I can't speak about a smart phone directly since I don't have one. My flip phone is my only mobile phone since I prefer its simplicity and that the screen is protected from damage (I've seen so many smart phones with a damaged screen that I'm no longer surprised by it). I also like the long battery life (I can go several days on a charge with regular use). One difference between the two is the interface. One of the things I like about my Walkman is the interface. Some knock it because it looks like something that is a bit ancient (except for a few improvements it is the same interface used in the original MP3 Walkman over a decade ago). But I like it because its simple and it works. Plus, I like that it does not have a scroll wheel like on the iPod. While the scroll wheel might be okay for a small number of files, when you start getting into the thousands it takes a long time to get to a specific song, even with the alphabetic shortcut. For me, the diamond button (a square turned 90 degrees with a button on each corner and a button in the center) on my player is much easier to maneuver around so I can get to any song on my player (a little more than 7,000) in a few seconds. One thing I dislike is a touch screen when it comes to music players is because it usually takes a lot of finger swiping to get to what I need. I had a Walkman with a touch screen and it turned me off of touch screens for music players, and that is a real I'd give a pass for a smart phone as a music player...unless I can customize the interface to suit me.