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Which cross platform scripting language should we adopt for a group of DBAs?

I wanted to get the community's feedback on a language choice our team is looking to make in the near future. We are a software developer, and I work in a team of Oracle and SQL Server DBAs supporting a cross platform Java application which runs on Oracle Application Server. We have SQL Server and Oracle code bases, and support customers on Windows, Solaris and Linux servers.
Many of the tasks we do on a frequent basis are insufficiently automated, and where they are, tend to be much more automated via shell scripts, with little equivalent functionality on Windows. Unfortunately, we now have this problem of redeveloping scripts and so on, on two platforms. So, I wish for us to choose a cross platform language to script in, instead of using Bash and awkwardly translating to Cygwin or Batch files where necessary.
It would need to be:
Dynamic (so don't suggest Java or C!)
Easily available on each platform (Windows, Solaris, Linux, perhaps AIX)
Require very little in the way of setup (root access not always available!)
Be easy for shell scripters, i.e. DBAs, to adopt, who are not hardcore developers.
Be easy to understand other people's code
Friendly with SQL Server and Oracle, without messing around.
A few nice XML features wouldn't go amiss.
It would be preferable if it would run on the JVM, since this will almost always be installed on every server (certainly on all application servers) and we have many Java developers in our company, so sticking to the JVM makes sense. This isn't exclusive though, since I know Python is a very viable language here.
I have created a list of options, but there may be more: Groovy, Scala, Jython, Python, Ruby, Perl.
No one has much experience of any, except I have quite a lot of Java and Groovy experience myself. We are looking for something dynamic, easy to pick up, will work with both SQL server and Oracle effortlessly, has some XML simplifying features, and that won't be a turnoff for DBAs. Many of us are very Bash orientated - what could move us away from this addiction?
What are people's opinions on this?
thanks!
Chris

You can opt for Python. Its dynamic(interpreted) , is available on Windows/Linux/Solaris, has easy to read syntax so that your code maintenance is easy. There modules/libraries for Oracle interaction and various other database servers as well. there are also library support for XML. All 7 points are covered.

I think your best three options are Groovy, Python, and Scala. All three let you write code at a high level (compared to C/Java). Python has its own perfectly adequate DB bindings, and Groovy and Scala can use ones made for Java.
The advantages of Python are that it is widely used already, so there are tons of tools, libraries, expertise, etc. available around it. It has a particularly clean syntax, which makes working with it aesthetically pleasing. The disadvantages are that it is slow (which may not be an issue for you), untyped (so you have runtime errors instead of compile-time errors), and you can't really switch back and forth between Jython and Python, so you have to pick whether you want the large amount of Python stuff, or the huge amount of Java stuff, minus a lot of the nice Python stuff.
The advantages of Groovy are that you know it already and it interoperates well with Java libraries. Its disadvantages are also slowness and lack of static typing. (So in contrast to Python, the choice is: do you value Python's clean syntax and wide adoption more, or do you value the vast set of Java libraries more in a language made to work well in that environment?)
The advantages of Scala are that it is statically typed (i.e. if the code gets past the compiler, it has a greater chance of working), is fast (as fast as Java if you care to work hard enough), and interoperates well with Java libraries. The disadvantages are that it imposes a bit more work on you to make the static typing work (though far, far less than Java while simultaneously being more safe), and that the canonical style for Scala is a hybrid object/functional blend that feels more different than the other two (and thus requires more training to use at full effectiveness IMO). In contrast to Groovy, the question would be whether familiarity and ease of getting started is more important than speed and correctness.
Personally, I now do almost all of my work in Scala because my work requires speed and because the compiler catches those sort of errors in coding that I commonly make (so it is the only language I've used where I am not surprised when large blocks of code run correctly once I get them to compile). But I've had good experiences with Python in other contexts--interfacing with large databases seems like a good use-case.
(I'd rule out Perl as being harder to maintain with no significant benefits over e.g. Python, and I'd rule out Ruby as being not enough more powerful than Python to warrant the less-intuitive syntax and lower rate of adoption/tool availability.)

The XML thing almost calls for Scala. Now, I love Scala, but I suggest Python here.

If you want a dynamic language and there already a lot of Java developers in your company, then Groovy seems an obvious choice, as it's very easy for Java developers to pick up (also, you said you have some Groovy experience yourself).
Groovy runs on the JVM and has excellent support for working with XML. It also has provides a very straightforward syntax for working with relational databases.
It comes with a console and a shell (though I never use the shell) which make it really easy to test/run scripts or snippets of Groovy code.

Although I prefer working on the JVM, one thing that turns me off is having to spin up a JVM to run a script. If you can work in a REPL this is not such a big deal, but it really slows you down when doing edit-run-debug scripting.
Now of course Oracle has a lot of Java stuff where interaction moght be needed, but that is something only you can estimate how important it is. For plain Oracle DB work I have seen very little Java and lots fo PLSQL/SQL.
If your dba now do their work in bash, then they will very likely pickup perl in a short time as there is a nice, logical progression path.
Since ruby was designed to be an improved version of perl, it might fit in that category too. Actually python also.
Scala is statically typed like Java, albeit with much better type inference.
My recommendation would be to go the Perl route. The CPAN is its ace in the hole, you do not have to deal with the OO stuff which might turn off some DBA's (although it is there for the power users).

I've been in a similar situation, though on a small scale. The previous situation was that any automation on the SQL Server DBs was done with VBScript, which I did start out using. As I wanted something cross-platform (and less annoying than VBScript) I went with Python.
What I learnt is:
Obviously you want a language that comes with libraries to access your databases comfortably. I wasn't too concerned with abstracting the differences away (ie, I still wrote SQL queries in the relevant dialect, with parameters). However, I'd be a bit less happy with PHP, for example, which has only very vendor-specific libraries and functions for certain databases. I see it's not on your list.
THE major obstacle was authentication. If your SQL Server uses Windows domain authentication, you'll have to work to get in. Another system also had specific needs as it required RSA tokens to be supported.
For the second point, Python is quite versatile enough to work around the difficulties, but it was getting into "badly supported" territory, especially on Windows. It was easy to work around the first problem from a Windows host, and for a Unix host it is possible though not easy. If you're using SQL Server authentication, it becomes a lot easier.
From your other choices, I'd expect various ways of authenticating and DB drivers to exist for Perl, which philosophically would be easier for DBAs used to shell scripting. Ruby - no experience, but it tends to have spotty support for some of the odder authentication methods and connectors. Scala I'd expect to be a bit too much of a "programmer's programming language" -- OOO and FP? It's a very interesting language, but maybe not the one I'd chose at first. As for the rest of the Java-based options, I don't have an opinion, but do check that all the connection types you want to make are solidly supported.

Standardizing a Release/Tools group on a specific language

I'm part of a six-member build and release team for an embedded software company. We also support a lot of developer tools, such as Atlassian's Fisheye, Jira, etc., Perforce, Bugzilla, AnthillPro, and a couple of homebrew tools (like my Django release notes generator).
Most of the time, our team just writes little plugins for larger apps (ex: customize workflows in Anthill), long-term utility scripts (package up a release for QA), or things like Perforce triggers (don't let people check into a specific branch unless their change description includes a bug number; authenticate against Active Directory instead of Perforce's internal passwords). That's about the scale of our problems, although we sometimes tackle something slightly more sizable.
My boss, who is reasonably technical, has asked us to standardize on one or two languages so we can more easily substitute for each other. He's advocating bash scripts and Perl, due to their universality and simplicity. I can see his point--we mostly do "glue", so why not use "glue" languages rather than saddle ourselves with something designed for much larger projects? Since some of the tools we work with are Java-based, we do need to use something that speaks JVM sometimes. (The path of least resistance for these projects is BeanShell and Groovy.) I feel a tremendous itch toward language advocacy, but I'm trying to avoid saying "We should use Python 'cause I like it and Perl is gross."
Instead, I'm trying to come up with a good approach to defining our problem set: what problems do we solve with scripts? Would we benefit from a library of common functions by our team, or are most of our projects more isolated? What is it reasonable to expect my co-workers to learn? What languages give us the most ease of development and ease of modification?
Can you folks suggest some useful ways to approach this problem, both for my own thinking process and to help me facilitate some brainstorming among my coworkers?

Two points:
"Eww Perl gross" is somewhat of an urban legend. You can write great clean self-documenting code in Perl, and your can write write-only code in pretty much any language. It's a property of a developer, not a language.
Just because you're writing glue code, doesn't mean the code has to suck like some glue hacks tend to be.
From many threads comparing Perl vs Python on SO, it appears to me that Perl's CPAN is more expansive than Python's repository, but I have no experience with Python and can't substantiate with real comparison.
BUT, one thing I do know. After 5 seconds search, CPAN has a JIRA module. Whether that's a good factor for you or not, that's up to you.

Google standardized on Python for such tasks (and many more) a bit before I joined the company; as far as I know, huge advantages such as Python's great implementations on the JVM and .NET didn't even play a role in the decision -- it was all about readability. At the time (and to some extent, even now) the theory at Google was that every engineer must be able, at need, to tweak every part of the codebase -- including of course build scripts, spiders (which were in Python at the time), and so forth. Demanding of engineers already proficient in C++ and Java to learn many more "scripting" languages (Python, Perl, Bash, Awk, Sed, and so forth) was simply unconsciounable: one had to be selected. Given that constraint, Python was the clear choice (under other constraints, Perl might also have been -- but I can't see the inevitable mix of Bash, Awk and Sed ever competing on such grounds!_) -- and that's how I ended up working there, a bit later;-).
Given that the overall potential of Python vs Ruby vs Perl vs PHP vs Bash + Awk + Sed vs ... is roughly equal, picking one is clearly a winner -- and Python has clean readability, strong implementations on JVM and .NET as big vigorishes. Seriously, I can only think of Javascript (inevitable for client-side work, now rich with strong implementations such as V8) as a possible "competitor" (unfortunately, JS inevitably carries on a lot of baggage for backwards compatibility -- unless you can use a use strict;-like constraint to help on that, it must be an important downside).

I don't think anyone is going to be able to solve your problem on Stackoverflow. Your choice of tools, methods, and process are much more affected by social constraints, e.g. what your boss wants and what you want, then technical merits. That's not necessarily bad.
The short answer is "Use what is going to be most pleasing to the developers". If everyone likes Python more than Perl, for whatever reason, they are probably going to get more done in Python. If they like Ruby more than Python, it's the same thing.
Some things to evaluate as part of your selection:
What do the developers already know?
What are they most willing to learn?
How much weekly time can your team spend learning new things (e.g. lunch seminars, formal classes, etc)?
What do most people in the community use to work with the tool you need to support? For instance, Fisheye has a Java API, and some REST examples for Perl and Python. If you're writing Fisheye extensions, Java seems to be the win there. If you're merely accessing Fisheye data, any language can use the REST stuff.
What is most of your code base in already? What can you replace and what do you have to continue to support? I find that many companies can't answer this question because every developer seems to add two new technologies they don't tell anyone about. :)
Which platforms do you need to support? Some languages have platform specific issues, and I don't mean just Windows vs. Unix. Do you have legacy hardware you have to support? Does your tool work on that stuff?
How much of the stuff you produce can benefit other parts of the company? What are other teams using?
Do the people advocating one tool know it well enough to be its champion? I ask What are five things he hate about your favorite language? If people can't name five valid things that are wrong with their language or tool, they don't have enough experience with it.
The Longer Answer
People tend to try to reduce this to a technical argument because they are afraid to admit their biases or examine why they think what they think. Your boss might favor bash and Perl because that's what he did a lot of work in when he was getting started. You might like Python because you have a personal affinity for the way Python does things. I like Perl because I like its flexibility and DWIMmery. Like any social situation, different people are going to be attracted to different parts of different things. Just because you like chocolate doesn't make vanilla evil. I could give you lots of good arguments why Perl can be useful, but that doesn't mean that something else can't give you the same value.
What problems do we solve with scripts?
That one you have to answer for yourself. :)
Would we benefit from a library of common functions by our team, or are most of our projects more isolated?
This is most likely a good thing in Python, Perl, Ruby, Java, and almost any other language that you might choose. I think this part of your requirement is language agnostic. No matter which one you choose, you'll probably want to do this.
What is it reasonable to expect my co-workers to learn?
A good developer should be able to work with several different languages at least to an apprentice level. Those languages should include ones that have vastly different assumptions about how people express problems, say, for example, the set { Smalltalk Perl C Lisp Java }.
The best developers I've hired and worked with have always wanted to use the right tool for the job instead of making the job right for the tool. They might have their favorite language, but they didn't grouse (too much) about using a different tool when it made more sense.
Many "developers", however, seem to think that they are getting paid to play with their favorite tool. You need to convert them into people who think they have a toolbox to solve problems that create business value.
And remember, you never stop learning. As a developer you don't have to choose one language then defend it with your life, forsaking all others, in sickness and in health, and so on. Good developers are going to continue to track new technologies and evaluate them for usefulness for their tasks. Just because you choose one tool over another doesn't mean you stop paying attention.
No matter what you choose, someone is going to complain. Don't look for the solution that makes everyone happy. There isn't one, short of getting rid of the developers who aren't happy.
What languages give us the most ease of development and ease of modification?
A skilled practitioner in just about any language will think that his chosen language is the easiest to develop, modify, and maintain. Unskilled practitioners tend to blame the language and the tools for their problems. Some languages have steeper learning curves, and some have bigger payouts. A person's tolerance with immediate gratification is a big factor here.
That being said, different languages have developed different cultures and different toolsets. Perl people tend to like vi or emacs, Ruby people tend to like TextMate, Java people tend to like Eclipse or IntelliJ. That's not always true, but the culture that evolves around the tools are often more important than the technical details of the tool. If your developers like a particular type of tool, they are probably going to like the language that has a culture built around that sort of tool.
Some processes and tools take more time to get used to or require more education, but they can have larger advantages when used properly. Other tools get you started sooner but might not give you a path to bigger and greater things, such as cross-team development. The trick, however, is to not code to the tools so you aren't stuck in any particular toolset.

First, it's important to note that it is very hard to convince someone they're wrong.
He's advocating bash scripts and Perl,
due to their universality and
simplicity
Bash scripts are not simple. The bash programming model is really complex and unfriendly. if statements and expressions, in particular are horrifying.
Perl may or may not be simple.
Bash is universal. Perl, however, is exactly as universal as Python. Python is pre-installed in almost all Linux distributions. So that argument is specious.
The "universality" of bash, Perl and python is exactly the same. The "simplicity", however, is not the same. You won't find it easy to to "prove" or "convince" anyone of this once they've already pronounced Perl as simple.
The Situation.
If the boss is advocating Perl, and Perl is not the answer, you will find it is very hard to convince someone they're wrong, making this effort nearly impossible.
If the boss was just throwing out ideas, then this is just difficult.
Quick Hack.
An easy thing you can do is to attempt head-to-head comparisons of Python and Perl for some randomly-chosen jobs. You can then have a code walkthrough to demonstrate the relative opacity of Perl compared with the relative clarity of Python.
Even this is fraught with terrible dangers.
Some folks really think code golf is important. Python loses at code golf. Perl wins. There's nothing worse than "Angry Co-worker with Perl Bias" who will kill you with code-golf solutions that -- because they're smaller -- can baffle management into thinking that they're clearer or "better" on some arbitrary scale.
Some folks really think explicit is "wordy" and bad. Python often loses because the assumptions are stated as actual parameter values. Some folks can (and do) complain at having to actually write things down. Read Stack Overflow for all of the Python questions where someone wants to make the try: block go away in a puff of assumptions.
If you choose random problems, you may -- accidentally -- chose something for which there's an existing piece of Perl or Python that can be downloaded and installed. A language can win just through an accident of the draw. Rather than a more in-depth comparison of language features.
Best Bet
The best you can do is the following.
Identify what folks value. You can call these "non-functional" requirements. These are quality factors. What are the foundational, core principles? Open, Accessible, Transferrable Skills, Simplicity, Cleanliness, Honesty, Integrity, Thriftiness, Reverence, Patience, Hard Work, A Sense of Perspective, Reef the Main in Winds over 20 kn, etc. This is hard. No sympathy here.
Identify the technical use cases. These are "functional" requirements. Which bits of glue and integration there are? This is hard, also. Requirements erupt of out of the woodwork when you do this. Also, when you have a Perl bigot on the team, numerous non-functional requirements will pile into this area. Your manager -- who proposed Perl -- may be the Perl bigot, and the use cases may be difficult to collect in the presence of a Perl bigot.
Identify how (a) Perl + Bash vs. (b) Python vs. (c) Java fit this core values and the functional requirements. Note that using Python means you do not need to use Bash as much. My preference, BTW, is to pare Bash down to the rock-bottom minimum.
This is a big, difficult job. It's hard to short-cut. If you find that Perl is not the answer and the Perl bigot you need to convince is the manager who proposed Perl in the first place, you may find that convincing someone that they're wrong is very hard.
Edit. I am aware that I am forbidden from using the string "Perl Bigot" to describe the manager's potential level of bias toward Perl. I, however, insist on using "Perl Bigot" to describe the manager who proposed Perl. The question provides no information on which to change this. The worst case is that (a) the manager is the Perl Bigot and (b) Perl is not the answer.

Python -- what is NOT in 2.7 that IS in 3.1? So many things have been back-ported, what is NOT?

I've been following the saga of Python 3.x and have watched the 3.x features gradually getting back-ported to the 2.x line.
Most of the libraries I use haven't been ported and some (e.g. Twisted) seem covertly or overtly hostile to 3.x to varying degrees. At any rate, there has been very little movement towards compatible versions of many of them. Expecially the larger ones.
So, my question is, with all the features that have been backported, what is still available in 3.x that's NOT been back-ported? It's pretty easy to find what has been backported, but not what's left.
Right now, porting to 3.x just seems like all pain, and I can't see the gain; maybe an "Only in 3.x" list would let me see the light...
Thanks,
Stu

The most important thing is probably unicode throughout. So there is no need anymore to fiddle around with str/unicode. This sounds small but has huge (positive) implications when you think of OS interaction - for example everyone has to try hard to give you 'usable' strings instead of 'a binary thing that might be an error message'.
There's also a lot of stuff in the interpreter itself that was improved. One example is the global interpreter lock (GIL) which did not vanish but it way better in py3k: presentation+slides

Speed might be a feature worth mentioning.
The speed imporovements of project "Unladen Swallow" have been approved to be merged into Python. But as far as I know only to Python 3. See PEP 3146 for details.

I'm a .NET Programmer. What are specific uses of Python and/or Ruby for that will make me more productive?

I recall when I first read Pragmatic Programmer that they suggested using scripting languages to make you a more productive programmer.
I am in a quandary putting this into practice.
I want to know specific ways that using Python or Ruby can make me a more productive .NET developer.
One specific way per answer, and even better if you can say whether I could use Python or Ruby or Both for it.
See standard format below.

IronPython / IronRuby
IronPython in Action will do a better job explaining this (and exactly how best to use IronPython) that can possibly be accommodated in a SO answer. I'm biased -- I was a tech reviewer and am a friend of one of the authors -- but objectively think it's a great book. (No idea if IronRuby is blessed with a similarly wonderful book, yet).
As you want "one specific way per answer" (incompatible with SO, which STRONGLY discourages a poster posting 25 different answers if they have 25 "specific ways" to indicate...!-): prototyping in order to explore some specific assembly or collection thereof that you're unfamiliar with (to check if you've understood their docs right and how to perform certain tasks) is an order of magnitude more productive in IronPython than in C#, as you can explore interactively and compilation is instantaneous and as-needed. (Have not tried IronRuby but I'll assume it can work in a roughly equivalent way and speed).

Less Code
I think productivity is direct result on how proficient you are in a specific language. That said the terseness of a language like Python might save some time on getting certain things done.
If I compare how much less code I have to write for simple administration scripts (e.g. clean-up of old files) compared to .NET code there is certain amount of productivity gain. (Plus it is more fun which also helps getting the job done)

Advanced Text Processing
Traditional strengths of awk and perl. You can just glue together a bunch of regular expressions to create a simple data-mining system on the go.

Learning a new language gives you knowledge that you can bring back to any programming language. Here are some things you'd learn.
Add functionality to your objects on the fly.
Mix in modules.
Pass a chunk of code around.
Figure out how to do more with less code: ruby -e "puts 'hello world'"
C# can do some of these things, but a fresh perspective might bring you one step closer to automating your breakfast.

Embedding a script engine
Use of IronPython for a scripting engine inside your .NET application. For example enabling end-users of your application to change customizable parts with a full fledge language such as Python.
A possible example might be to expose custom logic to end-users for a work flow engine.

Quick Prototyping - Both
In the simplest cases when firing a python interpreter and writing a line or two is way faster than creating a new project in visual studio.
And you can use ruby to. Or lua, or evel perl, whatever. The point is implicit typing and light-weight feel.

Cross platform
Compared to .NET a simple script Python is more easily ported to other platforms such as Linux. Although possible to achieve the same with the likes of Mono it simpler to run a Python script file on different platforms.

Processing received Email
Python has built-in support for POP3 and IMAP where the standard .NET framework doesn't. Useful for automating email triggered tasks.

Python 3.0 and language evolution

Python 3.0 breaks backwards compatibility with previous versions and splits the language into two paths (at least temporarily). Do you know of any other language that went through such a major design phase while in maturity?
Also, do you believe that this is how programming languages should evolve or is the price to pay simply too high?

The only language I can think of to attempt such a mid-stream change would be Perl. Of course, Python is beating Perl to that particular finish line by releasing first. It should be noted, however, that Perl's changes are much more extensive than Python's and likely will be harder to detangle.
(There's a price for Perl's "There's More Than One Way To Do It" philosophy.)
There are examples like the changes from version to version of .NET-based languages (ironic, considering the whole point of .NET was supposed to be API stability and cross-platform compatibility). However, I would hardly call those languages "mature"; it's always been more of a design-on-the-go, build-the-plane-as-we-fly approach to things.
Or, as I tend to think of it, most languages come from either "organic growth" or "engineered construction." Perl is the perfect example of organic growth; it started as a fancy text processing tool ala awk/sed and grew into a full language.
Python, on the other hand, is much more engineered. Spend a bit of time wandering around the extensive whitepapers on their website to see the extensive debate that goes into every even minor change to the language's syntax and implementation.
The idea of making these sorts of far-reaching changes is somewhat new to programming languages because programming languages themselves have changed in nature. It used to be that programming methodologies changed only when a new processor came out that had a new instruction set. The early languages tended to either be so low-level and married to assembly language (e.g. C) or so utterly dynamic in nature (Forth, Lisp) that such a mid-stream change wouldn't even come up as a consideration.
As to whether or not the changes are good ones, I'm not sure. I tend to have faith in the people guiding Python's development, however; the changes in the language thus far have been largely for the better.
I think in the days to come the Global Interpreter Lock will prove more central than syntax changes. Though the new multiprocessor library might alleviate most of that.

The price of insisting on near-absolute backwards compatibility is just too high. Spend two minutes programming in C++ if you want to see why.

The python team has worked very hard to make the lack of backward compatibility as painless as possible, to the point where the 2.6 release of python was created with a mind towards a painless upgrade process. Once you have upgraded to 2.6 there are scripts that you can run that will move you to 3.0 without issue.

It's worth mentioning that backward compatibility incurs costs of its own. In some cases it's almost impossible to evolve a language in the ideal way if 100% backward compatibility is required. Java's implementation of generics (which erases type information at compile-time in order to be backwardly-compatible) is a good example of how implementing features with 100% backward compatibility can result in a sub-optimal language feature.
So loosely speaking, it can come down to a choice between a poorly implemented new feature that's backwardly compatible, or a nicely implemented new feature that's not. In many cases, the latter is a better choice, particularly if there are tools that can automatically translate incompatible code.

I think there are many examples of backward compatibility breakages. Many of the languages that did this were either small or died out along the way.
Many examples of this involved renaming the language.
Algol 60 and Algol 68 were so different that the meetings on Algol 68 broke up into factions. The Algol 68 faction, the Pascal faction and the PL/I faction.
Wirth's Pascal morphed into Modula-3. It was very similar to pascal -- very similar syntax and semantics -- but several new features. Was that really a Pascal-2 with no backward compatibility?
The Lisp to Scheme thing involved a rename.
If you track down a scan of the old B programming language manual, you'll see that the evolution to C looks kind of incremental -- not radical -- but it did break compatibility.
Fortran existed in many forms. I don't know for sure, but I think that Digital's Fortran 90 for VAX/VMS wasn't completely compatible with ancient Fortran IV programs.
RPG went through major upheavals -- I think that there are really two incompatible languages called RPG.
Bottom Line I think that thinking and learning are inevitable. You have three responses to learning the limitations of a language.
Invent a new language that's utterly incompatible.
Incremental chagne until you are forced to invent a new language.
Break compatibility in a controlled, thoughtful way.
I think that #1 and #2 are both coward's ways out. Chucking the old is easier than attempting to preserve it. Preserving every nuanced feature (no matter how bad) is a lot of work, some of it of little or no value.
Commercial enterprises opt for cowardly approaches in the name of "new marketing" or "preserving our existing customers". That's why commercial software ventures aren't hot-beds of innovation.
I think that only open-source projects can be embrace innovation in the way that the Python community is tackling this change.

C# and the .NET framework broke compatibility between versions 1.0 and 1.1 as well as between 1.1 and 2.0. Running applications in different versions required having multiple versions of the .NET runtime installed.
At least they did include an upgrade wizard to upgrade source from one version to the next (it worked for most of our code).

Wouldn't VB6 to VB.net be the biggest example of this? Or do you all consider them two separate languages?

In the Lisp world it has happened a few times. of course, the language is so dynamic that usually evolution is simply deprecating part of the standard library and making standard another part.
also, Lua 4 to 5 was pretty significant; but the language core is so minimal that even wide-reaching changes are documented in a couple of pages.

Perl 6 is also going through this type of split right now. Perl 5 programs won't run directly on Perl 6, but there will be a translator to translate the code into a form that may work (I don't think it can handle 100% of the cases).
Perl 6 even has its own article on Wikipedia.

First, here is a video talk about the changes Python will go through.
Second, changes are no good.
Third, I for one welcome evolution and believe it is necessary.

gcc regularly changes how it handles C++ almost every minor release. Of course, this is more a consequence of gcc tightening how they follow the rules, and less of C++ itself changing.

The new version of the Ruby programming language will also break compatibility.
And think of the libraries one might use: gtk, Qt, and so on (they also have incompatible versions).
I think incompatibility is necessary sometimes (but not too often) to support progress.