I just installed Winamp 2.95. That did the trick.
I disliked anything post-Winamp 2.x.
That compact mode is one of the things I always liked most about the program. I guess I don't listen to music on my computer much anymore (aside from right now, coincidentally). I have Foobar installed, but I hate the UI and it has one especially obnoxious behavior: I have all my folders on the left side. When it's expanded the songs are in the correct order, but when I add the songs to the current playlist, apparently all of a sudden it gets confused by the track numbers and does the old 1, 10, 11, 2, 3 thing. It's really annoying.
Anyway, long story short I've simplified my computing life and I merely use VLC to play any and all media. It has no media management (just playlists), but I don't want that (I like my folders). At it's most compact it's about 10 times the size of the most compact Winamp, but I've got 30" of screen to work with

*edit*
ps- I love to code HTML while listening to Dragonforce at full volume. Damn I'm so happy to not be working at a law firm anymore. Those tools can suck it.