"I Guess It Never Hurts to Hurt Sometimes" is a song written and originally recorded by Randy VanWarmer on his 1981 album Beat of Love. It was later covered by American country music group The Oak Ridge Boys in 1984, released as the second single from their album Deliver. "I Guess It Never Hurts to Hurt Sometimes" was The Oak Ridge Boys' ninth number one on the country chart. The single went to number one for one week and spent a total of twelve weeks on the country chart.
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