I'll defend Winamp a bit on this front for a few reasons...
1. The download installer is 10MB. A kitchen-sink installation is 50MB. In 2017. The installer for VLC is 30MB, and a kitchen sink install of that is 122MB. iTunes is over 100MB for the installer. Winamp may be bigger than it used to be, but it's still very comfortably on the left of the bell curve - its full installer takes less disk space than the amount of RAM needed by the Pandora website.
2. They've got a custom installer. Don't want the visualizations or CD ripper support or video playback modules? You can opt out of installing them. The 'lite' profile is under 10MB installed. It doesn't play video or support 'modern' skins or have a media library, but if that's a feature rather than a bug, it far eschews iTunes's utter lack of custom install options (oh, you don't have an iPhone and didn't want five services starting with your computer now? sucks to be you!).
3. Truly opt-out of data collection.
4. I don't ever think I've had Winamp crash.
5. Though I hate the Bento skin and its propensity to assume I want the library displayed rather than a small windowshade, every version for the last 20 years has shipped with the 'classic' skin, and short of the added menu options, has looked and worked exactly the same, requiring zero relearning on the part of the user unless they explicitly wished to use a different skin.
So no, the new versions haven't been coded by demoscene savants who could have fit it on a floppy disk with room to spare, but it's still relatively small, functional, stable, and familiar - adjectives that are very infrequent to use when describing most software today.