[6] In early 2005, its owner Dick Kulpa sold the magazine to a group of investors who announced plans to revive a print version of Cracked with a new editorial focus and redesign.

[4] The site fit well within Demand Media's network, with Jack O'Brien noting "They understand the web, and they made us nail down a voice".

[14] The editorial staff includes original editor-in-chief Jack O'Brien, Jason Pargin (under his pen name, David Wong), who was added as an associate editor later in 2006, and Oren Katzeff, who became Cracked.com's general manager in November 2007 after running business development for Yahoo Media Group.

[4][5][14] Writer Daniel O'Brien was questioned by the FBI and United States Secret Service after writing an article titled "How to Kidnap the President's Daughter".

[24] In June 2017, Jack O'Brien stepped down from his position as editor-in-chief and left Cracked to build up the new comedy podcasting division at HowStuffWorks.

On December 4, 2017, E. W. Scripps laid off 25 staff members from the website, including Daniel O'Brien, Cody Johnston, and the entire video team, in an effort to cut costs.

[34] Afterward, Brockway and fellow longtime Cracked writer Sean "Seanbaby" Reiley then co-founded their own comedy website, 1900HotDog.com.

[36][37][38] The Cracked "front page" formerly contained columns by a staff of regular contributors, including Sean "Seanbaby" Reiley, Daniel O'Brien, Robert Brockway, Cody Johnston, Soren Bowie, Chris Bucholz, host and writer of the web series Hate by Numbers Wayne Gladstone, John Cheese, Christina Hsu, and Michael Swaim, head writer and performer of the sketch comedy group "Those Aren't Muskets!".

The site also hosted Pointless Waste of Time, Pargin's old forum, which contained a writer's workshop, a section for readers to submit content for the Photoplasty and Pictofacts contests, and a template for generating small, one-shot articles called "Quick Fixes," along with general and specific discussion threads on a variety of topics.

[14] Cracked became known for its popular listicles, which include titles like "The 6 Most Insane People To Ever Run For President" and "7 Basic Things You Won't Believe You're All Doing Wrong".

[18][54] For example, Ratatouille's description reads "Remy the rat is obsessed with good food, and he has learned to cook by watching television in the same way that Jackie Chan fans have all become Kung-Fu masters.

Remy stumbles upon an unsuspecting janitor working in a Parisian restaurant and figures out how to tap into his central nervous system, controlling his every movement".

[21][58] As part of the marketing campaign, Cracked encouraged fans to post pictures of themselves alongside the book with 50-word captions.

One noteworthy example of criticism came from Ashley Mangtani, as he wrote in his October 24 2021 piece on Medium, titled "The Downfall Of Cracked.com & The Cancellation Of The Once Famous Cracked Podcast."

Mangtani concluded that: "The bottom line is simple, Cracked were bought by a company that wanted nothing more than to break into the digital media market.