Coming off her 1994 album Bedtime Stories, the video for "Secret" was a jazzy, slinky, cleavage-ridden affair. Check out her hip nose ring, possibly a vestige from her dalliance with Tupac Shakur around this period.
Madonna keeps it pretty demure here, but it's the dudes in the clip that make this a naughty pick. Sort of the opposite of George Michael's "Freedom '90". All the rain, sweat, and fighting...
This one is pretty simple, making good use of Madonna's lip area, lingerie, and a bedroom. As YouTube commenter Ego1c proclaimed "MY DIVA MY QUEEN MY LIFE I LOVE YOU BITCH". Ditto, or something.
By 2003, Madonna wasn't exactly washed-up, but she wasn't on the tips of everyone's tongue. She was relatively quiet, save for that atrocious "American Pie" cover, until this clip with pretender-to-her-throne, Britney Spears, and that kiss seen 'round the world at the MTV Video Music Awards that year.
Just a few years later, Madonna snagged Justin Timberlake for this video, which had us all rooting for the pair to put some p's in v's in the back of that car. Because you know that would have irked Brit-Brit something awful.