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iirc, Gmail heralded the arrival of β€œAjax” and kickstarted the age of interactive web apps. Everyone and their dog had an β€œRIA” - Rich Internet Application toolkit to sell.
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I think around 1995-96 with cgi-perl scripts for comments sections in ezines for basic "interactivity" but for all the visual jazz, I'd say it became available with javascript coming of age around 2007 though it took designers 4-5 years to master the idiom
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did a thread touching on this recently
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The boundary between Web1 and Web2 was so subtle and incremental most people outside of tech didn’t even notice when it was crossed: when IE7 supported XmlHttpRequest in 2008, paving the way for rich UIs, JavaScript supremacy starting with jQuery, and what was then called Ajax.
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There’s a lot of interactivity in between those extremes, and I’d argue that the web was interactive very early on, and the pre-web internet (with Usenet, BBSs, etc.) were extremely interactive. Phpbb and vbulletin first came out in 2000, BBCode was 1998 and Blogger 1999.
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