Maddox started The Best Page in the Universe in 1997. The majority of the content is satirical: it focuses on society, pop culture and masculinity, enthusiastically endorses chauvinism, and expresses dislike towards children, senior citizens, women's rights activists, vegetarians, environmentalists, hippies, celebrities, personalities, George W. Bush, Mac users, goths and jocks. Many of Maddox's articles include illustrations of elderly people being fired to the Sun, hippies being killed, and Maddox's testicles (drawn larger than basketballs). The site also criticizes hate mail the website has generated, breaking the e-mails down and ridiculing fallacious logic and writing errors. Maddox reported in 2006 that the site's online store earned enough for him to "stay above water."

Maddox is reported to have worked as a programmer for a telemarketing company until 2004. On May 9, 2006, Maddox, Tucker Max, and RudiusMedia blogger, DrunkasaurusRex, premiered a two-hour test show live on Maxim Radio on Sirius Satellite Radio. On June 6, 2006, Maddox appeared at the San Diego Comic Con with his comic book, The Best Comic in the Universe.

Maddox's first book, The Alphabet of Manliness, was published in 2006 and reached number one on the Amazon.com sales chart. The book is illustrated and has a chapter-length entry for each letter in the English alphabet regarding a "manly" topic (for example, N is for Norris, Chuck). Maddox announced in 2010 that he is writing another book in which he will critique children's artwork. The book is inspired by two articles on the site.

In 2010 he appeared on Bullshit!'s eighth season episode "Old People" and started his own web series, The Best Show in the Universe, on YouTube.