I loved using Winamp over say Windows Media Player in the early days of MP3s.
You could throw hundreds or thousands of tracks into your playlist and could scroll incredibly quickly through them, even on relatively slow PCs of the day. In an age before Spotify where to have vast collections was appealing, all my friends could scan each others' playlists and immediately start playing a song.
The speed of the software really did help discover new music. Scroll, double-click, scroll, double-click, scroll, double-click.