Doesn't even matter if you know his music or not, you will still enjoy his show as long as you aren't expecting dubstep. I saw him at Osheaga in 2010 and I had a fucking blast, and the only song I could think of his was 'I can see clearly now, the rain is gone...'.
In 1999, I saw him open for DMB in Arizona. It was pretty effing sweet. That afternoon, a huge sandstorm blew across the entirety of the Valley of the Sun, blotting out everything. Then it started to rain. After awhile, Jimmy Cliff and band took the stage. As they did so, it proceeded to stop raining and the sun came out from behind the clouds. Jimmy Cliff opened the set with I Can See Clearly Now. Good times in the AZ.
10/29 Hot Chip @ The Fox Theatre
11/07 Rufus Du Sol @ The Mezzanine (?)
11/13 Mr Little Jeans @ The Rickshaw Stop
11/20 Keep Shelly in Athens @ Awaken
I'm at home sick and have been playing Jimmy for the last few hours straight...love this guy's voice and vibe! This would be such a good late afternoon chill set, just relaxing with good friends and good music before nighttime begins (Erykah Badu slot but maybe Outdoor instead). I absolutely love these eclectic video drops, I easily would have overlooked him on the lineup and now he's a must see.