That's a lonely place
My mama said "Son, why such a lonely face?"

from Jay Electronica – Dear Moleskine Lyrics on Rap Genius

Meaning

Jay plays on the typical question of “why the long face?” He replaces the “long” with “lonely” to give the character’s depression an even more exaggerated feeling

He’s not just sad, but he feels alone in his situation — no one, not even his mother, can relate to him

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