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1.
1. One of the many boys from the film Song For A Raggy Boy
2. A person of any gender, usually from the ages of ten to fifteen who often gets into fights and loses them, but is smart, rebellious, and doesn't give a damn. Most of them like literature, history, or poetry.
The raggy boy may have lost her fight, but he was still cocky as ever.
by Katya R. March 08, 2009
 
2.
Any kid or teen who is shy, meek, afraid, or tough, but is at the same time secretly smart and cool, or in any way like the boys from Song For A Raggy Boy

Also any cool, kick ass Irish reform school kid.
The raggy boy was pale and scared-looking, but was really plotting to scam his parents.
by TimeOfYourLife August 21, 2008