Okay, this sounds fun.
I think my top five, in no particular order, would be:
Lords of Vegas - I am shocked this is not in the top 500. This game really should have the mass market success of things like Ticket to Ride, Catan, and Wingspan. It’s easy to explain and play, you can be easygoing or cutthroat, and it has that thrill of the dice rolling both for gambling at an opponent’s casino, or when reorganizing trying to improve your control or take over a rival casino. You get some great highs when that longshot roll goes in a player’s favor, that even their opponents can’t help but cheer. I can only imagine the low rank is due to issues with Lone Shark Games, as there are some pretty interesting threads about their customer service.
Sheriff of Nottingham - I feel like this had to have been within the top 500 at some point, as it was a really hot item for a bit. Another one that just generates high points as players sneak a bunch of contraband past the sheriff, or conversely, the sheriff catches a bunch. Always good for some laughs.
Vampire the Masquerade: Vendetta - This game is horribly imbalanced once all players are familiar with the various clans, meaning it is almost impossible for some of them to win given some matchups…but I love it anyway! The bluffing involved as you play cards face down, making players try to figure out if you are playing something they have seen before or the new card you got that round is always entertaining to me. The agony of waiting for that powerful card for your clan to come up, only to have it be the one card in your deck you do not see the whole game. The clever combos that you can make are fantastic. The main downside is since it is just three rounds, you don’t get a lot of time to play with them. Also that in order to win, you cannot put all your cards at one location. You really need to place in two locations to make enough points to win.
Betrayal at House on the Hill - Played the first edition of this at a friend’s house once and I was immediately hooked. The large number of possible haunts, the wide array of event and item cards, the crazy way the house builds up, all combine to form this (potentially) incredible experience. Yes, you get duds sometimes, and somehow the blob scenario pops up all time time to the point we started skipping it, but when it hits, it is magic! I just wish they had kept the Underground Lake as an Upper Floor tile!
Love Letter: Batman - I have not played every version of Love Letter, but from what I have read, this is considered one of the best. Gaining a point by correctly guessing an opponent’s card with Batman always feels good, and the little tidbit how you don’t get a point if you guess Robin, since he is a good guy, is just funny. Super portable, quick to play, even if just killing some time waiting for something else. Heck, four of us played this while standing in line for a SHUX event! I can’t not include it!
Honorable Mentions:
Coup - has to be one of the best bluffing games, and it’s always hilarious how everyone starts out claiming they have a Duke for the extra money. 
Tokaido - just a very chill game, perfect for unwinding after a hectic day. Love the art, as well.
Royal Visit - really enjoy the tug of war between both the king and his retinue, and the crown token. Brilliant little game, and the new edition is gorgeous.
Zoo Vadis - with more plays, this might go into the top 5, but can’t base that on just one play.
V-Sabotage - really enjoyed the PbFs I played on here, to the point I backed the last KS for it. Only played it once since then, and really need to remedy that.
A War of Whispers - similar to ZV, only had one play, but it was fantastic.
Maquis - great solo game, even if you can lose on the first turn with some bad luck.
The Bloody Inn - I really enjoy this game. It can be a bit of a brain burner figuring out what to do, whether build an annex for the special ability or to murder a guest, as you need the money to win, but still making sure you dodge the police. Plus, which cards do you use to pay for your action? You really want to build the annex for the one card, but can’t afford it yet, but you could also really use the card to hire some more accomplices. Lots of fun decisions.
Mystery of the Abbey - I don’t quite know why I enjoy this improved version of Clue as much as I do, but I would never turn down a game of it. I think it is the clever questions you have to come up with in order to get the most info without giving it to the whole table. It almost always ends in a final turn where everyone is racing to get to the room to make the accusation, but if you’ve been playing well, you have made some good guesses about the traits of the murderer throughout the game and can win even if you aren’t the one who names them. Always enjoy this.
Escape the Curse of the Temple - Frantic dice rolling at its finest. Short, simple, fun.
And how can I not sneak Unmatched in here? Only two boxes are in the top 500, meaning the average of them all is probably outside of it, so I am adding it as a technicality. Goes in the top 5, easy.