Apple - How to display the VLC playlist and the main window simultaneously
It is rather simple. The question is old but since I was just checking myself for the same problem and others might to.
Hit ⌘ + , to open VLC preferences. Uncheck the Play video in main window option. In the interface tab the one that usually opens first.
Videos will spawn in a seperate window and the main holds the playlist.
Under the Menu item "View" see "View>Docked Playlist". If it has a CHECK next to it, it is "Docked", all in 1 window. If you remove the CHECK, you will see the "Video" and "Playlist", in 2 windows.
(I thought the original answer was saying "View", as in "look at" or "look for" the option "unCheck" ... and spent forever unsuccessfully going through the Preferences looking for "unCheck", when, obviously, "VIEW" was a MENU ITEM, at the top of the VLC window!)