"One hand for the ship, one hand for yourself." I.E. one hand to do the ship's work, one to hold on to the railing so you don't fall off. Two hands for the ship, and you're not looking out for yourself. Two hands for yourself, and why would the ship want to keep you?
So we're not actually any farther ahead. Personally, the advice I'd probably give a person in this situation: ask a lawyer from the area. Compared to a FAANG salary, it's a cheap investment. I might also recommend paying cash, and not giving a real name.
You're right about plenty of managers being jerks, but on the other hand, do you really want to work for someone who would freak out if they knew you did dumb stuff when you were a kid?
Also, you're probably not going to get a decent lawyer to agree to aliases, and the last thing you want to do is lie to your own lawyer. That's how you get them to quickly stop counseling you. Your lawyer and your doctor are the two people you want to be 100% transparently honest with so that they can accurately advise you.
For example, for jobs that require a security clearance, it's probably best to just divulge everything that won't get you arrested. At a job fair, I met a recruiter who hired for top secret clearance jobs. I asked him how they could possibly find people who had never had smoked weed, and he said they were primary concerned with recency and frequency.
Honesty when filling out your form SF-86. Are you gonna lie about being contacted by a foreign agent in the future just like you lied about smoking a couple puffs in high school? Lie on the SF-86 and get caught and its instant permanent deny.
Blackmail opportunity where if you have a current or likely future addiction a foreign agent could provide you with money or drugs or silence in exchange for info. So a couple puffs in high school, who cares, on the other hand stripping copper to pay for meth last week is instant deny. Same blackmail issue for credit report issues. In the really old days it was the same thing for non-hetrosexual people, if they figure you could get blackmailed then no clearance.
There's a lot of hand wavy but assuming you're functional in the sense of not being high at the interview while also not being the most financially insolvent person in your future department, the only real way to fail a mere S or even a TS is to lie on your SF-86 when you apply. The vetters have a rough subjective job so they really like finding an objective factual falsehood like a misdemeanor possession or similar, because then they can take it easy and stamp deny.
They give the contracted firm their set of criteria, then the other firm comes back with a pass/fail.
OTOH, if you lied to me and I found out you were busted for a tiny amount of weed, I'm going to burn your application. Not because of the arrest - again, I don't even care about that - but because you've lied to me. At that point I'm not going to trust anything else you tell me. Are you also going to cover your mistakes at work and hope no one notices?
Every company is different, so I'm only speaking for myself and not the industry as a whole. But I would infinitely prefer that a candidate tell me this stuff up front than to try and hide it from me. And frankly, if you got arrested for some very cool reason ("I was part of a protest against a white supremacist march!"), it could quite possibly tip the hiring decision in your favor!