40 Saddest Country Songs of All Time

Cry, Cry, Cry: From George Jones to Brad Paisley, the biggest weepers ever

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5. John Michael Montgomery, "The Little Girl"

A dysfunctional family's plight hits a disastrous final note in John Michael Montgomery's soap opera tale "The Little Girl." The last Billboard Hot Country Songs Number One of his career details a young girl hiding behind the couch while her drug-addled ma and alcoholic pa duke it out — with fatal results. Backed by harmonies from bluegrass stars Alison Krauss and Dan Tyminski and an arrangement to urge on the waterworks, Montgomery remains even-keeled as the fable reaches its spiritual conclusion.

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