| THEAPARTMENT | 1960 comedy starring Shirley MacLaine as an elevator operator pursued by two men: 2 wds. |
| GUARDINGTESS | 1994 comedy starring Shirley MacLaine as a former First Lady at odds with her Secret Service agent: 2 wds. |
| AMEN | "Two men, two worlds, one cause" ran the tagline to this 2002 Costa-gavras release (4) |
| PUSHTHEBUTTONS | Take charge, like an elevator operator? |
| SWEETCHARITY | 1969 musical starring Shirley MacLaine as a luckless dancer looking for love: 2 wds. |
| EVENINGSTAR | "The ... ...", Robert Harling film starring Shirley MacLaine as Aurora Greenway (7,4) |
| PINUP | Model, say, initially pursued by two characters abroad |
| CHASED | Pursued by two boys |
| SUNDAY | 1960 comedy-drama film starring Melina Mercouri co-starring, written and directed by Jules Dassin (5,2,6) |
| NEVERON | 1960 comedy-drama film starring Melina Mercouri co-starring, written and directed by Jules Dassin (5,2,6) |
| APARTMENT | The -, 1960 comedy-drama film starring Jack Lemmon and Shirley MacLaine (9) |
| SEANPENN | Two time Academy Award winning actor of Mystic River who appeared in a guest role on Two and a Half Men: 2 wds. |
| PLEASEDONTEATTHEDAISIES | 1960 comedy film starring Doris Day and David Niven, partly inspired by a book of the same name by Jean Kerr |
| NORTH | 1960 comedy-Western film starring John Wayne and Stewart Granger (5,2,6) |
| ONEOVERTHEEIGHT | 1960 comedy revue performed at the Duke of York's Theatre written by Peter Cook and starring Kenneth Williams |
| ANDA | Two ___ Half Men (2 wds.) |
| CHARLIESHEEN | Onetime star of Two and a Half Men (2 wds.) |
| ADEXECS | "Mad Men" men (2 wds.) |
| STANLEE | Cocreator of the Fantastic Four and the X-Men: 2 wds. |
| JANUARYJONES | Actress of the month who played Betty Francis on "Mad Men": 2 wds. |
