Here’s a few lists by generation.
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#1 Youthful discretions, heavy on my college years where I spent hours playing at the Texas Tech Student Union.

Mata Hari - first pin I really knew all the shots and code. I never went infinite, but could usually crack a free game 1 out of 3 or 4 times.
Black Knight - mesmerizing. Magnasave was like the hand of God printing quarters
Mr. and Ms. Pac-man - the game I learned to beat. 1 quarter, and I could play as long as I wanted.
Spectrum - 9 out 10 players had no idea how this game worked. Super, super fun once you figured out the rules. Still one of the most unique games, ever
Eight Ball Deluxe - best shots and theme of this era

runners up. Haunted House. 3 levels! 8 flippers! Spooky music! Absolute classic. Black Hole

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#2 Pinball collection and restoration v1.0 - the WPC glory days

MM - may STILL be the best game ever designed. Hilarious, approachable, mesmerizing
MB - Gomez masterpiece. Probably the best game for newbies ever done. Super-easy to approach, rewarding progression, and great sound package
CV - Incredible theme with fantastic art package. The DMD reflected in the field of play + the neon ramp + circus master and his magnetic personality. John Popadiuk master symphony.
ToM - Best “World under Glass” of this age. So thematically perfect. The theme itself was so understandable, the shots and modes were intuitive. Magic is still one of the all time best Pinball genres, and this is the best of the best.
LOTR - the only non WPC game of this era. The first Stern to rival Williams. Jaw dropping accuracy to the theme, with a 100% serious tone that does true justice to some of the greatest movies ever made. The only game I still own from this era I still own.

runnerup: IJtPA: so close to making this list. Might replace CV here. RFM: P2K, oh, what could have been! Utterly unique, and still one of the most hilarious games ever made, “here, take this dress!”

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#3 Pinball renaissance (v2.0 for me at least, back into the hobby today)

JP - shows how far pinball has come from the WPC days. stunning depth, and crazy varied shots. Add the movie code, and you have the complete package. My currently most-played pin
JJP GnR - nothing, NOTHING, touches this for a pinball experience. Really feels like you’re part of the concert, wailing away. The songs modes are utterly unique and different, and the light shows are untouched by anything ever made. Really, the future of pinball light and sound. THIS pinball shows what you get with full access to “assets” and the enthusiastic support of the rights owners.
GZ - deserving of the #1 overall ranking. The complete package, with insane toys, ramps, mechs, etc. Super-campy retro assets that make this a total blast to play.
Rush - I can’t be objective here. I’ve been the proto-Rush-nerd since 2112 was released in 1976. My favorite band meets pinball, and they didn’t screw it up! Great song selection, deep rules, and the special Rush humor combine to make my life complete. Thank you Alex, Geddy, and Stern
LOTR - still holds up, 20 years later.

runners up: The Hobbit (most especially with LOTR in the collection), Maiden