CollegeHumor was founded in 1999 by Josh Abramson and Ricky Van Veen as a website for college humor content. The site grew into one of the most popular comedy websites of the early internet era, known for original videos, articles, and viral content.
IAC/InterActiveCorp acquired CollegeHumor in 2006. Under IAC ownership, CollegeHumor expanded its video production and became a significant digital media company.
CollegeHumor launched Dropout in 2018 as a subscription streaming service, creating a paid platform for original content not available for free. Dropout featured original series including Game Changer (a comedy game show hosted by Sam Reich), Dimension 20 (a Dungeons and Dragons actual play show), and Um, Actually (a trivia show about nerdy topics).
In early 2020, IAC announced it was shutting down CollegeHumor's operations, laying off most of the staff. Sam Reich, who had been CollegeHumor's Chief Creative Officer, negotiated a management buyout of the company, acquiring the CollegeHumor and Dropout brands from IAC.
Under Reich's ownership, CollegeHumor Media rebuilt its team and refocused on Dropout as its primary business. The company shifted its strategy to prioritize the subscription streaming service over free ad-supported content.
Dropout grew significantly during the COVID-19 pandemic as audiences sought streaming entertainment at home. The service's original programming, particularly Dimension 20 and Game Changer, developed loyal followings.
By 2024, Dropout had grown to become one of the most successful independent subscription streaming services, with a dedicated subscriber base and a reputation for high-quality original comedy content. The company has continued to expand its content library with new series and formats.