How can I play music on my speakers while I use my headset for video chat applications like Skype?
Shouldn't this be possible via this PulseAudio sound server that Ubuntu uses?
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Yes this is possible, but you need more than one soundcard (PulseAudio calls these sinks) for this to work. Don't worry, if you have something like a headset that is connected via Bluetooth or USB, then this also counts as another soundcard.
vlc-plugin-pulseis installed. You can then switch between soundcards from within VLC via menu entries Audio > Audio devices.