Don't Let Me Be the Last To Know (2000)

For the fourth single from her album Oops!... I Did It Again, Britney Spears brought in heavy hitters as big and famous as her racktacular titters—country honey Shania Twain co-wrote Don't Let Me Be the Last To Know (2000), and superstar photog Herb Ritts directed the sultry video. Shot in Key Biscayne, the vid features Brit in a bikini and short shorts singing on beaches and in tiki huts, making out with her man in the surf and on the sand, and bending over to bare the Gland Canyon between her barely covered mams. Rumor has it her mama wasn't too pleased with the sexed-up scenes and ample samplings of mammary glands, but what inspires fear in Mrs. Spears will raise high the mighty spear in your pants.