Most S60 devices have built-in music playback capabilities and double as a portable music player for MP3 and AAC tracks. The music player speaks ID3 and allows you to navigate your music library by artist, album, genre etc.:

There are a couple of ways to transfer music from your Mac to the S60 device. The simplest one (but also the most primitive) is to simply drag the songs either within from Finder or iTunes on your Mac to the memory card of your phone. As the files can be rather large, I find a non-Bluetooth mechanism fastest. Once again, there are a couple of options: either use an external card reader to directly write to the memory card of your phone or use the phone as a USB mass storage device directly. The USB mass storage mechanism is a little slower but works fast enough for my purposes, and avoids the hassle of pulling the memory card out and playing with an external reader.
Once the music files themselves have been moved, you need to launch Music Player on your phone and select Options > Refresh Music library... to update the song index. This will take a few moments, depending on the number tracks on your phone.
Nokia also provides a piece of software called Nokia Music Manager for Mac which I am yet to take for a spin. The page indicates that the application is for the N91 multimedia computer, so I need to test whether it works as specified with other S60 devices.
Another option is to have a look at the rather excellent SyncTunes software at http://www.nesfield.co.uk/synctunes/ (free/donationware). SyncTunes provides a straightforward mechanism for synchronising a given iTunes playlist with any external disk volume, and using either a card reader or the USB mass storage functionality achieves exactly this.
SyncTunes has a great deal of customisable options, but has reasonable defaults at least for my purposes. When you fire up SyncTunes for the first time, you need to select the iTunes playlist and the external volume (your memory card) to synchronise with. Here is an example of my settings:

Once the playlist and the target volume and folder (I use Music) have been selected, all it takes to sync the tunes is to click Sync. SyncTunes also remembers the settings from one session to another, and allows you to define profiles for multiple different sync operations (e.g. for different phones).
Once SyncTunes has been set up, all it really takes to have your iTunes and your phone tunes synchronised is to take the following steps:
The above operation is smooth enough that I've actually started shying away from dragging my trusty old iPod mini along anymore, as the phone is with me 100% of the time anyhow, and usually with a headset. The mini is finding still some use in occasions where the larger capacity is needed (e.g. longer travel), but I actually find myself listening more music and more often now that I do not have to worry about keeping 2 separate devices synchronised and charged at all times. But as always, your mileage will vary.
Also note that music bought from the iTunes Store will not play on anything else than an iPod until Apple makes non-DRM tracks available (any day now, basically, for the EMI catalogue at least).
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