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As he tells it, "I just lay there in the dark going, 'How weird is this? Watch This. But the release of his self-titled solo album was a breakthrough. The couple even had matching tattoos—"Amor Vincit Omnia," Latin for "Love conquers all"—which they covered with new tattoos after their amicable split in Popular Galleries. At one point, he shared a house with "a freebaser," he later told Rolling Stoneand that led to a serious drug problem.

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An embarrassed Urban told Leno that he regretted appearing in the magazine.

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Remember When Keith Urban Posed for Playgirl?

Urban was developing a local reputation as a country artist when he posed for this photo with Smoky Dawson, Australia's original singing cowboy. Up Next: As the baby of the family with one older brotherKeith was called "Suburban. He Had a Cute Nickname. But the first song Keith learned to play in its entirety was the Animals' version of "House of the Rising Sun. Urban had put out one album in Australia and another as frontman for a short-lived band called The Ranch. Follow Purple Clover on Twitter.

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