I speak for my own experience here, so feel free to compare your experience with mine. You may find something in my experience that you missed that you can try out. If you see something missing, let me know. I'd like to hear about it.
I remember the days of radio. Some people still listen to the radio in the car. I used to listen to commercial radio every day. I stopped listening to my own music in the car because I couldn't seem to get a good recording of my vinyl LPs to tape. So I listened to the radio.
My experience with commercial radio is to listen to music I don't like for about 30-40 minutes with a few commercials and DJ blather in between, only to find one or two songs in a set that I liked. The songs that I liked were often pretty old songs.
I also noticed that the commercials were doing something to my thinking that I didn't like. At some point in my life, I just decided I didn't want someone telling me what to do on the radio. So I switched to public radio. I found KCRW and KXLU (both of which are now streaming through the Internet). Morning Becomes Eclectic and Metropolis on KCRW turned me on to entirely new genres for me. KXLU seemed to play everything that was underground, that was fine with me as I was already bored to death with "hit radio".
So I got some relief from commercials there. But I still wanted to listen to my own music. When I got my first CD deck with a CD changer in my car, I was playing my CDs all the time. Every week, I'd change them out and listen to what I wanted. I rarely listened to the radio then.
Then I discovered that I could install a stereo that would play music from a USB drive. Now that was cool. I thought about an iPod, but I really don't like Apple. The market had been saturated with Apple only solutions, so when I found the USB drive solution, I was very happy.
Every week, I would fill up the drive with 1GB of music and drive away happily, playing my music. The stereo display would show me what was playing and I'd know if the song wasn't familiar to me. It remembered what I was playing when I turned the car off during the previous use and picked up where we left off. I could turn off the car, take the stick with me and then plug it back in. The closer, the feature I liked the most, is that losing a USB drive was not a big deal, so I could leave it in the car. Losing an iPod, that's a big deal.
I wasn't so lucky on my next car. The auto manufacturers have not been kind to aftermarket manufacturers, seeking to subvert the will of the car buyer from buying a stock radio and going to an aftermarket shop to install a CD deck of their choice. I could have had a CD changer, but they wanted $1100 for that. That is a lot of money for a changer.
I did find that there was a charger port and a sound port for music devices in my new car. So I tried different devices, but nothing really suited my needs. That changed when I got an Android phone. I found that I could pack music on the internal SD card and play from there. The stock music player left much to be desired.
While I was waiting for the stock music player to catch up, I found WinAmp for Android and played streaming music from stations I know and love: Groove Salad, Zone Drone, Cryosleep and Blue Mars. WinAmp had problems making the transition from Wi-fi at home to the cellular network, so I looked around and found Tune-in. That is a very solid music player for Internet radio.
Although I still like Tune-in, I noticed something new for me at the time. Pandora. I tried Pandora at work, then found the Pandora app for Android. But I still wasn't playing my own music, thinking that the stock music app was lagging behind everyone else.
When I found Google Play, I thought I might not want to upload all of my music to the cloud. After much consideration, I gave it a try. Google is very good about supporting Linux, so there was a Linux client I could install to scan my library, upload the music and then play it back through my browser if I wanted to. A few interesting points here: it's free and, it's based on the number of tracks, not the amount of space used in the cloud. That's nice because a few of my songs are more than an hour long. And I like to use FLAC for ripping CDs.
Now I can listen to my music anytime, anywhere. I can use my phone or any browser on any computer. I use Chrome because it just works better than any other browser out there. I use Google Play on my phone when I'm in the car. This method does use the data plan and with daily use, the maximum of 2GB can be reached. But it seems to be the best solution.
Notice the trend in my experience. All solutions eventually lead to streaming music, even for my own music. Streaming music is a wild fantasy for music lovers. The downside is being dependent on a network connection. In a city, this is fine, in the boonies, not so good.
What is your experience of the evolution of music playback in the car? Similar to mine or different? How so? Feel free to share you experience with solutions that worked for you.