."
Drudge has been called "the Walter Cronkite of his era" by Mark Halperin and John F. Harris, and "the country's reigning mischief-maker" by Todd Purdum of The New York Times. 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."