A "level up" moment in my life was freshman year when a roommate pointed me to DI.fm to explore electronic music streams. The default client to load the stream at the best bitrate was Winamp, which opened me to an entire world of 1. the music I was looking for before Pandora/Spotify/etc existed, and 2. skinnable, user-friendly software.
Those were good times.
1. https://github.com/captbaritone/webamp