​How come my AI don't bark when you come around?

I listened to the inimitable Dr. John last night singing his very wry song, "How come my dog don't bark when you come around?"

Now you say you ain't never met my wife, you ain't never seen her befo,'
Say you ain't been hangin' roun' my crib; well here's somethin' I wanna know...
I wanna know what in the worl' is goin' down,

How come my dog don't bark when you come around?     [more]

In a distracting moment of acute nerdiness, it occurred to me that this was a great example of the deep challenges of AI: Multiple levels of meaning and abstraction that require not only common sense understandings beyond the words and phrases, but the layers of conceptual, emotional and literary meanings, such as suspicion and irony.

Just parsing the literal meaning is the easy part.

• It is not so hard for our AI to understand the literal question.
• Does it understand the likely answer to to that question?
• Does it know what suspicions the likely answer leads to?
• ...who the parties are?
• ...and what actions those suspicions motivate?

Can Alexa or Siri or Watson figure that out? How, and how well. Now? or when? What other levels of understanding does AI face? Can that AI hunt?

(Of course these problems are well-known. This was just a flash of connection that amused me, before I returned to focusing on the performance.)