Surrounded
In 2000, based on mentions of DT in the Megadeth forum, I downloaded this song to put on a mix CD. I was into my metal phase, and this was the song I downloaded for some reason (Napster maybe). Suffice to say, I hated it. I was at the time not into 80's rock/metal, and that is what this sounded like. So at that point, I wrote them off.
Pull Me Under
In 2001, my cousin played the song for me. I enjoyed it, and I bought I&W shortly after. However, with Surrounded being on the CD, I still had the 80's vibe (thanks Prater!). So I tried and tried, but pretty much gave up hope.
Hell's Kitchen
A few months after I bought I&W, I decided to give DT a shot again, why I do not know. I think on CDNOW maybe (I think that was the site, prior Amazon explosion), I listened to a sound sample. I loved what I heard! So after a trip to amusement park with friend's was cut short, I decided I was going to go buy the CD that had the song when got home.
New Millennium
...and this was the song I needed to hear. With my current musicial maturity at the time, this is the song that ultimately did it. I was into Nevermore at the time, so I was getting used to high male vocals. But I&W was just too high at the time. This song had enough vocal restraint that just clicked. The instrumentation was controlled by bombastic, and it was heavy enough for me to keep my ear.
And the rest was history. I bought the whole back catalog at the time, and eventually loved I&W. But at the time and place I was at, it was hard to appreciate. And the production really does date the album, it is true unfortunately.