1966 – He was born on the 27th day of October this year in Takoma Park, Maryland near Washington D.C.
1984 – He graduated 341st out of a class of 355 from Northwood High School in this year. 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.
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.
1996 – His website gained in popularity in the late 1990s after a number of reports in which he beat the mainstream media by reporting first. He first received national attention in this year when he broke the news that Jack Kemp would be Republican Bob Dole's running mate in the 1996 presidential election.
1998 – He is best known and attracted national attention when it was the first to break the news of a relationship between Monica Lewinsky a White House intern and President Clinton. He also hosted a short-lived Saturday night television show called Drudge on the Fox News Channel until 1999.
2000 – He wrote a book titled “Drudge Manifesto”.
2004 – In one of his appearance on C-SPAN, Drudge confirmed that he has broken the seven-figure mark; after he was reported in an article in The Miami Herald from September 2003 said he earns approximately $1.2 million a year from his website and radio show.
2005 - In August of this year, he reported that Small Business Computing showed "rising star" Soledad O'Brien pictured with Drudge Report on her computer screen.
2006 – The TIME Magazine named Drudge one of the 100 most influential people in the world, and ABC News concluded that the Drudge Report sets the tone for national political coverage. For many years, he was based out of his apartment in Hollywood. Today, Drudge maintains the website from his condominium in Miami, Florida.
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