I think it's up to the whim of the FA whether or not they turn the system on...most of my flights are music-free...but sometimes a FA in a good mood will turn on the music during boarding, and after landing too.
As a kid flying Air Canada's 747s, DC8s and L1011s to MIA, I remember they always had boarding music - usually Dionne Warwick's "Do you know the way to san jose" and "Say a little prayer". In hindsight, neither title was very appropriate for flying
I tried very hard to get my hands on either a copy of the Hawai'i boarding music, or a playlist of the tunes so I could track them down myself. CO steered me to the production company they use for the inflight entertainment, who then steered me to another company that did the Hawai'i videos - but they would not give me a copy of the audio portion or tell me which music was on the playlist
If anyone else knows something about the music selections for that video (hint hint to CO insiders), I would love to get a list of the selections.