When: May 2010
Fox News
Anchor: Bill O'Reilly
Watch it here: O'Reilly tells guest he looks like a cocaine dealer

In the spring of 2010, Bill O'Reilly made the awkward, unfortunate mistake of telling a Columbia Ph.D he looked like someone who sold drugs. That person happened to be black. "Say you're a cocaine dealer—and you kind of look like one a little bit," O'Reilly said to a clean-shaved black man in a pinstripe suit. Marc Lamont Hill replied in somewhat bruising fashion, "As do you...you know, you actually look like a cocaine user." Nice job.