Looking to confirm the other way around though - data sent to a 1/8 jack, but converted to analog audio without a chipset or anything.
Nope.
In the USB to audio setup, a resistor in the cable or adapter indicates to the device that it should switch the use of the USB connector to analog audio instead of USB data. So, when you plug in your headset you do indeed get analog audio. There's no way for your standard audio headphones with a 2.5 or 3.5 mm audio plug to use
data from the USB connector.
For this to work, the phone or other device has to have hardware and software support for the CEA-936-A standard. Then it can switch between USB data, audio or a couple of different charging standards using the same USB connector. I didn't dig deep enough to see how the charging standards differ.
It's a pretty slick little standard, and will let you design a product with one less expensive, failure-prone connector.
Now, having said that... the world is full of devices that have used round audio plugs (1/4", 1/8", 2.5mm; mono, stereo and 4-conductor) for both audio and data. Yaesu does it on their handhelds, as do several other manufacturers. Usually you get either audio, or serial data - depending on the mode you're in. And as mentioned before, TI used a 3.5mm plug for data transfer for a long time, probably because it was smaller and cheaper than anything else. Some use actual serial TTL, CMOS or RS232 level data; a few use AFSK audio like a modem.
Even the headphones and headsets you see with USB connectors are not really converting data to sound directly. They are USB sound devices that connect to your PC as such, take USB digital data packets and convert them to sound with a CPU and DAC and numerous layers of software. It wouldn't surprise me to see one with an adapter and some way to bypass all the USB stuff and plug them into your MP3 player, but none of the ones I have seen had such adapter.