Olde English was formed by a group of students at Bard College, and was originally conceived by Ben Popik.

[3] By 2010, Olde English consisted of Adam Conover, Ben Popik, Raphael Bob-Waksberg, Dave Segal, and Caleb Bark, although several others had joined and left over the years.

[citation needed] In 2006, the group released a video titled "One Picture Every Day", starring Ben Popik and featuring an original song by former member Jesse Novak.

[9] On January 17, 2007, Olde English announced that its videos would be regularly featured on the comedy website Super Deluxe.

[10] Olde English performed live at the Chicago Sketch Comedy Festival (2005),[11] the San Francisco Sketchfest (2005–2007)[12] and the U.S.