Dropout content is mainly composed of live play, such as Dimension 20, and improv comedy and panel shows like Game Changer and Make Some Noise.

In its earlier years operating as an advertising-based business under the name CollegeHumor, the company focused on sketch comedy and scripted content which was posted to their website (CollegeHumor.com) and later YouTube.

The CollegeHumor website featured daily original humor videos and articles created by its in-house writing and production team, in addition to user-submitted content.

Some popular series produced under the CollegeHumor brand include Jake and Amir, Hardly Working, Adam Ruins Everything, Hot Date, and Very Mary-Kate.

[4] The current CEO is Sam Reich, a performer and former Chief Creative Officer of CollegeHumor, who acquired the company in 2020 from IAC.

[15] In 2001, they added Jake Lodwick, a student at Rochester Institute of Technology, and Zach Klein, a friend of Van Veen's from Wake Forest.

[14] The group moved the company to San Diego briefly[14][17][16] before settling in New York City in 2004, where they set up shop in a 4,800 square-foot loft in TriBeCa.

[28] Under Electus Digital, Reich founded CH Media's offshoot production company Big Breakfast, and moved CollegeHumor's video team to Los Angeles.

[31][32] In December 2014, Fortune's Erin Griffith reported that IAC was considering selling CollegeHumor with the aim of finding a buyer who would "pay around $100 million" for the company.

According Griffith, this was part of a trend of comedy websites and other video outlets seeking to be sold after Disney acquired the Maker Studios YouTube channels for almost $1 billion.

However, Facebook never delivered the expected revenue which led to a pivot towards developing a subscription service "by mid- to late 2017" to "better monetize its audience".

[36] On January 8, 2020, it was announced that IAC was selling CH Media to its Chief Creative Officer, Sam Reich, resulting in the job loss of nearly all employees and staff.

[4][5] Reich said in 2024 that he had paid nothing for CH Media, as IAC's aggressive approach towards quickly selling the company had resulted in it receiving very few offers.

[6] The restructured company was reduced to seven people;[37] Brennan Lee Mulligan, Dungeon Master of the series Dimension 20, was the only creative left on the payroll.

[39] Knibbs commented that "Reich is beloved within the CollegeHumor community—WIRED spoke with more than a dozen former employees, and the praise was unanimously effusive, rare for someone who just laid a bunch of people off".

[40] Also that month, it was announced that Drawfee was to be spun off into an independent company, owned by creators who had previously lost their CH Media jobs.

'[43]In July 2022, PC Magazine commented that the current slate of shows still reflected the January 2020 reduction "to a skeleton team with far fewer resources and full-time staff to create original content.

In addition, the website hosted a large collection of user-submitted viral videos, encompassing home movies, bizarre sports highlights, sketches, and such.

[78] The half-hour comedy was written by and starred nine CollegeHumor editorial staff members (Ricky Van Veen, Jake Hurwitz, Amir Blumenfeld, Dan Gurewitch, Patrick Cassels, Sarah Schneider, Streeter Seidell, Sam Reich and Jeff Rubin), who played fictionalized versions of themselves.

[79] CollegeHumor.com posted original writing from its staff and users, including humorous essays, comics, interviews and weekly columns on sports, video games, college life, and dating.

Contributing writers to the site have included notable comedians Steve Hofstetter, Christian Finnegan, Brooks Wheelan, Paul Scheer, Amir Blumenfeld, and Judah Friedlander.

A comedy series in which four performers act out a newscast and read absurd or comedic text from a teleprompter, with points deducted each time they laugh or smile.

Special guest appearances have included Jewel, Michael Winslow, Ty Mitchell, Bob the Drag Queen, Tony Hawk, Giancarlo Esposito, and Eric Wareheim.