| ITALIANJOB | The _ _: 1969 film starring Michael Caine and Noel Coward, and featuring three Mini Coopers (7 ,3) |
| THEITALIANJOB | 1969 film starring Michael Caine as Charlie Croker (3,7,3) |
| ITALIAN | 1969 film starring Michael Caine, 'The - Job' (7) |
| ONIONSONG | The __ ___, 1969 chart hit for Marvin Gaye and Tammi Terrell |
| SPIRIT | Blithe ___, play by Noel Coward and 2020 film (6) |
| SIRS | Noel Coward and others |
| NEWME | "A Brand ___ ___" (1969 Dusty Springfield song, two words) |
| HELLODOLLY | 1969 film starring Barbra Streisand (5,5) |
| ANDTHE | 1969 film starring Paul Newman and Robert Redford in the title roles (5,7,3,3,8,3) |
| SUNDANCEKID | 1969 film starring Paul Newman and Robert Redford in the title roles (5,7,3,3,8,3) |
| BUTCH | 1969 film starring Paul Newman and Robert Redford in the title roles (5,7,3,3,8,3) |
| CASSIDY | 1969 film starring Paul Newman and Robert Redford in the title roles (5,7,3,3,8,3) |
| ARRANGEMENT | The ___, 1969 film starring Kirk Douglas and Faye Dunaway |
| COWBOY | Midnight ___ 1969 film starring Dustin Hoffman that won the Academy Award for Best Picture |
| SECRETSERVICE | On Her Majesty's ___, 1969 film starring George Lazenby as James Bond (6,7) |
| CAMPING | Carry on ___, 1969 film starring Sidney James (7) |
| GRIT | True ___ 1969 film starring John Wayne |
| OCEANSELEVEN | 2001 heist film featuring three People's Sexiest Man Alive winners (George Clooney Brad Pitt and Matt Damon): 2 wds. |
| THESUMMERWINE | Last of ____ , TV sitcom first shown in 1973 featuring three old men and their misadventures (3,6,4) |
| OBLONGBOX | 'The ---', 1969 film starring Vincent Price and Christopher Lee (6,3) |
