Artistic License: Occasionally. Of course, as a humor site, they aren't meant to be taken seriously in the first place. A particularly funny example, in one article mocking The British Empire, they had a picture of The Rhodes Colossus, with the caption "This is how they viewed themselves. Seriously." Trouble is, the cartoon was satirical - the whole point of it is taking the piss out of the Imperialist ambitions of Cecil Rhodes et al. Furthermore, it appeared in Punch, a joke magazine. Presumably the original publishers of the cartoon would find it as funny that their joke pages are being used seriously as Cracked would be if one of their Photoplasty images makes into some far-off history tablet.
Fake American: Despite being "America's Only Humor & Video Site," quite a few of their writers aren't American but will sometimes try to pretend they are—usually with Eagleland type 2 results.
Mean Character, Nice Actor: Dan O'Brien's writing persona does things that would terrify Charles Manson; Dan O'Brien himself is a somewhat awkward nerd who has a talent for beatboxin' Team Plasma and Kyurem, the last of the regular reader commentators uses the name A.E.Neuman.
Executive Meddling: What brought the mag down. Tabloid owner Dick Kulpa bought the mag, and as a cost-cutting measure, turned most artists' and writers' pays to flat-rate instead of by page. As a result, many veteran writers/artists left, such as Walter Brogan and John Severin. Kulpa was literally running the mag from his kitchen table, plastering it with tabloid-like covers, constantly delaying releases, and overall ruining the mag through his lack of experience.
Hey, It's That Guy!: Mad stalwart Don Martin crossed over in the 1990s after leaving Mad over a salary dispute, with Cracked making a big deal about stealing away one of their rival's most iconic cartoonists. He is hardly the only artist or writer to have worked at both magazines; long-standing Cracked artist John Severin also worked with Mad in its comic days. Also, one of the last new talents to join Cracked in the 1990s was Tom Richmond, who now draws a large amount of the Mad movie and TV parodies. Other Mad personnel who once worked with the rival include Jack Davis and Al Jaffee.
Bill Wray was a frequent contributor in the 80s. He later moved on to draw various comics for Dark Horse and Mad, and even did some work on The Ren & Stimpy Show.