My choices would be:
"Gambler" (not even Madonna herself remembers it. LOL)
"You'll See" (you never hear of this masterpiece. Possibly her finest ballad personally)
"Nothing Really Matters" (haven't a clue why this charted so BAD)
"American Life" (was judged too quick based on the video in my opinion)
That's as far as I'm thinking right now, but know there's more. LOL.