This is a question that I've often wondered. Chances are that this is a question that likely has been posed on BCB before, and if so, I apologize, but since I'm quite new to the site... (also apologize if my posts are not formatted well) Obviously this will alienate those not old enough to have survived the disappointment of 1984 but...
1984 was such a magical season. I STILL get bummed thinking that I missed the 'Sandberg Game.' on the NBC Game of the Week. Went guitar shopping with my brother that afternoon. Like it is for most Cubbie fans, Cubs/Cardinals is my favorite series. Never miss it. Either on TV or at Wrigley. And being from Michigan and a lifelong Tiger fan too... the 84 season was magical one for BOTH of my teams. And the shot at a Cubs/Tigers World Series... Always been my dream to see that. So close.
2003... Obviously the excitement up til the 'Bartman Game...' Watched every game from my perch at BW-3 in front of the BIG screen. The excitement of being with the gang... the disappointment... Once again... so close. It was so surreal. Still IS.
The strange thing? You hardly ever hear Cubbies fans mention 2007 or 2008 as far as the disappointment. Both those seasons were hard to take too. For me, 2007 was real hard because for the first time it was from the front line. Spent much of 2007 IN Chicago and at many games at Wrigley. And of course 2008 was hard too. To have such a great season... the 100 year anniversary since winning a World Series... But both 07' and 08'... the Cubbies were knocked out of the playoffs so quickly, so decisively... didn't have the same feeling of angst as 1984 or 2003. For me... 2003 was the hardest. Followed closely by 1984. Then 2007. Then 2008. It's hard to rank them. How much are Cubbies fans supposed to take?? But being that close... it sucks but... beats the Hell out of a season like this.