How to make people uncomfortable without really trying

The other day this customer said something that was strikingly bizarre and therefore absurdly funny...
However, before I give you the money shot quote or any more adverbs, there's some background:
I should mention that this particular customer, who I'll refer to as Mr. Awkward, is strange enough as it is and manages to delicately balance being really nice and making me feel really uncomfortable. He's got these eyes... these freaky eyes that don't move from their locked position on your face (or you crotch, depending) no matter what nature of conversation you're having with him. He's one of those 50-something guys who looks hard as nails (nothing brokeback) but is super sweet, forcing me to question his sexuality and his motivation for certain conversations on more than one occasion.
His sexuality having nothing directly to do with his quote, I'll move on.

So it was a busy evening at The Wave, lots of customers and chaos abound. He steps up and impliments one of his classic "make people uncomfrotable" tactics: The long stare & The unnecessarily long thought-out answer to everyday meaningless questions. It's a classic.
Example:

Me: Hey, how are you?
Him: (Staring at me with intense concentration and a huge cheshire cat smile)...... I'm... (thinks about it) ... I'm GREAT, and how are you sir?
Me: Quite well, thank you
Him: (after a few seconds of thought and more staring)... Really? Are you really?
Me: um.. Yep!
Him: (ear-to-ear smile still plastered on face) Well that's good to hear
Me: Yes, isn't it? How about I get your movies and get you out of the store ASAP? Ok? Excellent.

It's great to have a genuine "how are you?" conversation as opposed to the constantly insincere repetative kind, but this man has no emotional (or financial, as far as I know) investment in my life, and he sees me like once a week, so what the fuck is his deal? Why is he so obscenely interested in how I'm REALLY doing? And why the fuck is he staring like that!? What the balls?

In the meantime, there is a young mother (actually, she looked about 19) holding her baby while waiting in line at the other register and Mr. Awkward turns to her, see's the baby and loudly and abruptly exclaims:

"Hey... nice baby"

Hey... nice baby. Think about hearing that... Imagine saying that to some woman you've never met before. Imagine some random guy saying that to you. What a way with words Mr. Awkward has, huh?

I can imagine him saying all kinds of blunt, awkward things.

Mr. Awkward at a strip club: "Hey... nice vagina"
Mr. Awkward at a hospital: "Hey... nice tumor"
Mr. Awkward at a funeral: "Hey... nice casket"
Mr. Awkward at a wedding: "Hey... nice wife"
and so forth.

So there's my one quote, elongated into several paragraphs.

-Jordan