Once any content is published it is subjected to public scrutiny, and tort actions may be brought by people allegedly offended by it. In most of the western world, there are no prior administrative restraints on freedom of speech, but courts can analyze complaints about various forms of expression and, in cases where the content is deemed abusive, award financial compensation to the victim. Naturally, humorous content is not excluded from this principle, and humorists can therefore face lawsuits. The present study researched all competent courts in Brazil where electronic records were available for the period 1997–2014 in order to present an overview of such cases, focusing on the identity of the claimants and the success of their lawsuits. Analysis of these data allowed some trends and inconsistencies in how Brazilian judges deal with cases involving humor to be identified. The first observation is that courts tend to favor humor that is closer to journalistic comment, i. e., humorous pieces relating to subjects of public interest. Humor, however, is not and cannot be limited to this particular type of humor. The second observation is that many judges punish humor that in their view seems to be “exaggerated,” disregarding the fact that exaggeration and unreasonableness are trademarks of humor. Thus, conservative and highly personal positions on the part of judges create an environment of uncertainty surrounding cases involving humor and freedom of speech. It is suggested that better attention to precedents set by Brazilian Higher Courts and a degree of common sense (including a sense of humor) on the part of the judiciary would help overcome judicial bias against humorists.