Madden '98 and Madden '03 were my favourites. I never cared much for Madden before '98 as I felt the player momentum felt like guys on skates. But the first year they went polygon and added the juke move, I was in heaven. I loved '98 and I played that game with the Blimp cam. One year (not sure when but soon after), my brother and I just did a sim 30 year franchise. I won two Superbowls with Miami while my brother got fired two or three times before finally sticking with Tampa Bay. However, he won three Superbowls. He also constantly abused the trade logic trading backup centers to the cpu for first round picks.
Madden '03 was my favourite PS2 game and I played the heck out of it. I still remember having a lefty, scrambling QB for the Dolphins and he was a blast. At least until the next exciting QB prospect came along.