For the "cool" factor the iPhone ranks pretty high up there. I think the Blackberry is probably a better phone functionality wise. I'd also consider the Android phone(s) that are out now. Google has really made a great mobile OS and have some really cool apps plus it's fully open for development, contrary to Apple's approved application development where they choose only the apps they think are ok for the phone, which is a huge negative.
I've had some issues with 3G connectivity, dropped calls and calls that never ring and I just get a voicemail. That could be AT&T and the area I'm in getting slammed on the data side (I live in LA so it's very saturated here). I've heard this problem from several users as well so I know it's not just me. I went with it becaues my Razor was falling apart and needed a new one. It's pretty cool and works as expected, I just think if you are looking for something with more functionality then it's not for you.