Curl, who served as morning shift editor, left the site in 2014 and, with Drudge's blessing, in January 2015 launched his own aggregator Right Read, for The Washington Times. In 2011, he added to the staff Charles Hurt, most recently the Washington bureau chief of the New York Post and a columnist for The Washington Times. In 2010, Drudge added former Washington Times columnist Joseph Curl to the Drudge Report staff.

John Ziegler has said that Drudge blocked Breitbart from posting content critical of Barack Obama during the 2008 campaign for the US presidency. Breitbart, who described himself as 'Matt Drudge's bitch', worked the afternoon shift at the Drudge Report, at the same time as running his own website, Breitbart News, which provided a conservative perspective for people in the Los Angeles entertainment industry. His first assistant was Andrew Breitbart. In its early days Drudge maintained the website from his home in Miami Beach, Florida, with help from assistants in story selection and headline writing. Matt Drudge began the email-based newsletter from an apartment in Hollywood, California, using his connections with industry and media insiders to break stories, sometimes before they hit the mainstream media.

The Drudge Report started in 1995 as a gossip column focusing on Hollywood and Washington, D.C. It was the first news source to break the Clinton–Lewinsky scandal to the public, after Newsweek decided to 'kill the story'. The Drudge Report originated in 1995 as a weekly subscriber-based email dispatch. The site consists mainly of links to news stories from other outlets about politics, entertainment, and current events it also has links to many columnists. The site was generally regarded as a conservative publication, though its ownership and political leanings have been questioned following business model changes in mid-to-late 2019. The Drudge Report (stylized as DRUDGE REPORT) is a U.S.-based news aggregation website founded by Matt Drudge, and run with the help of Charles Hurt and Daniel Halper.

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