“If I Lose” — in full, “If I Lose, I Don’t Care” — is an old-time song that entered the recorded tradition through Charlie Poole and the North Carolina Ramblers, who cut it in 1927. The song is generally credited to Poole and his guitarist Norman Woodlieff, who built it in part from older blues material.
The lyric is a gambler’s swagger — a man laying down his bets and his bravado, declaring that win or lose he does not care. That devil-may-care attitude, common in the gambling and rambling songs of the era, gave it a hard, jaunty appeal.
Like several of Charlie Poole’s recordings, “If I Lose” passed firmly into the bluegrass canon and became a jam-session and stage standard. The version heard here is by Ricky Skaggs and Kentucky Thunder, from their 1997 album “Bluegrass Rules!”
