Fail Blog
An online comedy and entertainment brand built around humorous failures, mishaps, workplace stories, and user-oriented internet culture.
Last updated August 22, 2026
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Overview
Fail Blog is a comedic online publishing brand launched in January 2008 and later incorporated into the Cheezburger network. Its original editorial identity centered on photographs and videos depicting accidents, mishaps, poor decisions, unsuccessful projects, and examples of people apparently doing an activity incorrectly. Posts were commonly labeled with short, highly reusable captions such as “fail,” “epic fail,” or “[activity] fail,” helping the site turn the idea of failure into a recognizable internet-comedy format. The site gained attention quickly during the late-2000s expansion of image-based blogs and user-generated internet culture. Pet Holdings Inc., the company behind the expanding Cheezburger network, acquired Fail Blog in 2008. Ben Huh, then the network’s chief executive, later associated the site’s growth with the broader public mood during the financial crisis, when the language of failure became especially visible in political and economic commentary. Fail Blog’s cultural reach was illustrated by the appearance of a “FAIL” sign during a 2008 United States Senate hearing involving former Treasury Secretary Henry Paulson and Federal Reserve Chairman Ben Bernanke. At its peak in the early 2010s, Fail Blog was one of the better-known humor sites in the expanding social-web ecosystem. It received two 2009 Webby Awards in humor-related categories and was discussed by major newspapers and magazines as a prominent example of online comedy. Commentators also credited the brand with helping popularize “fail” as a noun and exclamation in mainstream internet language. The brand operated or supported related properties and recurring formats, including Failbook, which focused on mishaps from Facebook, Ugliest Tattoos, and There, I Fixed It, a site or feature devoted to improvised and unsuccessful repairs. In 2016, the Cheezburger collection, including Fail Blog and its associated sub-brands, was sold to Literally Media, an Israeli-owned digital media company. Under its later editorial model, Fail Blog shifted emphasis from primarily captioned photographs and videos toward written accounts of real-life situations. Much of its contemporary material is sourced from Reddit or similar online communities and supplemented with introductions, commentary, and illustrative images. Common themes include difficult bosses, workplace disputes, customer-service conflicts, homeowners-association arguments, family drama, entitled behavior, and other everyday social failures. Fail Blog is therefore best understood as a digital media and comedy brand rather than a conventional consumer-product label. Its business model and public identity have depended on editorial aggregation, viral distribution, advertising-supported web publishing, and the continued circulation of recognizable “fail” formats across social platforms. The brand’s historical importance lies in its role in codifying a widely imitated form of internet humor and in helping make “fail” a durable part of popular online vocabulary.
History
Fail Blog began in January 2008 as a comedy website devoted to visual examples of failure. Its early posts generally consisted of photographs or videos accompanied by concise captions identifying the incident as a “fail,” “epic fail,” or a failure associated with a particular activity. The format was simple, highly legible, and well suited to sharing, which helped the site participate in the rapid growth of image-based humor and viral web publishing during the late 2000s. Pet Holdings Inc., the company assembling the Cheezburger network, acquired Fail Blog during 2008. The acquisition transformed the site from an independent blog into a permanent Cheezburger sub-brand. Its popularity grew as the concept of “fail” became useful not only for comedy but also for commentary on public mistakes, institutional incompetence, consumer experiences, and current events. A notable public reference occurred during a September 2008 United States Senate hearing, when a demonstrator held up a “FAIL” sign behind Henry Paulson and Ben Bernanke. The incident reflected the extent to which the term had moved from niche internet slang into broader political and cultural discourse. Fail Blog expanded its editorial footprint through related properties and themes. These included Failbook, focused on failures associated with Facebook; Ugliest Tattoos; and There, I Fixed It, which showcased improvised repairs and questionable technical solutions. The network structure allowed the brand to cover different varieties of visual humor while retaining the central idea that ordinary mistakes and bad solutions could be packaged as entertainment. The site reached a significant level of recognition by the early 2010s. In January 2010, it was reported to receive approximately 1.1 million unique visitors per month. It won two 2009 Webby Awards in People's Voice categories for Humor and Weird, and it was profiled or referenced by outlets including The Times, the Los Angeles Times, Time, and The New York Times. Media commentary frequently described Fail Blog as a leading online comedy destination and associated it with the mainstream adoption of “fail” as a noun and exclamation. The brand also experienced the legal and reputational risks of highly shareable user-oriented publishing. In July 2009, it posted a screenshot of a Guinness World Records webpage involving a record for people killed in a terrorist attack, alongside a link encouraging readers to break the record. Guinness threatened legal action, and the episode was subsequently reported by technology news organizations. The incident became one of the more notable controversies associated with the site, illustrating the difficulty of balancing provocative humor, editorial judgment, and third-party intellectual-property or reputational concerns. In April 2016, Literally Media acquired Cheezburger and its portfolio of websites, bringing Fail Blog under new ownership. In its later form, the site increasingly emphasized written real-life stories rather than only captioned images and videos. Its material commonly draws from Reddit and other online communities, with editorial introductions, commentary, and illustrative photographs added for presentation. Recurring subject areas include workplace conflicts, unreasonable bosses, customer-service disputes, homeowners-association disputes, family tensions, and entitled behavior. Fail Blog remains a digital entertainment brand whose importance is primarily cultural and editorial. It helped establish a repeatable grammar for internet humor based on labeling mistakes and mishaps, contributed to the popularization of “fail” terminology, and demonstrated how a narrowly defined comedic concept could become a scalable media property within a larger network.
- 2016
Acquisition by Literally Media
[1]Literally Media purchases Cheezburger and its associated sites, including Fail Blog.
- 2010
Reported monthly audience reaches 1.1 million unique visitors
[1]Contemporary reporting cites approximately 1.1 million unique visitors per month.
- 2009
Webby Award recognition
[1]Fail Blog wins two People's Voice Webby Awards in the Humor and Weird categories.
- 2008
Fail Blog launches
[1]The website begins publishing humorous photographs and videos centered on mistakes, mishaps, and unsuccessful behavior.
- 2008
Acquisition by Pet Holdings
[1]Pet Holdings Inc. acquires the site and integrates it into the Cheezburger network.
Products and positioning
A mass-market digital comedy brand focused on relatable mishaps, social absurdity, unsuccessful problem-solving, and stories of everyday incompetence or entitlement.
Digital comedy website · 2008
FAIL Blog
The core Fail Blog property publishes humorous material about mistakes, mishaps, incompetence, workplace conflict, family drama, customer-service disputes, and entitled behavior. Its earlier identity relied heavily on captioned photographs and videos, while its later editorial approach has placed greater emphasis on written real-life stories sourced from online communities and supplemented with commentary and illustrative media.
Social-media humor sub-brand
Failbook
A related Fail Blog property focused on humorous failures and awkward incidents associated with Facebook and social-media use. It extended the central “fail” concept into a specific online platform and formed part of the broader Cheezburger network of themed entertainment sites.
Improvised-repair humor site
There, I Fixed It
A related property built around improvised repairs, makeshift engineering, and questionable solutions. Its humor comes from the gap between a problem requiring a proper fix and an inventive but visibly inadequate workaround.
Themed humor website
Ugliest Tattoos
A related Cheezburger-era property presenting tattoos selected for their unusual, poorly executed, or otherwise humorous appearance. It applied the network's themed, image-led entertainment model to body-art content.
Controversies
2009
Guinness World Records legal threat
Fail Blog posted a screenshot of a Guinness World Records webpage concerning a terrorist-attack death record and included a link encouraging readers to break the record. Guinness threatened legal action, and the episode was reported by technology media. The incident raised concerns about the boundaries of provocative online humor and the use of third-party web material.
Brand decisions
2016
Transfer the brand to Literally MediaM&ABackground
Literally Media acquired Cheezburger and its collection of sub-sites and sub-brands.
Action taken
Fail Blog moved into the Literally Media portfolio.
Aftermath
The brand continued as part of a larger digital-media group and later emphasized real-life written stories alongside its established comedy formats.
2008
Integrate Fail Blog into the Cheezburger networkM&ABackground
Pet Holdings acquired Fail Blog while expanding a portfolio of online humor brands.
Action taken
The site became a permanent Cheezburger sub-brand rather than remaining an independent comedy blog.
Aftermath
The integration gave Fail Blog access to a larger network of related sites, formats, and audiences.
Sources2 sources
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