3 potential solutions:

• USB - apple 30 pin: note that the pin number might change depending on release year. Someone smarter than me will mention why firmware might not work out.
• USB to aux: this will give you a headphone jack and is the most reliable
• FM transmitter: if you lack a headphone jack you can also get an FM transmitter. It makes your device a mini radio station. These are pretty unreliable or staticy, but sometimes you need an option. I would recommend a new player first.

“probably won’t remember”?

Man. Fuck this kid. I’m not that old…

Everyone in these comments are idiots? Or bots? Usb to aux outputs, Bluetooth to aux outputs guys it’s a freaking iPod the one thing it has is aux output. The problem is getting it into the radio.

Op, does your radio have aux in? That’s the easiest but it’s so simple I think you would have done it already.

If you don’t sometimes you can buy an adapter that plugs into the back of your radio, heck eBay might net you an actual iPod 30 pin cable specific to your radio.

If your radio has Bluetooth, you can get an aux Bluetooth transmitter not reciver like people linked here, to transmit from the headphone jack to your radio.

Last resort is a fm transmitter with either aux or a 30 pin.

Male to male aux, if your car has aux input. Maybe aux to fm (like this), so you can connect ipod to the transmitter, then set the car’s radio to the same frequency.

We should start with, what car do you have? Then we can figure out if it has an AUX port.

Also if this Nano has an original battery, you might want to replace it before it becomes bloated.

The more usual thing are aux to USB adapters but they can only do USB to aux, nit the reverse. What you need is aux to USB converter, they can do both ways.

This article is good, autotranslate if not german.

There are AUX cables that have a transmit and recive switch. You can use this to transmit the output of your iPod through AUX to a built in bluetooth receiver in your car or other device.

https://www.amazon.co.uk/UGREEN-Bluetooth-Transmitter-Headphone-Connection/dp/B0D12MFCBG

Just make sure what you choose has the transmitter function as most cheaper ones only have the receiver function (for use in a car stereo for example).

It is likely the car USB port is looking through directories for MP3 files, and thats not now those iPods present themselves when hooked up via USB. You might be able to find an audio-to-bluetooth adapter, but it is likely you will not be able to control the device through the car’s interface, so you would have to press play manually.

(Side note: older cars with USB might have a very low-level relationship with the USB sticks, where they read files in the order they were written to the device, without regard to what folders you put them in. There are utilities that can reorder the files’ physical position on the stick so that albums play in order)

The USB port in your car radio might only support a specific file format for the drive (like EXT, FAT32, NTSF) that the iPod doesn’t use (IIRC, the iPod used Fat32 or Fat16?)

Or it doesn’t see directories and would work with a plain USB stick loaded with .MP3s loosely added to it. You could get a iPod to do this, but it wouldn’t work as an iPod anymore; it would be an external hard drive.

Does the radio have a 3.5mm AUX jack? If so, just use that.

I’ve had one of those (battery died, unfortunately) and if you’d look at its files, you’d notice that they are organized in a different structure than what an MP3 player might expect.

iPod_Control\Music’s sudirectories might contain some songs, but the filenames are hashes (corresponding to the entry in the iPod db). The metadata and the contents are perfectly fine, and you can play the file yourself via a different player (you can probably test it in your computer).

I suggest you just connect the iPod through the 3.5mm output audio jack or find a 3.5mm audio output to Bluetooth transmitter adapter.

EDIT:

WTF. I triple posted. My bad. I deleted the two others, also corrected some minor typos and mistakes.

Back in the day, I had one of the fm transmitters wired into the antenna with a ground loop isolator from radio shack (!) and I tapped a power lead so it would also charge my iPod while in use (and automatically turn off the power when the car was off). Honestly, it was awesome. CD quality sound. If I remember correctly Belkin made the transmitter.

Further to the other answers; I have one of these for using my iPod in the car. It has the added bonus of taking line-level volume, so you set the volume from the head unit, not the iPod. And it can charge while you’re using it.

I think it’ll charge from the head unit’s USB socket without trying to connect, because the USB plug is just for charging.

Are you sure your car doesn’t have an aux in? Most cast do. Otherwise, maybe a USB to aux converter might work but I doubt it. So I’d go with a Bluetooth or FM transmitter like others adviced. If your car has Bluetooth, I’d go for that one as FM can have interference. Or just play music from your phone. No iTunes hassle and more storage.

Seperate from the FM transmitters that other people have mentioned, you can install an FM modulator into your car. This is a box that goes behind your stereo, feeds power off the stereo power supply, and connects directly to the antenna wire to supply the frequency modulated sound signal directly to the antenna without traveling through the air. Similar to an FM transmitter, it has a headphone wire that plugs into the headphone outlet of your ipod for the audio signal. It can bypass the interference problem that FM transmitters run into, but the one I installed back in the day actually picked up engine revving noise from my alternator, so maybe it needed better wire shielding. Obviously this requires taking out your stereo and doing some wiring work so you need some tinkering skills or have it installed by a pro.

The reason the USB plug on your ipod doesn’t work is that earlier audio devices like the original ipod didn’t have a way to transmit audio digitally over USB, it was only used for charging and file transfer.

How old is your car? Ipod support is odd like post 2015.