He published the Internet humor site Cruel.com and is the copublisher of the community weblog SportsFilter and the Drudge Retort, a liberal alternative to the Drudge Report that he edits with television writer Jonathan Bourne. He has also been a contributor to Suck.com and previously authored a syndicated question-and-answer column called "Ask Ed Brice."
When Matt Drudge failed to register drudge.com for his now 10 year old news and gossip website drudgereport.com, Cadenhead registered drudge.com and started the Drudge Retort as a liberal alternative to the Drudge Report. Both conservative and liberal bloggers utilize the open forum format encouraged by Cadenhead on the Drudge Retort.
In December 2005, Cadenhead again achieved significant blog and media coverage by highlighting that Wikipedia co-founder Jimmy Wales had edited his own Wikipedia article repeatedly, which Wales admitted was "in poor taste."
In June 2008, the Associated Press filed seven DMCA takedown requests against Cadenhead for stories published by users on the Drudge Retort reproducing from 39 to 79 words of AP articles. The action sparked a backlash among bloggers towards the news organization and a debate about what constitutes fair use when bloggers link and excerpt articles. "If The A.P. has concerns that go all the way down to one or two sentences of quoting, they need to tell people what they think is legal and where the boundaries are," Cadenhead told the New York Times.