He seems to fail every time: "In April 2011, Klayman filed a lawsuit against Facebook, accusing the social media website of "negligence" for not responding quickly enough to calls to take down an anti-Israel "Third Intifada" page and demanding $1 billion in damages. Facebook representatives responded that the suit was "without merit." In December 2012, the district court dismissed the complaint on 47 U.S.C. 230 grounds.

Also in 2011, Klayman represented Joseph Farah in his unsuccessful defamation lawsuit against Esquire magazine. In July 2011, Klayman represented Bradlee Dean in his unsuccessful defamation lawsuit against Rachel Maddow; Dean was eventually ordered to pay defendants' legal fees that totalled nearly $25,000.

In 2012, Klayman filed on behalf of a Florida resident an unsuccessful challenge to Barack Obama's placement on the primary ballot and claimed that the latter is not a natural-born citizen."