| 100% | DEVIL | 5 | "The ___ Wears Prada," film where Meryl Streep plays a demanding boss and editor-in-chief of the fashion magazine Runway |
| 44% | THEDEVILWEARS | 13 | "___ Prada," a 2006 film starring Meryl Streep, where she is the boss of co-star Anne Hathaway: 3 wds. |
| 38% | DEVIL | 5 | "The ___ Wears Prada" (2006 film starring Meryl Streep as a tough boss) |
| 36% | AIR | 3 | "Up in the ___," film where Jason Bateman plays a pragmatic boss who manages a team at an HR consultancy firm |
| 35% | PRADA | 5 | What the Devil wears, in a Meryl Streep film title |
| 35% | PRADA | 5 | It's what the Devil wears, in a Meryl Streep film title |
| 34% | SOPHIESCHOICE | 13 | 1982 film where Kevin Kline and a Holocaust survivor played by Meryl Streep are a couple: 2 wds. |
| 34% | REIDS | 5 | Actress Tara who plays April in "Sharknado" films and Andy, head coach of the Kansas City Chiefs |
| 33% | PRADA | 5 | "The Devil Wears ___," 2006 fashion comedy film starring Meryl Streep and Anne Hathaway |
| 33% | MEN | 3 | "All the President's ___," film where Jason Robards plays a newsroom boss who pushes for nothing but the truth |
| 33% | NINA | 4 | Fashion journalist ___ García who is the editor in chief of "Elle" |
| 33% | SOPHIESCHOICE | 13 | 1982 film starring Meryl Streep, where she plays a Polish immigrant, a role that won her the Oscar for Best Actress: 2 wds. |
| 33% | KEITHRICHARDS | 13 | Rolling Stones guitarist who played a pirate in the third and fourth "Pirates of the Caribbean" films: 2 wds. |
| 32% | OUTOFTIME | 9 | 2003 film in which Denzel Washington plays a police chief suspected of stealing money and killing his lover: 3 wds. |
| 31% | DEVIL | 5 | "The ___ Wears Prada," Meryl Streep film |
| 31% | DEVIL | 5 | "The ___ Wears Prada" (2006 Meryl Streep film) |
| 30% | PRADA | 5 | "The Devil Wears ___" (movie where Meryl Streep played Miranda Priestly) |
| 30% | PRADA | 5 | Devil's fashion choice, in a Meryl Streep film |
| 30% | ERIN | 4 | "___ Brockovich," film where Albert Finney plays a skeptical advocate boss who is also empathetic at the same time |
| 30% | PROPOSAL | 8 | "The ___," film where Sandra Bullock plays a commanding boss who gets engaged to her assistant |
| 30% | BAND | 4 | "The Boys in the ___," 2020 drama film where Jim Parsons reprised his role from a 2018 Broadway show of the same name |
| 30% | DRX | 3 | 1939 film in which Bogart plays a creepy lab assistant, The Return of ___ |
| 30% | WHOOPIGOLDBERG | 14 | "Sister Act" actress who played God in the films "A Little Bit of Heaven" and "It's a Very Merry Muppet Christmas Movie" (2 wds.) |
| 30% | RANGE | 5 | Where the deer and the antelope play, in a song |
| 29% | COPA | 4 | Club in a Barry Manilow song where "music and passion were always the fashion" |
| 29% | OLGA | 4 | Actress Kurylenko who played a Bond girl in the 2008 film "Quantum of Solace" |
| 29% | TED | 3 | Danson who played one of the three men in "Three Men and a Baby" |
| 29% | MERYLSTREEP | 11 | "The Devil Wears Prada" actress who plays a struggling actress on "Only Murders in the Building" (2 wds.) |
| 29% | PRADA | 5 | "The Devil Wears ___," movie starring Meryl Streep who Michael Scott adores and mimics in "The Office" |