I don't know if it's my best but I'll tell you about the first time I ever smoked weed.
It was Myself, my buddy Leo and my mate Archer. It was the tenth grade. We were 16.
For the past couple of weeks Arch and I had been staying at Leo's house, it was in a nice estate area with a few parks. Just a good place to hang out. Well it was about 8 or 9pm and we were getting board after spending the day in Leo's room watching movies. Leo (who had smoked 2 or 3 times before) suggested that we pick up some weed and smoke it once his parents went to bed. (Neither me or Arch had smoked before.)
We agreed because ya know. We were 16. So Leo jumps on Facebook and messages his dealer, aka the kid who lived a few streets over, aka the kid who graduated 2 years earlier, aka Bradley, aka B-Rad.
(No joke. He actually goes by B-Rad as in Be Radical. But that's neither here nor there)
Anyway, Bradley was like "yeah sure, I just got some new inventory"
(Me and Arch were like "this guys a deadset fuckwit")
Leo,was like "see I told you guys he's the man, trust me, I've been doing this for ages" etc etc etc 16 years old.
So we spit some bull shit to Leo's parents and walk over to B-Rads place. It's a street or so away from Leo's house, right across from the park. The streetlight was flickering for some reason, fitting for my first ever drug deal.
Anyway we get to Bradley's driveway (it's a nice house, very WASP, very upper-middle-class-white people house) and there are two dudes standing either side of his garage. One had a baseball bat, the other had a chain. On the inside I was like, "what the fuck is this tony Montana shit" but on the outside I was ice cold, I put the big boy pants on. One of the "henchman" calls out to us, Leo says "yeah we're here to see Bradl- uhhh B-Rad"
Next thing I know the baseball bag gut knocks twice in the garage door. All of a sudden music erupts from behind the door, Darth Vader's Imperial March. You know the one. The garage door slowly rises to reveal two huge speakers sitting either side of a lazyboy. And sitting in his suburban throne, dressed in ablue Addidas track suit, looking like an eastern-European pimp, was B-Rad. Suffice it to say, my mid was fucking blown.
Leo, Arch and I pooled our money together and bought a gram of some shitty skank, took that shit home and blazed it on the playground across from Leo's house. So yeah pretty tame but still one of the funniest drug-related encounters I have had.
TL;DR My drug dealer as a kid was a suburban-archvillain with his own boss lair and goons.