I usually have some oldschool on when I chill, changes everyday though. I'd recommend any of the Marley's, my favorite being Stephen Marley. If you like distant relatives you'll like
De La Soul Is Dead is a great, great, great album to have on while chilling.
This is juts my fav song on the album for said purposes
www.youtube.com/watch?v=C8OaRYAZJp4This is a classic too, something I throw on every once in a while. Sublime's
Robbin the Hoodwww.youtube.com/watch?v=HGx373PA3_0And goddammit if the Gorillaz didn't make some of the best chilling music known to man
www.youtube.com/watch?v=bAiUWPZkcCs