| DARE | "Truth or ___" (documentary also called "In Bed With Madonna") |
| NEO | What "Mr. Anderson" was also called in "The Matrix" |
| EVITA | Lloyd Webber musical filmed with Madonna in 1996 (5) |
| PEROXIDE | And 24 Old boxer in deep trouble with Madonna. (8,6) |
| BLONDE | Old boxer in deep trouble with Madonna. (8,6) |
| ARQUETTE | Rosanna, U.S. actress who starred with Madonna in the 1985 comedy film Desperately Seeking Susan (8) |
| MYERS | Mike who made out with Madonna for an "SNL" skit |
| TIRED | Drunk tried to lie with Madonna - gross (5,3,9) |
| PUTATIVE | Supposed place with Madonna film to be to the west (8) |
| SHEP | Pettibone who co-wrote "Vogue" with Madonna |
| DIE | James Bond movie with Madonna theme tune, ... Another Day |
| GAULTIER | French designer who has collaborated with Madonna, Jean-Paul _ (8) |
| AMANDAHOLDEN | She's seen doing Italian Job - ace with Madonna held off (6,6) |
| THEIR | "A League of ___ Own" (1992 film with Madonna) (5) |
| ORBIT | Record producer who worked with Madonna, William ----- (5) |
| MASONRY | Stonework with Madonna bearing child (7) |
| PRIMADONNA | Temperamental diva halves prizes with Madonna (5,5) |
| MADEINAMERICA | O.J.:___ documentary series based on the life of O. J. Simpson that won the Oscar for Best Documentary Feature in 2016: 3 wds. |
| APU | "The Problem with ___" (documentary by Hari Kondabolu) |
| CASTLE | Brooklyn ___ documentary film following five chess players in a Brooklyn school |
