MILESTONES IN THE HISTORY OF THE WEB
Starting point
I'd say the web actually started in 1989 at CERN in Geneva, Switzerland by Sir Time Berners-Lee.
Most important breakthrough
The thing that really made the World Wide Web workable was the invention of the Universal Resource Identifier, which includes the Uniform Resource Locator (URL). This invention is what allows you to type in my.tri-c.edu and see the web page from any browser in the world. When you type my.tri-c.edu into your web browser the request is sent to a Domain Name System (DNS) server if the site is not cached in your browser. The Domain Name Server is like a phone book that matches the web site name with the IP (internet protocol) address of the physical server that hosts the site you are trying to reach. Once the site's IP address is found you are able to retrieve the web site's pages from the hosting server. For more information on how a DNS server works see this web site.
Most important person
The person who contributed the most to the Web as we know it was Tim Berners-Lee because he is the father of the web because he was responsible for suggesting the marriage between the internet and hypertext (this would later become HTML). Prior to the invention of web browsers the internet was primarily used for newsgroups and FTP and was purely text based. Berners-Lee created the worlds first web browser and web server, which was initially text based. Although when he first made his software publicly available it was not very popular, further advancements and interest in the technology allowed the creation of Mosaic in 1993 by Mark Andreessen (Founder of Netscape) and Eric Bina at the University of Illinois at Urbana-Champaign. Mosaic was the first graphical and text based browser and was better than the alternative Gopher at the time because it was free and it included both text and graphics. Most people credit Mosaic with the true birth of the world wide web as we know it today, however I feel Tim Berners-Lee was most important because the original idea was his. More information on Tim Berners-Lee can be found here.
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