If you want the "Greatest Hits" experience, these three collections are the definitive summaries of this period:
Her most political work, featuring folk-hop textures. Key tracks: "Hollywood" , "American Life" . Madonna - Discography [1982-2010]
A smoother, R&B-influenced pivot. Key tracks: "Secret" , "Take a Bow" , "Human Nature" . If you want the "Greatest Hits" experience, these