Olympiad of Misguided Geeks at Worse Than Failure (abbr. OMGWTF) was a programming contest to “solve an incredibly simple problem using the most obscenely convoluted way imaginable”. It was started by Alex Papadimoulis because he wanted “to try out something new on [the] site.” Contestants for the OMGWTF contest were encouraged to focus on writing “clever code” (code which is unconventional and solves a problem that may or may not be solvable with conventional means) as opposed to “ugly code” (single letter variable names, no subroutines, and so on).

The goal of the first (and so far, only) contest was to “implement the logic for a four-function calculator.” It ran from 24 April 2007 to 14 May 2007 and received over 350 submissions which were then judged by popular technology bloggers Raymond Chen, Jeremy Zawodny and Joel Spolsky.

The winning entry was Stephen Oberholtzer’s “Buggy 4-Function Calculator”, which, according to judge Joel Spolsky “best exemplifies what real-world code looks like ... [it’s] not just bad code, [it’s] believable bad code.” In addition to “a High-Resolution JPEG of an Official Olympiad of Misguided Geeks at Worse Than Failure First Prize Trophy,” the winner received his “choice of a 15″ MacBook Pro or Sony VAIO VGN-SZ430N/B.”