the I in #1 doesnt stick out enough as well. Both #1 and #2 are good overall and it's a tough pick. I think #2 would be better for a younger crowd, particularly white / american culture and not the hip-hop culture. Would go over well with more famos high class.
#2 would go over better with older people and the hip-hop / hardcore crowd. For younger people #2 will attract the less smart ones I believe.
EDIT: The straight angle of the writing is what also makes #1 look like it's older. It's one of the main differences between them, the slant of the writing.