| 100% | OFFICE | 6 | "___ Space," film where Gary Cole plays a micromanaging boss who is obsessed with TPS reports |
| 35% | ERIN | 4 | "___ Brockovich," film where Albert Finney plays a skeptical advocate boss who is also empathetic at the same time |
| 33% | PROPOSAL | 8 | "The ___," film where Sandra Bullock plays a commanding boss who gets engaged to her assistant |
| 30% | GATSBY | 6 | Title character of classic American literature who is obsessed with a green light |
| 30% | AIR | 3 | "Up in the ___," film where Jason Bateman plays a pragmatic boss who manages a team at an HR consultancy firm |
| 29% | MEN | 3 | "All the President's ___," film where Jason Robards plays a newsroom boss who pushes for nothing but the truth |
| 28% | BLADESOFGLORY | 13 | 2007 film where Will Ferrell played a figure skater: 3 wds. |
| 27% | MELODICALLYSUPERVISED | 21 | Having a boss who will only communicate with you by singing? |
| 27% | JAILHOUSEROCK | 13 | 1957 Elvis Presley film where he plays a prisoner who becomes a star: 2 wds. |
| 27% | THEODDCOUPLE | 12 | 1968 film where Walter Matthau played a slob rooming with a neat freak: 3 wds. |
| 26% | DIPLO | 5 | DJ who had a hit with Where Are Ü Now in 2015 |
| 26% | LUDWIG | 6 | King who was obsessed with castles: Mad King __ |
| 26% | KAA | 3 | Python who is a secondary antagonist with Shere Khan in the Disney animated film "The Jungle Book" |
| 26% | AWRINKLEINTIME | 14 | 2018 fantasy movie in which Reese Witherspoon played a being who flies kids through space: 4 wds. |
| 26% | PSYCHO | 6 | Film where Marion was shown flushing a toilet with its contents visible - a first in the US at the time |
| 25% | PURSUIT | 7 | "The ___ of Happyness," Gabriele Muccino's film where Chris Gardner himself crosses paths with his character played by Will Smith |
| 25% | PEEKABOO | 8 | "Where are you?" game played with a baby |
| 25% | TREEHOUSE | 9 | Play space that might be accessed with a rope ladder |
| 25% | THESECRETLIFE | 13 | With 47-Across, 12/25/13 film about an ordinary guy who fantasizes about being a hero: 3 wds. |
| 25% | TONY | 4 | With 32-Across, undrafted quarterback who played 14 seasons for the Dallas Cowboys and is currently a CBS commentator |
| 25% | AMELIE | 6 | Film where Audrey Tautou plays a quirky Parisienne |
| 25% | REPOMAN | 7 | 1984 film with the tagline "It's 4 a.m., do you know where your car is?" |
| 24% | BORDERTOWN | 10 | A 2006 film starring Jennifer Lopez, in which Martin Sheen - whose birthday it is today - plays her character's boss |
| 24% | NATIVESON | 9 | Best-selling 1940 novel that was adapted into a film, with its author playing the protagonist, in 1951 |
| 24% | MATT | 4 | ___ Cook, "Man with a Plan" actor who plays Sonny in the 2023 film "Champions" |
| 24% | THEDEVILWEARS | 13 | "___ Prada," a 2006 film starring Meryl Streep, where she is the boss of co-star Anne Hathaway: 3 wds. |
| 24% | HENRYCAVILL | 11 | Actor known for playing a DC superhero who will be seen in the new "Mission: Impossible" film: 2 wds. |
| 24% | WAYOFTHEDRAGON | 14 | 1972 action comedy starring Bruce Lee, who was a close friend of Chuck Norris, and is his only released film with him: 4 wds. |
| 24% | EWANMCGREGOR | 12 | Actor who plays the protagonist in "Christopher Robin" which is a fantasy film based on "Winnie-the-Pooh": 2 wds. |
| 23% | ALI | 3 | Whom Will Smith played in a 2001 sports biopic |