Olde English was formed by a group of students at Bard College, and was originally conceived by Ben Popik. While traveling in Europe during the summer of 2002, Popik chose the name for the group and began writing some of the early sketches. In the fall of 2002, Popik returned to Bard and held auditions for the group. Olde English currently consists of Adam Conover, Ben Popik, Raphael Bob-Waksberg, Dave Segal, and Caleb Bark, although several others have joined and left over the years.
Olde English has been producing videos on its website since 2002, at times posting an average of four new sketches a week. In 2004, Olde English released its first self-produced DVD, Gorilla Warfare. The group first gained popularity in 2003, when their video "Gym Class", was shown on Good Morning America. 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. The sketch, a parody of an internet phenomenon popularized by Noah Kalina and Jonathan Keller, rapidly gained popularity on YouTube, where it has been viewed over three million times. The video has since been featured on Good Morning America as well as a Mountain Dew ad campaign. On January 17, 2007, Olde English announced that its videos would be regularly featured on the comedy website Super Deluxe.
Olde English has performed live at the Chicago Sketch Comedy Festival (2005), the San Francisco Sketchfest (2005-07)and the U.S. Comedy Arts Festival (2007).
Olde English's "Free NYC Rap," a rap music video protesting the restrictions for independent New York City filmmakers that were proposed in Fall 2007, was nominated for a 2007 ECNY award.