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Deadline was founded by Nikki Finke, who began writing an LA Weekly column series called Deadline Hollywood in June 2002. She began the Deadline Hollywood Daily (DHD) blog in March 2006 as an online version of her column. She officially launched it as an entertainment trade website in 2006. The site became one of Hollywood's most followed websites by 2009.
In 2009, Finke sold Deadline to Penske Media Corporation (then Mail.com Media) for a low seven-figure sum. Finke was also given a five-year-plus employment contract reported by the Los Angeles Times as worth "millions of dollars," as well as part of the site's revenue. In September 2009, the URL was changed to Deadline.com and the site's name to Deadline Hollywood. The publication expanded to New York in 2010 with the hiring of Variety reporter Mike Fleming Jr. as the new Deadline New York editor,Financial Times editor Tim Adler to lead Deadline London, and Nellie Andreeva for the site's television coverage as "co-editors-in-chief, TV". Finke remained the editor of Deadline Hollywood until 2013.
In November 2013, Finke left Deadline after a year-long disagreement between herself and Penske, who had bought Variety, a competing trade magazine and website.
In first quarter of 2020, the website deadline.com was one of the most popular and reliable sources in different language versions of Wikipedia.