****, I'm really lucky to say there are a lot of them to actually rank. We had season tickets in the OB for a long time, and were fortunate to attend a lot of games together.
But I would probably say as soon as Bandy broke on that pick six and the couple minutes that ensued. A game is never totally over in the first half, but that one was about at sealed as it could possibly be, and it really felt like we might be "back". So, I'm 43 and have a lot of memories from my younger years of incredible Cane moments, but most of those were in the glory years and it almost felt expected, if that makes sense? The ND game/Bandy moment was a lot of years of frustration coming out.
I remember sitting directly next to him, and YELLING literally as loud as I possibly could, right into his ear. He looked at me and shrugged. Couldn't hear a word. If we were in a quiet room, I'd have probably put him into the hospital with how loud I was screaming into his ear, but in that moment, he couldn't make out a single syllable. That's how ******* loud it was. Simply incredible, and one I'll never forget.
A couple honorable mentions of watching with him in person:
2000 watching Shockey beat FSU
2002 Wide Left
2003 Kevin Beard to go up 38-33 against the Gator
1998 Miami 49 UCLA 45 (still to this day one of the top 3 most fun games I've ever watched in person)