2-Winamp (Windows/Mac)

Winamp has been whipping the llama's ass for over 15 years, and that's not a bad thing. it's has come a long way since its early Nullsoft days, back before it was picked up by AOL, and in fact we were just reflecting on how far it's come. Some of the changes were good, some not so much, but overall it's still an amazing jukebox and media player that's relatively lightweight, fast, and customizable. The interface can be as minimal as a shade at the top of your display with tiny playback controls, or as blown out as a full-screen jukebox UI that features search bars, library information in multiple windows organized by artist, album, and song name, a full web browser, and more. It all depends on what you're looking for. Winamp handles all the tasks you'd expect from a media player: It can rip CDs, support crazy file types, sync with mobile devices either via USB, or wirelessly through its well-crafted native Android app. Winamp still has the features you loved about it if you've used it for a long time too: Skins, themes, ShoutCast radio support, visualizations, and more. Many of you praised Winamp for keeping up with the times and adding more streaming music sources to its app, while others noted that its Android app and its beta Mac client show that the developers behind it show no signs of slowing down on it. Winamp is definitely more bloated than it used to be (adding things like AOL music, video support, etc) back in the old days, but it's still flexible, functional, and completely free. There are a few extra features available in the $20 Winamp Pro version, but the free version is probably enough for most people. Winamp has been straightforward, easy-to-use, and a solid app for years—almost a constant compared to other apps that have come and gone since.