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Invented by Joseph Jacquard, this loom was first demonstrated in 1801. It uses punched cards to automatically weave a pattern. Though it is very low tech compared to modern computers, it was still a milestone.
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This computer was the first computer to be at all programmable. It was used by the British to decipher messages being transmitted during World War II. It is a milestone because it was the first computer that could be programmed to do different tasks (ie: deciphering different codes).
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The APL language is one of the earliest programming languages. Invented by Kenneth Iverson, this language started out as an idea in a book, and later went on to become a programming language.
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Microprocessors were first used in calculators, using binary coded decimal. This is a milestone because microprocessors are an essential part of computers today, making them very important.
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The Osborne 1 was the first portable computer. It had a tiny screen, very little memory, and it was really freaking expensive. Despite all this, it remains a milestone, simply because it was the first time that people could take a computer around with them.
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The first Windows software to actually become popular, Windows 2.0 was a 16 bit GUI based operating system that allowed users to have multiple programs open and showing at the same time, unlike the original Windows 1. This is a milestone because it was the beginning of one of the best operating systems to date.