I was born in 1976 in the beach town of Santa Cruz, California. I mention that to give a little frame of reference on which games were of my era, and for the fact that Santa Cruz was and still is mostly known for the Beach Boardwalk (if you've seen the classic horror flick Lost Boys you've seen the Boardwalk). Besides the rides at the Boardwalk it also has a large casino, maybe it was an actual casino back in the day (it's been there since the turn of the 20th century), during my time it's only ever been a large arcade.
I had the best grandmother in the world (yes, even better than yours). She would take me down to the Boardwalk more often than I deserved, we'd visit the rides often, but I think she preferred it when I spent time in the casino as it meant she didn't have to chase after me quite as much and could take it easier. If memory serves there were around 40-40 pinball machines in the casino at that time. I did enjoy some of the video game style arcade games, but the large majority of the quarters she never stopped giving me went into those pinball machines. The games I remember most from that era were all Williams machines, some favorites I'd play were Comet and Cyclone, Space Shuttle, Taxi and Pinbot. Comet and Cyclone were favorites back then as the themes matched up perfectly with the environment, playing them at an amusement park.
For years to follow, anytime the family would be at a pizza parlor, an arcade, or a business that had a pinball machine, that's where you'd find me. I specifically remember wanting to go to a particular pizza parlor not because they had the best pizza, but because they had Theater of Magic and Twilight Zone. The sandwich shop down the street had Fish Tales, OG Medieval Madness, Taxi, and Whirlwind. I spent many an afternoon in the baseball card shop playing their Jurassic Park machine.
In high school I finally fell in love with the game I'd never stop thinking about, the first one I got really, really good at, my initials filling all the spots on the machine, that game being FunHouse. I enjoyed the hell out of that game, fortunately I had a friend who enjoyed playing just as much, at least once a week we'd spend an entire afternoon and evening playing off of just a couple dollars, I think the people working at that pizza place got very sick of seeing us (they had unlimited refills on soda too which we took advantage of).
While going to community college I had a job working at a stereo shop, loads of fun as we always had the cool new toys, but it didn't pay well at all, and I was a broke college student. We had several regular customers that would come in just to see what cool new stuff we had, and would hang out sometimes and chat us up. There was one guy with whom I somehow got on the subject of pinball. I had no idea what he did for a living and he played it cool, not letting on that he was about to give me an awesome surprise. A few days later he comes in with this double bagged paper bag and hands it to me. It's heavy as hell, and filled with tokens for the casino at the Boardwalk, literally hundreds of dollars worth. Turns out he's a mechanic there and tells me that once I've gone through that bag he'd hook me up with more (and he did!). Besides the obvious jackpot of thousands of free pinball games, this served another purpose as well. Back to that broke college student thing, my poor girlfriend was hardly ever taken out on proper dates, no longer, ha ha our new regular date spot was at the pinball tables!
Had to grow up eventually, become an adult with a real job, get married, buy a house, pinball took a major back seat and for years I didn't touch a single machine. Got a little settled and had the idea that maybe I could actually own a machine myself. FunHouse was the first that came to mind. Long story short though, I am dangerous with even simple tools, and the thought of having to fix something that broke meant I was steered towards a brand new machine. Being a fan of the HBO series The Sopranos (wife enjoyed the show too, so that helped convince her, and no, didn't end up with the pinball playiing girlfriend), that's what was settled on.
Sopranos was our only game for the past 15 years until just a few months ago when I finally worked up my courage to grab a FunHouse. I look at it even when it's turned off and need to pinch myself, still can't believe it's mine! Seeing that my Sopranos hasn't lost any of it's value, I've convinced my wife that while pinball machines aren't really an investment, they aren't a waste of money, and they do hold their value. She's given me the okay to pick up a couple more if I find the right game. I'm hoping someday to find a good example of Comet or Cyclone...