Hard to narrow down on my end, but here's an attempt at five, with a few stories I've told a few times here but here goes again:
1. My First-Ever Wrestling Show
Estimating around July/August 1987. I was a few months away from my ninth birthday, living in a small Northern Michigan town called Oscoda. On Saturdays I was glued to the TV watching WWF Wrestling Challenge, NWA Worldwide, World Championship Wrestling on TBS, and so on. But our town was a couple of hours drive minimum from the closest place the big leagues were touring.
When my father wanted to talk to me about serious stuff, or just needed to get out of the house to sort some things out, he would go for a drive and take me with him. The slang term he used to describe these drives was "going crazy". One Sunday evening he pulled me out of my bedroom to go for one of these drives, and he picked up a couple of his drinking buddies that lived down the street.
He drove to a town that was about an hour away from ours. The drive seemed like nothing out of the ordinary, until he pulls into the parking lot of Ogemaw Heights High School in West Branch, MI, a school off of Michigan Highway #33 surrounded by nothing but trees and fields. The letters on the sign of the high school simply said "WRESTLING". I got super-excited, and at first my father and his friends joked around saying "nah, that's tomorrow night, we're going to bingo tonight!" But sure enough, once we're inside the school we head into the gym and there's a wrestling ring in there. My dad frigging surprised me on a random summer night by taking me to a wrestling show.
I don't remember a lot of specifics. I think the league was called Michigan Championship Wrestling. It had some of the guys that I found out years later were part of the final days of the Sheik's Detroit territory, guys like Irish Micky Doyle and Ricky Cortez. And a young Al Snow was part of a heel tag team calling itself the Fantastics (which confused me a little since I had seen the Fulton/Rogers version on UWF and World Class TV by that point) against a tag team called The Flying Tigers. The Fantastics cheated to win their match, but sure enough there was a battle royal at the end of the night, with the final four being the Al Snow version of the Fantastics and The Flying Tigers, and the Tigers got their revenge by winning the battle royale.
But the biggest actual name of the show was future WWE Hall of Famer Bobo Brazil, once again defending the "The United States Championship." Bobo was into his sixties by then, but I had read his name in grocery store magazines enough to know that I was seeing a legend in the ring that night.
But the biggest smile of the night came when Bobo Brazil came down to the ring. My dad never watched WWF wrestling with me, and would always joke about how phony Hulk Hogan was. He never did it in a mean way because he knew it was something I loved watching, would always be more in a joking manner. But that night, when Bobo came to the ring, my Dad pulled me aside and said the following words..."I used to watch him wrestle when it was real!"
2. ECW's first-ever Detroit-area show
One of the rare ECW shows where no RF fancam exists. A year before they started doing TV tapings at the Michigan State Fairgrounds Arena, ECW did a show at the Inkster Recreation Center. This was actually my first live wrestling show since the above small-town show ten years earlier. Me and a friend did not have advance tickets, and only really knew about the show from a one-item line listing on 1Wrestling.com. We were still living in our small town at the time, about a four-hour drive north of Detroit. We decided to make a day trip out of it, and left our town around 10AM and got to Inkster around 2PM. We figured if the show was sold out, we had a day trip in Detroit. We roll up to the rec center lobby and see a woman working a check-in booth. We ask if tickets are available and she said "we don't have any tickets!" We asked if the show as sold out, and she clarified that they don't have tickets because no one from ECW had given them tickets to distribute yet. My friend sees a man walking around wearing an NJPW King of Sports jacket, and assumes he must be with ECW. We ask the jacket-wearing man if he knows when tickets are going to arrive, and he says "I got them, come with me". He leads us to his car in the parking lot, and opens up his trunk. He takes out a batch of tickets, and says they are $20 each. I start rifling through my wallet but am fumbling around through a bunch of 5's and 1's, but he thinks I am fumbling because I may not have the money. And it was at that moment that Pee Wee Moore asked if we had any weed and offered up tickets in exchange for that. We did not have any weed on us though, but the cash ended up in Pee Wee Moore's hands, and I would not be shocked if that money never made its way to HHG Corp's books.
Main event was Sabu vs Sandman which was as nuts as expected, including Sandman jumping off the apron to put Sabu through a table only to bounce off of him into the front row when the table didn't break. We also got a good and bloody New Jack/Kronus vs Dudley Boyz match, and to this day I still have my ticket that I had dipped in New Jack's blood on the floor.
3. "R.A.W. COMES TO TOWN!" (R.A.W. = "Renegades Alliance of Wrestling") and Terry Funk makes an indie date on the same night as a WCW PPV booking two hours later and 700 miles away.
I went to college in the Upper Peninsula of Michigan, a small city called Marquette, home to Northern Michigan University. The local celebrity was Mike Shaw (Bastion Booger/Norman The Lunatic), who was a native to the region and retired there to raise his family once his WWF days were over. He would work at a local copper mine during the summer, and while school was in session, he would work nights/weekends as a doorman/bouncer at one of the more popular college bars in town.
About once a year, a money mark would try to promote a wrestling show in the area using Shaw as a draw, but would never be more than a one-off. I recall there was one with a local casino that brought in Brooklyn Brawler to work Shaw, and there was another one at one of the area hockey arenas that had a fake Doink and a fake La Parka but somehow had real Meng while he was still under WCW contract. But the most notorious of these one-offs was when "R.A.W." came to town. And when I say "R.A.W.", I mean the Renegades Alliance of Wrestling.
The main event was Typhoon vs Tatanka, the semi-main was a tag team match of Sabu/Bruce Hart vs. Brutus Beefcake/Greg Valentine. The promoters rented a frigging BOXING ring from a local gym, which would have been bad enough if it just meant guys bumping on a hard boxing canvas, but they used the boxing ROPES as well, so damn near anything involving running the ropes or climbing the ropes looked like shit, though god bless him that didn't stop Sabu from making three attempts at a springboard bodypress to the outside onto Beefcake, who didn't make any effort to protect Sabu when the rope sagged forward and he went splat on the floor.
But this was also the night that Terry Funk endeared himself in my heart forever. The week after flyers/radio commercials for the show started floating around the area and he was advertised as one of the wrestlers appearing, Terry Funk started showing up on WCW TV again. An angle ran that lead to Terry Funk being booked against Kevin Nash at WCW Souled Out 2000...on the same night as the "R.A.W." show.
So naturally, my friends and I assumed that Funk would not be appearing on our show. Before doors open, we ran into a friend that worked for the local TV station and was there in the afternoon recording pre-show interviews for the 6PM news broadcast that would air a couple of hours before bell time for last-minute promo. He told us Funk was there (side note: the same promoter ran another town three hours away the night before, and one of the undercard wrestlers has since told me that Funk worked the night before in a falls-count-anywhere hardcore match against Shaw and got Muta-level juice when a trash can spot went wrong, which of course is now a holy grail match for me if anyone recorded it that night), and the plan was that Funk would go out to open the show and then immediately hop on a plane to the WCW PPV, which was in Ohio that night so a quick flight was doable provided weather panned out.
The show opened with one of Shaw's trainees - "The Irish Luchador" Billy McNeill who ended up working St. Louis indies for a while and running in the same circles as folks like Matt Sydal and Delirious prior to their ROH days - receiving the "R.A.W. Rookie of the Year" award, and then Terry Funk comes storming out of the locker room and assaulting McNeill and issuing an open challenge to anyone in the locker room, which summons Bruce Hart. Bruce Hart and Terry Funk then do a wild five-minute brawl all over the gymnasium before they end up tumbling through a door to outside the gym, where I assume a car was waiting for Funk. Bruce Hart of course being Bruce Hart, comes back to the ring, and on a show that was in a high school and had been promoted as "family-friendly" immediately starts calling Funk a "chicken shit" on the mic.
It may not have been a proper match, but Terry Funk cemented my fandom forever that night by still showing up on the same night as a WCW PPV booking, when everyone would have understood if he canceled off the show.
And yes, the promoters really did say "R.A.W. Comes to Marquette!" on the flyers/posters promoting the show. In January 2000. When WWE RAW was red-hot.
4. IWA-Mid South Something to Prove - front row for Samoa Joe vs. Necro Butcher. I can be seen freaking out multiple times on video. To this day, that match is still the closest I have ever felt to experiencing "BIG FIGHT" euphoria and delirium. One of the most epic wrestling weekends ever. Caught overnight flight on Friday night out of Los Angeles, landed in Philly Saturday morning. Went to the IWA/CZW double-header at ECW Arena with friends, then we drove together to NYC Sunday morning for Puerto Rican Day, the ROH show, and the first ECW One Night Stand. Then caught a 7AM flight Monday morning back to Los Angeles and was at my work desk by 10AM Pacific time. I had no vacation days with work at the moment, hence me not being able to take Friday and Monday off and missing Hardcore Homecoming and having to make the whirlwind weekend. I was drunk the entire time from Saturday morning flight landing to Monday morning flight returning with maybe eight hours of sleep total for the entire weekend. WORTH IT.
5. Joey Janela's Spring Break 2019 - I was at G1 Supercard in MSG, and getting really nervous about the timing for taking the train from NYC to Jersey City and getting there in time for JJSB. Okada vs Jay White took the ring at MSG, and as much as I wanted to see an IWGP Championship change, I couldn't help but pull the trigger on bolting early for Spring Break. I speed-walk from the Jersey City train station to the GCW Collective venue, and as I walk in the doors, Rich Paladino is in the ring starting the countdown to going live on FITE TV. I literally could not have timed my departure from MSG better.
And my departure from MSG meant I got to Spring Break in time for what was the main draw for me that evening. My first non-WWF wrestling as a kid was Jim Crockett Promotions 1986. Throughout many years of attending WWF/WCW/ECW events in the late '90s, and Wrestlemania weekends and numerous independent shows in the 2000's, I still had yet to see the Rock N Roll Express wrestle live. I finally got to cross seeing them off my wrestling bucket list with Spring Break that night, and on top of that, it ended up being a damn fun "passing the torch" match with LAX/Ortiz & Santana/Proud & Powerful. Seeing Ricky Morton live hitting every move crisply brought me great joy that evening, and I 100% lost my shit when Morton hit a perfectly-executed Canadian Destroyer. And the post-match where RnR presented their bandanas to LAX...I still have yet to actually cry while watching live wrestling, but that may be the closest I have come.
I missed the IWGP Championship changing hands, but I honestly would have been much more bummed out if I had missed the Rock N Roll Express tearing it up that night.