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Britney Spears - Autumn Goodbye (over 1000)
Britney Spears - Stronger (over 1000)
Britney Spears - Circus (over 400
Britney Spears - Lucky (over 1000)
Britney Spears - Baby One More Time (over 800)

My top 5, I say 'over' because I don't how many times exactly, just at least as many times as I have listed. The total times I've listened to Britney's music would be very large as I have listened to at least 4 tracks a day everyday on my MP3 Player (and since 2009 DSi) since 2004. And on average 8 tracks a day, usually with repeated listening, (including CD's, internets, radio etc) since 2001.