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The paper reports on the study that developed a classification of humorous interactions with intelligent personal assistants (IPAs) and applied the classification to compare four IPAs, Apple Siri, Google Assistant, Amazon Alexa and Microsoft Cortana, on their humor performance. The study relied on volunteer participants recruited through traditional academic channels (e.g. mailing lists) as well as Amazon Mechanical Turk (AMT). While AMT and non‐AMT participants differed on some demographic characteristics, their overall ratings of IPA humor were not significantly different and were analyzed jointly using descriptive and inferential statistics. The results revealed that Apple Siri and Google Assistant received higher average ratings on humorous IPA responses compared to Amazon Alexa and Microsoft Cortana. IPA responses to joke requests were judged as being funnier than IPA responses to questions related to the IPA's personality, rhetorical statements and other humor types. Consistent with previous studies on humor, our findings did not demonstrate strong relationships between select user demographics (age, gender and humor style) and their ratings of humorous IPA responses. [ABSTRACT FROM AUTHOR]