Although demonstrating more calypso than reggae, one of the most successful recent marriages of Afro-Caribbean music and jazz hails from the birthplace of calypso, Trinidad. I posted some of this very nice young trumpet player previously. I love the relaxed feeling in this style; even in the more swingy tunes.
https://m.youtube.com/watch?v=Ad3uG7-2tVs
https://m.youtube.com/watch?v=YmhajnlB9Og
https://m.youtube.com/watch?v=rsayHOVvS8s
https://m.youtube.com/watch?v=e6rfAnQ9DDA
https://m.youtube.com/watch?v=Ad3uG7-2tVs
https://m.youtube.com/watch?v=YmhajnlB9Og
https://m.youtube.com/watch?v=rsayHOVvS8s
https://m.youtube.com/watch?v=e6rfAnQ9DDA