Let me first state that I love this thread. It helps bring back memories.
Ok, I never was an Usher fan for some reason, and I'm sure most people will praise "Confessions" but I won't....thought it was overrated. JMO.
If I had to choose, it would be My Way, because it's when he started becoming popular (fun videos, playing on "Moesha", etc.) and features the only Usher song I ever liked or cared about-- You Make We Wanna.