Lots of other people have commented on why Python won in general. I can say why Python was a better choice for me personally, in 1997 or so... I was using Perl

Lots of other people have commented on why Python won in general. I can say why Python was a better choice for me personally, in 1997 or so... I was using Perl a lot to manage an multi-thousand page external site, and a much larger internal site for a major division of a large aerospace/engineering company. These ware all scripts to run on the filesystem to do things like change the company name across thousands of pages, where the historical would be kept for past events, but the new company name would be used for current projects. I sort of semi-nepotisticaly lucked into the job-- I was doing desktop publishing previously, and one of the managers at the division was a relative of my girlfriend. There also were very few webmasters around, and I had a lot of experience with graphics and the software around it.So I taught myself HTML, some basic programming, and was off to the races. But I was basically a just "computer person", but not much of a programmer. Doing anything by hand on a site that big was just not going to happen, and Perl had a bunch of great pre-made scripts available for doing lots of stuff, but it was murder trying to modify any of them. It was clear that Perl just was too much work to learn, and the "one way" philosophy of early Python made the documentation easier, examples more consistent, etc... But Python was much more approachable. It was also pretty clear that it had a better future, and had a pretty good (not great) set of libraries available, pretty good regular expressions, and really good integration with just about anything on Windows 95 (via an external COM library). When I started I didn't realize how the ability to script I.E., or Excel, or whatever was a really powerful tool that saved me countless hours. For example, of of the Marketing execs wanted to review every web page, but didn't want to use a browser, so via Python's COM tools, I could script IE to open, log, and print every page. When something failed (e.g. printer ran out of paper) I could use the log to restart wherever I needed. I could also grab a bunch of data from an Excel workflow some engineer had cooked up and dump all the data into a database, so they could use the tools that were comfortable for them, and still centralize it enough to generate dashboards or reports or whatever for management. The performance wasn't that great, but computers were getting better, faster, all the time, and programmer productivity was starting to become much more of a concern.