If you've ever been on the L platform in the Union Square Subway Station around 10 PM and seen a young guy playing guitar surrounded by swooning teenage girls, you've probably just met Theo Eastwind. Rapidly becoming a Greenwich Village staple, Theo's an intelligent songwriter to be sure, infusing clever lyrics with a very personal simplicity and a frequently haunting guitar part. He tends to underplay the background parts, letting his lyrics and melodies speak for themselves - the way it should be, in my opinion. He sells his CDs for $10 a pop when he plays, and I think it's a solid investment.
Checking his website ('cuz even subway performers have websites nowadays) http://www.theoeastwind.com, I discover he's got quite a discography under his belt - three albums of original material. I also discover he's started his own production company, TheoSophical Music, that he's sold 28,000 copies of his albums and that he's played at The Mercury Lounge, The Bottom Line and CB's Gallery. Even with all that accomplished, he's still down in the subways three nights a week, probably because it's a hell of a time. More power to you, Theo.
His bio (which is quite a story in and of itself, involving a twisted childhood, a classic 'coming to america' story and a love of pastry) is available here: http://www.theoeastwind.com/bio.htm