A sensible person would've probably used something like a PS1 fat with a SIOCONS cable, to boot executables straight into the console's RAM. But I have no fat PS1, and I'm no sensible person

So first idea was "hey, maybe I could do something with an Arduino". Did it, much like what ackerman did (except I was unaware of his project), and then "hey, how far can I simplify this?". And this is what I ended up with.
That ominous "M" (for "monitor") is a small, 1KB monitor code written in pure assembly. It that talks over the controller ports, and it needs no Arduino or any special part. All you need is a regular, off-the-shelf 3V USB-UART adapter, a controller cable, and a singular 1N4148 diode.
Since it can be launched from either a CD-R or FreePSXBoot, this project is thus fully capable of working on either a fat PS1, a slim PSone, and highly likely also every PS2 console. It works also at a very snappy 115200 bps, so you get a total of 11.5KB/s of throughput for loading binaries on the console's RAM.
The computer-side part of things is a very small Python library which is capable of reading, writing and executing from arbitrary memory locations, and load and execute PS-X EXE files. The protocol is really simple, so it can be implemented also in any other language you can prefer.
Available at: https://github.com/socram8888/joymon