| Madonna or Britney Spears | 25 |
| Madonna or Cher, e.g. | 21 |
| Madonna played her | 18 |
| Madonna portrayal | 17 |
| Madonna rendition | 17 |
| Madonna role | 12 |
| Madonna role, 1996: 2 wds. | 26 |
| Madonna song | 12 |
| Madonna song of 2000 | 20 |
| Madonna title role | 18 |
| Madonna was on its first cover in May 1985 | 42 |
| Madonna was one as a tween | 26 |
| Madonna wore a pointy one | 25 |
| Madonna's "A League of Their Own" role | 52 |
| Madonna's "La --- Bonita" | 39 |
| Madonna's "La Isla ___" | 37 |
| Madonna's "La __ Bonita" | 38 |
| Madonna's "La ___ Bonita" | 39 |
| Madonna's "Material __" | 37 |
| Madonna's "Truth or _____" | 40 |
| Madonna's "___ Don't Preach" | 46 |
| Madonna's "___ the Groove" | 40 |
| Madonna's adopted Kabbalah name | 35 |
| Madonna's announcement after her workout with the 3-time American League MVP? | 81 |
| Madonna's co-star in ''Evita'' | 50 |
| Madonna's ex | 16 |
| Madonna's ex Sean | 21 |
| Madonna's first top 10 song | 31 |
| Madonna's motto? | 20 |
| Madonna's music | 19 |
| Madonna's role in "A League of Their Own" | 55 |
| Madonna, according to the stars | 31 |
| Madonna, e.g. | 13 |
| Madonna, for one | 16 |
| Madonna, originally | 19 |
| Madonna, to the Brits | 21 |
| Madonna, with "the" | 29 |
| Madonna-and-child artwork | 25 |
| Madonna-and-child sculpture | 27 |
| Madragues | 9 |
| Madras clothing | 15 |
| Madras dress | 12 |
| Madras dress that's taken up by hitches? | 44 |
| Madras dresses | 14 |
| Madras garb | 11 |
| Madras garment | 14 |
| Madras garments | 15 |
| Madras is here | 14 |
| Madras mammy | 12 |
| Madras masseur | 14 |
| Madras master | 13 |
| Madras masters | 14 |
| Madras melodies | 15 |
| Madras mister | 13 |
| Madras monarch | 14 |
| Madras money | 12 |
| Madras moola | 12 |
| Madras motif | 12 |
| Madras Mr. | 10 |
| Madras music | 12 |
| Madras music with multiple motifs | 33 |
| Madras nurse | 12 |
| Madras title | 12 |
| Madras town | 11 |
| Madras V.I.P. | 13 |
| Madras wear | 11 |
| Madras wraps | 12 |
| Madras, e.g. | 12 |
| Madre and Leone | 15 |
| Madre or Mist lead-in | 21 |
| Madre or Nevada | 15 |
| Madre's baby | 16 |
| Madre's boy | 15 |
| Madre's brother | 19 |
| Madre's brothers | 20 |
| Madre's delivery | 20 |
| Madre's emphatic order to a niño | 39 |
| Madre's hermana | 19 |
| Madre's hermano | 19 |
| Madre's hermanos | 20 |
| Madre's kin | 15 |
| Madre's little boy | 22 |
| Madre's little one | 22 |
| Madre's milk | 16 |
| Madre's sister | 18 |
| Madre's sisters | 19 |
| Madre's treasure | 20 |
| Madres' kin | 15 |
| Madrid addressee, for short | 27 |
| Madrid afternoon | 16 |
| Madrid airport item | 19 |
| Madrid arena figure | 19 |
| Madrid art center | 17 |
| Madrid art gallery | 18 |
| Madrid art museum | 17 |
| Madrid attraction | 17 |
| Madrid bed | 10 |
| Madrid calendar start | 21 |
| Madrid coin | 11 |
| Madrid daily | 12 |