Occasionally, Drudge authors news stories himself based on tips. The Report originated in 1996 as a weekly subscriber-based email dispatch. It was most famous for being the first news source to break the Monica Lewinsky scandal to the public after Newsweek decided not to publish the story.

The Drudge Report started as a gossip column focusing on Hollywood and Washington, D.C. Matt Drudge began the email-based newsletter called Report from an apartment in Hollywood, California, using his connections with industry and media insiders to break stories, sometimes before they hit the mainstream media. Drudge maintains the website from his home in Miami Beach, Florida, with help from Andrew Breitbart, who assists in story selection and headline writing. Breitbart, who describes himself as "Matt Drudge’s bitch", works the afternoon shift at the Drudge Report, as well as running his own website (breitbart.com), and another website (BigHollywood.com) providing a conservative support system for people in the Los Angeles entertainment industry.

Drudge, who began his website in 1997 as a supplement to his $10/year email newsletter, 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 made national waves when he broke the news that Newsweek magazine had information on an inappropriate relationship between "a White House intern" and President Bill Clinton (the Monica Lewinsky scandal), but was withholding publication. After Drudge's report, Newsweek published the story.

The Drudge Report site consists mainly of selected hyperlinks to news websites all over the world, each link carrying a headline written by Drudge or his editors. The linked stories are generally hosted on the external websites of mainstream media outlets. It occasionally includes stories written by Drudge — usually two or three paragraphs in length. They generally concern a story about to be published in a major magazine or newspaper. Drudge occasionally publishes Nielsen, Arbitron, or BookScan ratings, or early election exit polls that are otherwise not made available to the public.

The site carries advertisements that generate the site's revenue. The Drudge Report's advertising is sold by Vienna, Virginia-based ad firm Intermarkets.

In April, 2009, Associated Press announced that it would be examining the fair use doctrine used by sites like Google and Drudge Report to justify the use of AP content without payment.

On May 4, 2009, the US Attorney General's office issued a warning to employees in Massachusetts not to visit the Drudge Report and other sites because of malicious code contained in some of the advertising on the website. In March, 2010, antivirus company Avast! warned that advertising at the Drudge Report, New York Times, Yahoo, Google, MySpace and other sites carried malware that could infect computers. "The most compromised ad delivery platforms were Yield Manager and Fimserve, but a number of smaller ad systems, including Myspace, were also found to be delivering malware on a lesser scale, Avast Virus Labs said."

The Drudge Report Web site has experienced very few changes since its 1997 debut, and remains entirely written in HTML with a mostly monochromatic color scheme of black boldface Courier New text on a plain white background. The Drudge Report was described by Cheryl Woodard, co-founder of PC, Macworld, PC World and Publish magazines, as "a big, haphazard mishmash of links and photos" and by Dan Rahmel as "popular despite a plain appearance". The Report website is simple and, according to Paul Armstrong of webwithoutwords.com, retro in feel. Jason Fried of 37signals.com calls it "one of the best designed sites on the web." It consists of a banner headline and a number of other selected headlines in three columns in monospaced font. Most link to an outside source, usually the online edition of a newspaper, which hosts the story. When no such source is available, either because the story is 'developing' with little known details at the moment or is an exclusive scoop, a special page is created on the Drudge Report servers which contain text and possibly images.

There are different importance levels a story could appear as on the site, the rating of which relies on Matt Drudge's editorial discretion. The Report almost always holds one major story above the logo, usually just one sentence hyperlinked to the most important story of the day. Other stories surrounding the main headline can be found in the upper left hand side of the page and link to more specific articles dealing with aspects of the headline story. The standard story, either the headline or links below the logo, are written in black. The stories Drudge considers most important are in red, all under a single major headline in large, bold type. For especially important breaking stories, especially if still emerging, Drudge places art of a flashing red light on the screen.

Although the site initially featured very few images, it is now usually illustrated with five or six photographs. Generally the images, like the linked headlines, are hotlinked from other news agencies' servers.