[5] Maddox attended the University of Utah, but left without a degree after accumulating 122 credit hours, having already secured employment as a computer programmer.
[11] He was also working on a reality television show for Spike TV titled Manformation with Thom Beers and Dax Herrera until the project was shelved in 2011.
[14][15] Maddox has also performed in the Upright Citizens Brigade Theatre and in the horror film Ooga Booga as the character Skeez.
Launched in 1997 without any high expectations, the website was primarily a personal homepage for Maddox to host his writings while working as a telemarketer for a small software company.
He gave the list to several people on EFnet's Internet Relay Chat channel #coders, and the positive response led him to create the website.
[28] On July 15, 2009, Xmission.com, an ISP which hosts The Best Page in the Universe among other Utah clients, had an Alexa rank of about 16,000, declining to 77,000 by June 2017 and almost 300,000 by November 2021.
Maddox also stated that the sparsity protested the many websites that contained "fancy HTML" but lacked substantial content.
[26] The site uses large, light-colored text on a black background to, in the stated opinion of Maddox, reduce strain on the eyes.
[26] Images include elderly people being fired into the Sun, hippies being killed, and Maddox's testicles drawn larger than basketballs.
When posting his replies he breaks the e-mail down and ridicules points which use fallacious logic and also corrects grammatical or orthographical errors.
[35] In 2014, Maddox created a weekly podcast titled The Biggest Problem in the Universe, co-hosted by Dax Herrera under the pseudonym "Dick Masterson".
[39][40] In 2017, Maddox filed a $372 million harassment lawsuit with the New York Supreme Court against Herrera, individuals at Patreon, and Weber Shandwick copywriter Asterios Kokkinos who made guest appearances on The Biggest Problem in the Universe and The Dick Show.
They cited an album by Kokkinos and a billboard contest by Herrera, which both attempted to mock Maddox, along with targeted ads on Facebook and Reddit.