8. Google Calendar's Feeling Lucky Button

Year: 2008

Those who created an event on Google Calendar discovered a new "Feeling Lucky" option, which supposedly set users up on a date with any of the following celebrities: Jessica Alba, Pamela Anderson, Paris Hilton, Britney Spears, Anna Kournika, Matt Damon, George Bush, and even animated characters Eric Cartman and Lois Griffin. Seriously.