When my father got the Tandy 1000, he picked up Lode Runner to go with the system as it was something we'd been watching the demo for at the local Radio Shack (but couldn't play because they had a damaged disk..)
It wasn't too much later that my father picked up F-15 Strike Eagle. That particular title, as primitive as it was, got both my father and I hooked on simulators. We'd both end up playing a large chunk of Microprose's simulations through the 80s and early 90s, and some of the others out there such as Gato, Silent Mission, and Falcon.
Of course, in 1990 I ended up getting myself addicted to the Wing Commander series. That would much much later get me into Freelancer and eventually Elite Dangerous.
More arcadey but still quite fun were the Ace Combat titles. I was introduced to that one with Ace Combat 4 on the PS2 and stayed with the series since.
Oddly, I think the simulator my father and I put the most time into was Sid Meier's Pirates!, which was a Carribean age of piracy simulator. We had to have put thousands of hours into that over the years, including even crashing the game multiple times by overflowing the memory space for storing the goods, ships, etc that you possess.
I would have gone into the Air Force, but the ear damage I had from shortly after my birth would have disqualified me. The road not taken, huh?