Do, really, immigration officers ask "What the hell where you doing X?" "Aren't those countries Islamic?" There are parts on this writing that are hard to believe, like they were written to sound like a novel, but I have never been on a situation like the one described, not even close.
I'm afraid so. While I still lived in the US (I'm American), my Malaysian wife lost her green card. As a result, she just had a stamp in her passport (this was the temporary green card) for ages, and each time we flew into NYC we were sent to the "back room" for further questioning.
The agents in front were often somewhat rude; in the back there was a sort of waiting room (with often 20 or so people in chairs) and a front desk where the agents would literary SHOUT at the people called up in front of them. It was not a private interview room (though presumably those were available as well). We were silently horrified during the 10 minutes or so they were shouting and badgering a cringing 60 year old Greek (I think?) man with poor English who apparently had something related to child support out of order in his documents.
There's something very hard to shake about the feeling you get when you are obliged to act polite & unconcerned to petty officials like these when you are inwardly seething with rage.
We left the US in 2006, and still go back on occasion (parents, friends, etc. are still there!), though the last time was now a few years ago. We still dread the immigration experience, though; it's likely to be fine (we don't make stupid mistakes about what we say, and we fake friendliness well), but it always feels like somehow, something will go wrong.
We've were once detained for 45 minutes or so at the English border as well, driving up from France -- we made the mistake of entering while pregnant without being prepared for their suspicion (NHS leeches!) -- but while it was frustrating to be stopped & questioned, they were impeccably polite and kind to us (though they did put a warning in my wife's passport without a word to us... we didn't notice until the next trip through the UK, when we were questioned about that).
Remember that the guy working the border post for the train from Montreal to New York is fairly unlikely to be particularly well traveled, and I'd imagine the vast majority of people they meet fit into a very small category of tourists and Canadians. A border officer working in LAX will have seen far more international travelers. Suspicion of Singapore and Malaysia as a whole doesn't really hold up when you get 500 people a day arriving from there.
I've had UK and Australian Customs officers be similarly incredulous over places I've visited. Honestly, those jobs don't seem to attract the "best and brightest". Nor attract those who even have a passing familiarity with geopolitics and geography. Sigh
Why would any border guard be incredulous over anyone visiting far away places? You'd expect border guards to be used to meeting foreigners. And there's lots of foreign parts in the world.
Why would anyone visit X? Because it's there. Because people live there. Because there are things to see. What other reason do you need?
Some of their questions are there to gauge your response, not get information, but I still have a hard time believing they would call him "a Jew" instead of a version of "Jewish".
