Former skateboarding pro Matt Costa started focusing on the guitar after a skateboarding injury (a shattered leg) in 2003 sidelined him for eighteen months of rehab. He began writing and recording songs and eventually ended up on Jack Johnson's 2005 summer tour. But unlike Jack Johnson, Costa is not an incredibly lame, surfer version of Jimmy Buffett with a carefully-cultivated "Hey, I'm all about chillaxing. Did you notice that I'm wearing sandals on stage? That's because I'm chillaxing" vibe.
Anyway, I'm a sucker for finger picking, and this song ("Astair" from 2005's Songs We Sing) has been stuck in my head all Labor Day. Here is a live version, performed at a Vans store: