Knuth's Rage Against the Machine
In 1977, Donald Knuth received galley proofs for the second edition of The Art of Computer Programming and was, in his own word, "horrified." The publishing industry had just abandoned hot-metal Monotype machines for phototypesetting, and the results were ugly: distorted fonts, mangled subscripts, mathematical formulas that looked like they'd been set by someone who had never seen an equation. Knuth, a Stanford computer scientist with the aesthetic sensibilities of a Renaissance typographer, decided to fix the problem himself.
He thought it would take a few months. It took a decade.
What emerged was TeX—a system built on the "boxes and glue" model, where every character is a rectangular box and every space between them is stretchable glue. Where a normal word processor breaks lines one at a time (shoving the overflow to the next line like a careless bricklayer), TeX reads an entire paragraph and solves a global optimization problem to find the arrangement that minimizes ugliness across all lines simultaneously. The result is the eerily uniform "color" of a TeX page—that consistent grayness that typographers prize and most software can't achieve.
The first version, TeX78, was written in Stanford's SAIL language. But Knuth wasn't satisfied with portability, so he rewrote the entire system as TeX82 using his invention of literate programming—a methodology where the source code is the documentation, interleaved in the order a human would explain it. The resulting book, TeX: The Program, remains a masterclass in software engineering four decades later.
The $2.56 Check: Knuth offered a reward of $2.56 (one "hexadecimal dollar") for every bug found in TeX. The amount doubled each year. Almost no one cashed the checks—recipients framed them as trophies. In 2008, Knuth replaced physical checks with certificates from the fictional Bank of San Serriffe.