#1
It's 4 in the morning over here in California and I can't sleep at all. To kill some time until morning, I decided to take a couple of classic Christmas tunes and arrange them together into a Christmas medley of sorts. So far, I have : Deck the Halls, We Wish You a Merry Christmas, Silent Night and Winter Wonderland. I'm not really sure how I should arrange this though. I was thinking of arranging it as a traditional song structure with a chorus and bridge but I"m not sure if it would work musically. I'm looking at the tabs right now and the songs seem to use a lot of the same notes but I'm still not sure. Can anyone offer some advice on how I should arrange this?
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#2
Arrange it for a jazz band. It'll be fun.

Get a lead instrument (trumpet, trombone, sax, whatever) to play the main melody. Syncopate it a bit.

Arrange the sax's (or a few trumpets+trombones) playing chords. Make sure you use as many notes from Bb and Eb as possible (even if it means transposing the song) and try to use as much counterpoint as possible.
Also try to add extensions to these chords. Major chords functioning as an I or IV chord can become maj6 or maj7 or maj9 chords, major chords functioning as a V chord can become a 7th or a 9th or even an altered dominant. You could also try to do some tritone subs or passing chords.

Make a bass guitar walk, preferably to the chords. Make sure it sounds right with the main melody (probably requires counterpoint).

Get the section that you didn't use for the chords (so if you used sax's, use the brass section here) to play countermelodies (once again, use counterpoint) or fills.

You might want to get a guitar and a piano to play the chords too, but alot of jazz bands don't have pianists and guitarists. It's really not essential.

Just a few ideas of mine. I'm currently about half-way through a jazz arranging book.
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#3
^ Nothing sounds better than Christmas Jazz music and those are some great tips. Since he pretty much covered everything, I can suggest using a classical guitar that is finger picked. Try and get most of the melody into chords rather than single notes. You can mix and match but for the majority of the holiday jazz tunes out there, chordal melodies sound great. Also, when you're arranging the drums I only have one word for you: Brushes!
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