Weirdest thing(s) you had to work with?

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For me:
Vignette (Enterprise CMS from C|NET scripted in TCL)
A distributed data processing system (Map reduce, sharded data storage, Gearman for parallel processing) written using Cake PHP (WTF???)

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First full-time programming job back in the 90s used this:

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My first job out of college was working for a company that wrote hospital financial systems.

The language we used was CADOL. This is an example with a good explanation of the language.

By the time I worked there, it didn’t run on the original hardware, but a virtual environment written in C which ran on AIX.

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