Patrick Craig tells the story of the $5000 compression challenge, in which a challenge to compress random data was gamed.
HN links it whenever data compression or storing data in metadata comes up, and one commenter ranks it as an excellent computer story.
Here's a mildly amusing challenge and response to that challenge:
(http://www.patrickcraig.co.uk/other/compression.htm)
This page has some nice compression gimmicks (a file that compresses well with one algorithm but hardly at all with another; a file that uncompresses to itself)
(http://www.maximumcompression.com/compression_fun.php)
The large text compression benchmark has some nice finely tuned compression software and statistics.
(http://mattmahoney.net/dc/text.html)
And the Hutter prize is interesting. (Get the 100 Mb file of enwiki8 and the de-compressor to under 16 Mb)
(http://prize.hutter1.net/)
Same problem. The amount of information that you need to specify a compressible offset plus the compressibility of said offset adds up to at least the amount of information you were trying to encode, and no compression happens.
If you ignore either half of the information problem, you can get what looks like compression but really isn't.
See https://www.patrickcraig.co.uk/other/compression.php for a fun story about "data hiding" to show exactly how sneaky the data hiding can be.
Do you mean this - [1]? Yes, this was pretty cool! I esp liked how Mike, the person initiating the bet, initially was super-confident he'd win:
It would be very easy to point out to him the impossibility of his task, but far more interesting to see how long he will struggle with the problem before realizing it for himself.
[1] http://www.patrickcraig.co.uk/other/compression.php
He did not,
full story, for the perspective of the metadata guy is here
https://www.patrickcraig.co.uk/other/compression.htm
Excellent computer story, on a par with "We can't send email more than 500 miles" IMO.
Somewhat off topic, but this reminded me of one of my favorite HN submissions:
Link - http://www.patrickcraig.co.uk/other/compression.php
Previous commentary - https://news.ycombinator.com/item?id=9163782
Reminds me of the infamous compression challenge where one person tried to cheat and win the prize by storing data in filenames: http://www.patrickcraig.co.uk/other/compression.htm