I voted 2004 without hesitation. It has as much to do with what happened as what was going on in my life at the time.
I was living in New York City and was in Greenwich Village when Aaron Boone ended the 2003 season for the Sox. It was crushing. I remember that shortly before then, a deep anger and resentment at Yankees fans bubbled up inside of me. They were finally going to feel what we felt our whole lives. Turns it it would have to wait.
I was 27 in 2004, and had more time on my hands than I do now. In various states of unemployment, I didn't have much money but life was much simpler. I did have enough to have the MLB.tv package on my computer. I probably missed some games that year, but it felt like I watched every single one. I had figured out all the Red Sox friendly bars in the city, and for every ESPN or nationally televised games I was there. One particular game, a late season tilt against Baltimore, I was in a lower west side bar. It was post-trade so Alphabet and O-cab were featuring prominently, the former on D. There was some crazy double play with an out at home (maybe with Leskanic pitching?), and O-cab had a big hit. The magic was starting to happen. I had been pretty loud (as I usually am). I was going a little nuts. Somebody came to the back room to look at the TV, and then looked at me, nodded and smiled. It was Philip Seymour-Hoffman. I smiled back and nodded.
That whole August was a great time to be a Sox fan. It was fun, crazy, improbable. They had been underachieving and then they started to achieve the shit out it. I got to see it all. A time like that may never come again.
I was in the bleachers when Big Papi took Jarrod Washburn deep to win the ALDS. I was in Brooklyn when they took the 19-8 whooping and I tried to deal with it by drinking until the sun came up, but it didn't work. I set up a shrine with pictures of the team and candles and weird offerings intended for some sort of jobu-like baseball god. I walked to the subway that morning(or was it two days later? My liver wasn't sure) with my Sox hat on to catch the Fung Wah to Boston to go to game 4, seeing many shit-eating grins of Yankee fans who met my glance with an air of superiority. I sat in the same seats in the bleachers when Dave Roberts stole second, and watched Papi's homerun sail toward me into the bullpen. I watched game 5 in Boston with friends, actually watching the TV in a huge mirror to reverse our fortunes. I came back to New York City for games 6 and 7 and watched it all unfold. I rode the subway the next day with my hat on, and locked eyes with a man in a Yankee cap. He looked down. In my entire life, that had never happened before. Everything was about to change.
At 3-0 in the World Series, Rob Corddry filmed a Daily Show segment in my house. He was interviewing my then girlfriend as someone who was injured by voting. They came in and looked around. He saw my shrine, and pointed at and looked at me with his eyebrows raised, like "Riiight?" He said, "I can't believe I'm saying this, but I think we got this. I feel good." I nodded and no more words were spoken about that subject. There was a tacit agreement: We agreed on what was said, but we had already said too much.
That season was so rewarding as a fan, especially because of the season that came before it. Living in New York City while it was happening was particularly awesome, and could've been the other way. I got to celebrate in their house ALL YEAR LONG. I remember at random times from October to April, I would just laugh to myself and say "The Boston Red Sox won the world series!" I would call people and that's all I would say. I did it just because I could.
What followed wasn't better or worse, just different. 2005 seemed like so much pressure. I wanted another one, and they did too. It didn't happen that way. 2007 and 2013 were amazing, amazing years with different characters and storylines. Both teams did it right, but nothing NOTHING will ever beat the Greatest Comeback In Sports History™, the vanquishing of an 86 year old curse, "Why not us?", a band of merry idiots, and a time in my life where I only had to answer for myself, where baseball could be the most important thing in my life. After that, I had to start growing up.