| SURPRISE | Shanghai --------, adventure comedy film starring Sean Penn and Madonna (8) |
| GOONIES | The ___ 1985 adventure comedy film starring Sean Astin and Josh Brolin |
| SWEETAND | And 16 1999 comedy-drama film starring Sean Penn, Samantha Morton and Anthony LaPaglia (5,3,7) |
| MYSTICRIVER | 2003 crime drama film starring Sean Penn and Tim Robbins (6,5) |
| IAMSAM | 2001 film starring Sean Penn and Michelle Pfeiffer (1,2,3) |
| GANGSTER | 2013 crime drama starring Sean Penn, Josh Brolin and Ryan Gosling (8,5) |
| EVIDENCE | Body of ___, racy 1993 thriller film starring Willem Dafoe and Madonna (8) |
| UTURN | 1997 film thriller starring Sean Penn and Jennifer Lopez |
| ATCLOSERANGE | 1986 film drama starring Sean Penn and Christopher Walken (2,5,5) |
| SHANGHAI | Bad 1986 flick w/ Sean & Madonna Penn, ________ Surprise. |
| REDLINE | World War II drama starring Sean Penn and John Travolta, The Thin... (3,4) |
| MILK | Oscar-winning drama starring Sean Penn and Emile Hirsch (4) |
| LAKECOMO | Lombardy holiday area, favoured by George Clooney and Madonna (4,4) |
| GAYICONS | Mariah Carey and Madonna, for two |
| EVAPERON | Historical figure who has been played by Patti LuPone and Madonna |
| SWEETANDLOWDOWN | 1999 Woody Allen comedy-drama film starring Sean Penn, Samantha Morton and Anthony LaPaglia |
| POPDIVAS | Cher and Madonna, e.g. |
| POPICONS | Ariana and Madonna |
| TAKEABOW | Title shared by #1 hits from Rihanna in 2008 & Madonna in 1995: 3 wds. |
| LOWDOWN | 1999 Woody Allen comedy-drama film starring Sean Penn, Samantha Morton and Anthony LaPaglia (5,3,7) |
