Not wanting to reopen the hip-hop argument, but one artist to check out is K'naan. Meaningful AND good. He's a Somalian refugee, who seems to have found his niche in poetry and hip-hop.
Some songs I've been big on lately:
Eels - I Like Birds
Bedouin Soundclash - When the Night Feels My Song
Neil Young - Unknown Legend
Bob Dylan - Don't Think Twice
George Thorogood - Get a Haircut
The Weakerthans - Our Retired Explorer
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