| 100% | SHESALLTHAT | 11 | 1999 rom-com with Freddie Prinze Jr. and Rachael Leigh Cook |
| 64% | SHES | 4 | "___ All That," a 1999 romantic comedy starring Freddie Prinze Jr. and Rachael Leigh Cook |
| 63% | ALL | 3 | "She's ___ That," a 1999 romantic comedy starring Freddie Prinze Jr. and Rachael Leigh Cook |
| 63% | THAT | 4 | "She's All ___," a 1999 romantic comedy starring Freddie Prinze Jr. and Rachael Leigh Cook |
| 56% | ALLTHAT | 7 | "She's ___," 1999 rom-com set in a high school featuring Freddie Prinze Jr. and Rachael Cook: 2 wds. |
| 42% | NOTTINGHILL | 11 | 1999 rom-com with Julia Roberts and Hugh Grant |
| 38% | SCOOBYDOO | 9 | 2002 film comedy starring Freddie Prinze Jr and Sarah Michelle Gellar |
| 36% | NOTTING | 7 | __ Hill, rom com with Julia Roberts and Hugh Grant |
| 34% | SHES | 4 | "___ All That," rom-com starring Freddie Prinze Jr. |
| 30% | MUSTLOVE | 8 | __ Dogs, rom-com with Diane Lane and John Cusack |
| 30% | ELECTION | 8 | 1999 rom-com set in a high school featuring Reese Witherspoon and Matthew Broderick |
| 29% | YOURE | 5 | "___ Cordially Invited" (2025 rom-com with Will Ferrell and Reese Witherspoon) |
| 27% | FLAMBEING | 9 | Cooking with alcohol and fire |
| 26% | HATE | 4 | "10 Things I ___ About You," 1999 rom-com set in a high school starring Julia Stiles and Heath Ledger |
| 26% | LOVEAGAIN | 9 | Rom-com starring 38-Across and Priyanka Chopra Jonas with the tagline "Destiny has a plan" (2 wds.) |
| 26% | MATRIX | 6 | 1999 movie with Neo and Morpheus, The __ |
| 25% | JUSTGO | 6 | "___ with It," 2011 rom-com starring Adam Sandler and Jennifer Aniston: 2 wds. |
| 25% | SHESALLTHAT | 11 | 1999 rom-com based on “Pygmalion” |
| 25% | HOMEEC | 6 | Class with cooking and sewing, informally |
| 25% | INSTINCT | 8 | 1999 drama starring Anthony Hopkins and Cuba Gooding Jr |
| 25% | DRIVEMECRAZY | 12 | 1999 rom-com starring Melissa Joan Hart |
| 24% | INSTINCT | 8 | 1999 film drama starring Anthony Hopkins and Cuba Gooding Jr |
| 24% | DOO | 3 | "Scooby-___," 2002 live-action film starring Freddie Prinze Jr. that is based on the popular mystery cartoon |
| 24% | SHES | 4 | "___ All That" (Freddie Prinze Jr. film) |
| 24% | JAMBALAYA | 9 | Cajun rice dish cooked with sausage and shrimp |
| 24% | RUNAWAYBRIDE | 12 | Rom-com starring Julia Roberts and Richard Gere that was one of the Top 10 box office hits of 1999 (2 wds.) |
| 24% | RATPACK | 7 | Sinatra, Martin, Davis Jr., Lawford, and Bishop, with "The" |
| 24% | FOODIES | 7 | People with a strong interest in cooking and dining |
| 23% | LOVE | 4 | With 35-Across, 2021 Netflix rom-com starring Jimmy O. Yang and Nina Dobrev |
| 23% | CHEW | 4 | Cooking-themed talk show starring Carla Hall and Michael Symon, with "The" |