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The Riddle" was the first single from American singer/songwriter Five for Fighting's album Two Lights. John Ondrasik has stated that it was the hardest to write of any of his songs, taking 18 months to write. By the end, he had over 100 drafts before he came up with the final version. Although it began as a song on the meaning of life, it later evolved into a song about the love between a father and his son, inspired by his relationship with his own five-year-old son.

"The Riddle" peaked at #40 on the Billboard Hot 100 during an 18-week chart stay. On the Hot Adult Contemporary Tracks chart, the song reached #4.

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