Here are the 4 most 'Boss' times I can put together from memory showing style as you suggested in the OP:
NOTE: In my beginning years of gambling, I would definitely be inclined only to remember the highest winning shoes as memorable shoes/trips. As time passes, it is more about uniqueness and 'stand-out-ability' with the most memorable. With that said, here are mine anyways:
3 from the 90's and 1 from 2011.
The last one first. 2011 @ The Bellagio, very late afternoon waiting on the VIP Super bowl Party they have in their ballroom for invited guests. Played one shoe of Midi Bac and won about $50k. Then we went to the unintelligent behind boring SB party in the ballroom to watch 2 teams I couldn't give 2-hoots about, Steelers and Packers. The following two shoes at that same Bac table were killer shoes for the players and I remember to this day Johnny F. and the dealer as well, both telling me how 2 players each took them for $200k and $300k respectively. I have said for a long time that good shoes comes in groups of 3, but I got caught up in the events, and lord I hate doing that, I am a gambler and really don't go for the shows and events, sure I go to some of them but not as the primary reason for going to Vegas, I still regret not staying at that table. I have played numerous times where I arrived after all the great shoes were done or I left early, etc. But never played 1 of three great easy shoes where it was possible to rake in hundreds of thousands.
The next 3 are the happy ones.
The 80's and 90's to me were more fun in Atlantic City because of the type of players. Vegas had more California and west coast players as the majority and they tend to be much quieter and love to subscribe to that 'heads in the hands' syndrome at the tables. On the other hand, before 9/11 and of course before 2008 economy crash, Atlantic City had the boisterous, loud, continuous high-fiving/backslapping players that egged on the camaraderie beyond belief. Generally, the quieter times and less boisterous ones in Atlantic City was about what Vegas was generally like the majority of the times.
First time playing at Bally's Grand after the Steve Wynn days of his first casino owned by himself, The Golden Nugget. I was playing the carnival game '3-Handed Blackjack' on the main floor where you would keep your first card for the following two hands. I was up about $25k to $30k or so and my x-wife's friend grabs me by the arm and yanks me away. She brings me to the big baccarat table in the HL pit there. This is the time when there was no Midi or Macau style, only 14 seat/3 dealer big tables or mini bac on the main floor. I sit down next to her and her two sisters and there other friends all taking up one side of the table. I begin winning and whatever I touched won. The whole table, full with 14 players, begins to follow. 1/2 Asians and 1/2 White people. Most know each other and most of the dealers are all on first name basis with almost everyone. Well over $100k up after a shoe or two. We ripped up cards, threw cards out onto the main casino floor, all kinds of 'normal' bac stuff that unless you played during those times, you really have no idea. The dealers back then rarely made mistakes if ever. All shoes were hand shuffled between games taking at least 20-25 mins between shoes. Then we all ran to the main floor mini table and the floor people knew us and we were allowed to wager $100/$10k or whatever our max limit was in the HL at the big table. The regular players at mini were only allowed $25/$2,500. We would all group up and let 2 or 3 players squeeze in and hand that player from the big table our wagers for the hand. It was so loud and complex with the wagers, at least 2 if not 3 floor people would come running over when we all hit the couple of mini tables during the big table shuffles. It was fun. Once in awhile one of us would reach over and grab a card from the dealer before they turned it and we would squeeze it. They floor would shake their heads as then the cards would have to be changed after the shoe of course. But no one got upset, we were the players, the customers, unlike today's atmosphere. When the whole side was on one side and it lost and the results looked 'not so obvious' some of the dealers would do the wrong pay-out so quick if the floor people were not watching, you could never catch it. Like if the Players had a 6 for a 3rd card and the Banker was sitting with 6 for the first two cards, say the Banker drew a seven or a 9, the dealer would glimpse at the floor and if they were not making eye contact, a lighting fast payout to the Banker would happen. It was just the way it was occasionally and no one ever got caught. This is before the pits had the regular lounges and food, the Butlers from the private floor were called if we requested and they would go to the boardwalk and bring back 6 or 10 boxes of pizza pies and calzones from a small place on the boardwalk just north of the Grand there. But the camaraderie and the people made the scene by far and there was never a lack of it. I played here numerous times when it was Steve Wynn's joint, The Golden Nugget and after it went to Bally's I left there for the Trop/Tropicana, The Claridge, The Taj, and Caesar's to play bac. After that night I was a regular playing back at The Grand most weekends.
The next one was at The Tropicana in Atlantic City also. This is when the HL was all the way in the back of the place, I believe it would have been the west end of the casino. It was like an alcove set-up. The one big bac table they had was in the rear corner of the room. It was a full table one night. As quite frequently one side (7) players would wind up wagering the opposite side wager's than the other end of the table. A massive run came and the guy next to me had the shoe to my left (I would get the shoe next to deal). After about 3 or 4 hands he is way over confident as most of us were back then when the shoe traveled around the table. He was standing up and motioning for everyone to wager Banker. Like a Crazy Eddie (New Jersey/NYC electronic store chain-very infamous famous) commercial, exactly, the guy was actually yelling and screaming for everyone to get on the Banker. His arms waving widely, egging each and everyone to wager Banker, really getting into it. Real old school bac action and fun. (for those of you who have no idea who Crazy Eddie was, Google him and read)
The guy makes a couple or a few more Bankers, we are all wagering Pumpkins/Orange and up I think. Most of us are wagering up $5k to $10k a hand. I think there was only two hold out other players wagering on Players at this time. One was to the guy's left in seat 1 and the Banker was in seat 2 and I was in seat 3. The guy in seat 1 returns a Natural 8. The guy quickly looks at his two cards and they are both pip 4 liners. I stuck my head over and he did not see if they were 10's or not and there was another couple of players that jumped up and ran over to his back as well. The guy that retuned the players natural is all smiles and shrugging his shoulders, I can still see it clearly to this very day. The guy with the bank breaks out singing the old "Stealers Wheel" song, 'Stuck in the Middle With You'. Clearly and loudly breaks out in perfect harmony, "Clowns to the left of me and jokers to the right....I don't know why I came here tonight....I got the feeling something ain't right.....Clowns to the left of me and jokers to the right...Stuck in the middle with you". The guy slams down a pip 10 card. After a good 20 seconds or more, the guy breaks back out "You're proud that you're a self made man, and your friends they all come crawlin, slap you on the back and they say"...... he looks over at the guy with the Natural 8 and in a long drawn out verse, says "nine" and slams down the 9.
The guy with the shoe continues, makes a few more bankers, probably up to around 9 or 10 by now. Gets up even a few more, probably around 15 or so. Everyone is on the Banker now of course. (LOL, these days most would be playing for the inevitable cut missing it all, LOL!) The guy's with his wife who is now standing behind him, we are all up easily well over $100k, house down well over 1 million, suits everywhere, hosts, HL manager, casino manager, others, security hanging around, etc., the guy and his wife both break out singing "That's the Way I Like It" by KC and the Sunshine Band. Perfect lyrics perfect tone! They both keep it up until he is done with his banker run, I think it was just under 20 or maybe 20 with the ties.
Runner up 4th, almost put it as third but the others beat it out. I think of this one all the time. At Caesar's in Atlantic City also. Mid 90's. Asian/Chinese New Year. Popped in Caesar's from another property there in AC. The HL was pretty packed. Seemed all the people were pretty much their own crowd. In the original high limit room, not the later side step up area with the Asian games. This was the big tables, smack in the middle of the room. Most all looked Filipino ethnicity out of the Asian that were seated. They just started a shoe and I grab the one seat that was open. I learned that they were pretty much winning and following their one 'leader' of sorts. Everyone was on the same side and I mean everyone, every time. They would wager and then sing a song, I had no idea what they heck it was. Almost every hand every one was winning. The 'leader' would wager first, every one followed. They would even switch sides after wagering before the cards came out and of course, they were right. The shoe took a phenomenal 4 to 5 hours I remember, The house lost millions that day. Another great game that I remember.
Those are the shoes and trips I will never forget, my top four. There were plenty of other great ones, but those are in my fore-front when I think about the past.