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Update: I've dropped the "2011" from the title, as I've kept this list more or less up-to-date every time I change a computer.
Other than Visual Studio, Photoshop, Office/Outlook, 3dsMax (/Maya/Modo/...) and Perforce, these are the tools that I always have installed on my development computer.
In strikethrough are tools that I used to install / might still be useful, but don't really rely upon anymore (these might go away as I update the list)
I don't use OSX for development at all, but I use it almost exclusively at home for photography and general computer stuff... So I included a few OSX tools too, even if you won't find as much programming stuff.

A good way of installing software in bulk is to use Ninite. On OSX: ZeroInstall or GetMacApps are alternatives.


The opposite, uninstall, is also best served by some bulk/batch tools: Absolute Uninstaller and for Windows 8+ App Uninstaller.
File tools
MUST-HAVE! Everything is by far the tool I use the most. It's life-changing. After installing it I also I limit windows search indexing options only to the start menu and email, as the latter is required by Outlook). Agent Ransack is nice too. MUST-HAVE Beyond Compare is a must for programming. Araxis Merge is also nice to have. Nowadays I'm working more across workstations it's handy to have a faster file copier over the network, I use FastCopy (see http://www.raymond.cc/blog/12-file-copy-software-tested-for-fastest-transfer-speed/) so I can sync Perforce depots (and then use p4 flush) on both machines without going through the p4 server (also, if you have HDD space, use a local p4 proxy, it's nifty!). TeraCopy is similar and has a Mac version too. TreeSize or WinDirStat or similar, but as I don't really need it often, I just get the portable version as needed (OSX: Grand Perspective). MUST-HAVE 7-Zip (OSX: Keka or Zipeg). I found that WinRAR can still be very useful if you need to handle symlinks / hardlinks. Most other compressors don't. TestDisk and Recuva for file recovery. BareTail seems nice. Coding
Visual Studio plugins/extensions MUST-HAVE Extensions (from the VS extension store): Debug Command Line (adds a drop-down that allows to quickly switch between recently used command-lines), Debug Single Thread, Concurrency Visualizer Other minor ones: Indent guides is not bad, I like Continuous formatting as I found auto-formatting to be great but hard to apply in existing codebases. Speaking of which, Clang-Format is powerful and easy, and CodeMaid is very nifty as well. Local History SymbolSort (not really a plugin...) Visual Studio Color Theme Editor I used to rely on Visual Assist X (and disabling Intellisense), but nowadays I just use find in files (SSDs!) most of the times... Text editors MUST-HAVE NotePad++ for almost everything (with this HLSL syntax add-on by Pettineo). MUST-HAVE Sublime Text (OSX too) Markdown editors I still write a lot of plain .txt files, and using markdown gets you some formatting for free. Typora is my choice (OSX too), MarkDeep is nice, Marp can be cute as well (for presentations, there are many other similar ones). LaTeX for publications - I use TexStudio and BasicTeX (a smaller version of MacTeX) on OSX (then manually add packages I need via the command line package manager). Sometimes you need a hex editor (e.g. to open huge files) IDEs. ...Of course, Visual Studio, but you might need stuff for other languages. MUST-HAVE Visual Studio Code is great nowadays (also on OSX) Lua Decoda is a great (now opensource!) IDE if you need one for Lua (which you probably shouldn't). ZeroBrane Studio is good too and integrates a number of game engines (mostly 2d and indie-ish, like Love, Moai, Corona) with a limited "livecoding" support (change of constant parameters) Python Python tools for Visual Studio, PyCharm (OSX too) I like interactive environments like Spyder and IPython/Jupyter, which are included in many "scientific" python distributions. MUST-HAVE  Anaconda is my favorite (OSX too). C# ILSpy is great, as it is NDepend but I use them rarely as I'm not dealing usually with large C# projects. DotPeek sometimes is handy. For most other things (and for OSX...), JetBrains has an IDE. Everybody in videogames is on P4, but the outside world likes GIT too.  TortoiseGIT is good but young, SourceTree is better, also works on OSX Other development tools: Very Sleepy (windows sampling profiler) as in most cases I don't have VTune around. AMD CodeXL is very useful too Include files dependency watcher, Dependency walker Faster "find in files": SilverSearcher / RipGrep ZealDocs offline documentation browser (OSX too). Cheatsheet on Mac is also nifty Sometimes, C++ analysis software  Lattix and VisualC++Depend, compiler/compilers like Antlr, but this is not really part of my daily routine nor of my "default" install CppCheck, OpenCppCoverage Volatility framework and Intel Pin for really nasty stuff Graphics and Rendering
MUST-HAVE IrfanView is my image viewer. Picturenaut, HDRShop and PTGui for HDR images. OSX Alternatives: Xee VisiPics is the best near-duplicate image finder I've found so far. MUST-HAVE RenderDoc is great, a must! ApiTrace is promising, Intel's GPA is ok too. Pyramid ShaderAnalyzer MUST-HAVE VideoLan (OSX too) Also for screen captures! I just use the desktop capture device and encode a mp4. On OSX, the built-in Quicktime allows do to screen recording. Giffing and ScreenToGif are great for desktop capture too (using webM encoding) Giphy capture works wonders as well (and it's on OSX too) Prototyping MUST-HAVE Processing (also on OSX). MUST-HAVE C-Toy (also on OSX). Quite nifty! Tiny-C-Compiler integrated with some graphic drawing functions and wrapped with a file-monitor so your project live updates. Very useful to quickly test C algorithms! SharpDX Unity3D is great for prototypes! KodeLife for shader experiments. (also on OSX) Other stuff MeshLab for 3d stuff. Marmoset Toolbag and cmftStudio which is somewhat similar, but opensource. I hate Gimp but I do use sometimes the portable version if I don't have Photoshop on a given machine. Blender is good now! Desktop
AutoIt is NIFTY! I use it to craft quick GUIs around command-line tools or to automate GUI tools... It's really nice when you have to do a given thing over and over, and its basic-inspired language makes me nostalgic too. Also, is "portable", which I always prefer. AutoHotKey uses AutoIt scripting, but I didn't use it yet. MUST-HAVE OSX I use Alfred MUST-HAVE Acrobat Reader (even if I should probably prefer the less bloated SumatraPDF, that does not annoy the user with endless updates) ProcrastiTracker... Also for "productivity" I like sometimes to use the "pomodoro technique", I have a kitchen timer on my work desk that seems to work best (I like it being physical and ringing), but ChronoSlider on OSX doesn't seem to suck as well (you'd be surprised how bloated or bad most timer apps are...) System tools Unlocker MUST-HAVE Sysinternals tools (ProcMon, FileMon, VMMap, RamMap...) MUST-HAVE CCleaner (now also on OSX) Process Hacker RapidEE (environment variable checker/editor), also portable. NirSoft tools ShutUp10 SharpKeys if I need to remap some of my keyboard keys.  Some keyboards emit "weird" scancodes (e.g. my wired Apple Italian keyboard) the only program which I've found to be flexible enough to recognize them is KeyTweak. Speaking of using Apple hardware, if you have a laptop and you like your natural scrolling direction on the touchpad, WizMouse can enable that.  By the way, Win 8.1/bootcamp on my MBPr2013 does dragging horribly, but it seems better if you enable the (unrelated!) "tap to click" and "dragging" options in bootcamp.  Trackpad++ is also related but I haven't tried it yet - same people do a number of bootcamp-related apps http://www.forbootcamp.org/ MUST-HAVE On OSX when using the external mouse you might want to not use natural scrolling, while keeping it enabled for the trackpad. Scroll Reverser does that! MUST-HAVE This website -might- have more up-to-date AMD GPU drivers for Bootcamp https://www.bootcampdrivers.com/ (but check also the official AMD bootcamp page) Other OSX MUST-HAVE is gSwitch to force integrated GPU only (or discrete only).  Background Music allows to change audio volume per app.  MUST-HAVE Synergy for keyboard/mouse sharing across computers. VirtualBox can be useful and it's free, even if I usually prefer VmWare (sometimes I use the Player with pre-made OS images).  HyperV, included with Windows, can be great too, it's not a bad idea to keep your different work environments in different VMs / drives nowadays, as drive space is not a big deal. On OSX, Parallels is really good. I use Docker for all the times some python library are available on Linux only (e.g. happens for deep neural network stuff...). Command-line / Terminal I love Cathode on OSX. Also on OSX: CoolRetroTerm, which is opensource, but it's not quite as great. MUST-HAVE For OSX, I use Homebrew and Cakebrew. I'm not really a command-line ninja, but I've started adopting it a bit more. I usually install tmux, nnn, tldr, a recent version of nano. Window management various 1Up industries stuff is really good: Fences, Bins (7Stacks is somewhat similar, and free, emulates OSX stacks). SysTools Desktops is a tiny free utility for virtual desktops My own bugfixed version of AnAppADay Jedi Concentrate (a Windows clone of the OSX Think Isolator, Spirited Away is a nice complement to these too, there are clones as well). WindowFX 4 does the same too (and much more) On OSX some people/setups seem to need SmoothMouse to avoid mouse lag There are a lot of other tools that look nifty but I didn't end up using them often... Displayfusion looks neat but I didn't try it yet, the most interesting feature for me is placing a second taskbar with only the applications used on the second monitor there, MultiMon does it for free. A tiling window manager is good if you have a lot of screen space, like WinSplit (OSX alternative: SizeUP) OSX: not a tool, but important, kill the lag in the dock autohide: defaults write com.apple.Dock autohide-delay -float 0 There are tools that provide a GUI on top of the defaults system. E.g. TinkerTool Internet
MUST-HAVE Chrome (w/a session manager to not swear if things crash, a tab auto-suspender, and I also disable flash/other plugins auto-start and use the morphine extension at work) MUST-HAVE DropBox (even if I'm thinking to migrate out of it) Google Calendar Sync, if the company doesn't have decent intranet VPN access MUST-HAVE Skype. MUST-HAVE Zoom is GREAT! For home at least I use a free TeamViewer account (join.me is nifty), which I find many times easier/better than setting up UltraVNC. Splashtop looks promising. Math
I still use the PowerToy Calculator (patched to install on Win7/Vista) MUST-HAVE Mathematica (OSX too) if the studio has a license for it (or I make them buy one!) Python Anaconda distribution that I already mentioned GeoGabra can be useful when tinkering with geometrical constructions, it's quite powerful (currently the beta of v5 supports 3d too, and it's available "portable" as well) but slightly more focused on contraints than I'd like (I'd love something very interactive with optional constrained stuff, like a parametric CAD) Some people swear by TikZ (examples), looks extremely cool but it's not interactive... On the simpler side, and 2d only, DrGeo (portable as well) is great to tinker SciLab which I prefer over Octave (that is though more compatible w/MatLab), but nowadays I don't really care about MatLab-like environments, I prefer either Mathematica or SciPy (Anaconda)