Jack O’Brien launched Cracked.com in 2006, and was a driving force behind the site’s editorial and video content until he left in 2017 to become the Creative Director and Head of Comedy at HowStuffWorks. Under O’Brien’s leadership, Cracked grew into the most visited humor website on the internet, and one of the fastest growing brands in humor. In 2010, Cracked expanded its media reach with the New York Times Best Selling book, "You Might Be a Zombie and Other Bad News," on which O’Brien was the lead editor and art director. He co-created, co-wrote and oversaw “After Hours” (Winner of 2014 Webby for Best Writing, Web Series) and was the head writer and host of two of the fastest growing shows on the site; “The Spit Take,” a video series about hidden moments of brilliance and madness hiding on YouTube, as well as “The Cracked Podcast,” a weekly, hour long deep-dive into the most compelling ideas touched on by Cracked articles and videos.