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At a time when news organizations are struggling to grab the attention of audiences in a media‐saturated environment, social networking sites (SNS) have created novel opportunities for journalists to connect with followers online—raising questions about how types of social media use might be associated with forging greater connection with users. Just as satire has proven a potent force for attracting audiences to fake news TV programs, it’s reasonable to consider that humor might be an emerging tool for connection in social media spaces where journalists increasingly conduct their work. Through a content analysis of more than 22,000 tweets (or microblog posts), this study examines the extent to which the 430 most‐followed journalists on Twitter are using humor—and how such use is associated with other forms of engagement on Twitter. Findings indicate that a journalist’s use of humor is closely associated with sharing opinion and personal life details, and engaging in interpersonal discussion. Moreover, the use of humor is positively related to a journalist’s level of activity on Twitter, suggesting that journalists who become more accustomed to this social space are more apt to adopt its milieu of informality, conversation, and humor. Finally, journalists from less elite news organizations tend to use humor more frequently. These and other findings are discussed in light of challenges facing the journalism field as it negotiates questions of participation and professionalism in digital media spaces.