Winner: Google Assistant (with a rimshot)
Siri and Assistant both want to be more than programmed chatbots, so each has its own personality and a sense of humor. So, both tell jokes. Or, more specifically, both tell bad jokes. Siri and Assistant will both happily oblige to a variety of queries (including simply saying “joke”), but Assistant’s were a bit more engaging. Siri tended to stick to one-liners, whole Assistant’s jokes tended to be more question based. (Siri’s sense of humor is also a bit more iPhone-centric.) Additionally, you can say, “Tell me another,” or “One more” and Assistant will oblige, while Siri will need to be specifically told to tell another joke. – Michael Simon