First is Gross Point Blank. Nothing more attractive than a man that can kick ass whilst being a tortured soul....what could possibly be more appealing? (Hugh Jackman as Wolverine.. possibly). Anyway, very funny, dark, and, of course, the 80s references that I, oh ma gah, love.
High Fidelity is one of my favorite movies (the book is great too). I think, Jack Black's best performance. And the movie touches on some of my own themes, music and critical snobbery without actually having talent yourself. Again, very funny and relative. You can watch them over and over...I do.