I'm a huge fan of the classic iPod; I use mine most days, and have an extensive music collection that I like to take with me when travelling (and I travel a lot).
Actually, the classic was my first Apple product, I'm a typical example of the so-called 'halo' effect leading to the purchase of Apple computers as a result of having bought, and loved, the iPod.
Even more than the form factor, (which I love), the sheer ease of use when ripping and burning (especially when compared with the tedium of burning and ripping CDs on the old Windows software - I lost count of the number of blank CDs that I destroyed accidentally), the fantastic sound quality, the wonderful portability, apart from all of that, Apple's excellent customer service was what won me over.
Sad to relate, the classic has one slight drawback sometimes, which is that some of them (equipped as they are with the old style HDD, rather than a SSD drive, as are the Touch and the nano) die a tragic death. The HDD simply lies down and dies. This happened to an iPod classic of mine, and, as it was still under warranty, it was replaced without any fuss. It happened again some years later (another HDD failure with another classic), which, as it was still under warranty, led to the same happy outcome. Thus, I became what is known in the parlance as a 'switcher' and have never regretted it.
Moreover, as long as the classic is made, I expect that I shall have one or two of them in my briefcase, or by my bedside (and, indeed, sometimes in my office, too) to keep me company. Nothing beats a classic as company on long plane journeys, or on trains, or a bus, or any form of transport where many hours separate you from your planned destination.