FooBar 2000 – this product is perfect for playing music without all the extra crap from iTunes.
VLC Media Player – simply the best multi-format video media player. VLC can also rip DVDs to MP4.
Handbrake – this product is great for adjusting the quality of videos. You can make MP4s smaller for iPhones or iPads.
MakeMKV – this product helps convert DVDs you own so you can play them on your devices without DVD players.
Open Source Utility Software
WinSCP – this secure file program is great for moving files between servers.
PuTTY – use this to access secure servers through the command line.
WinRAR – use this software to zip and archive folders and files.