| 100% | HATE | 4 | "10 Things I ___ About You," 1999 rom-com set in a high school starring Julia Stiles and Heath Ledger |
| 59% | HATE | 4 | "10 Things I ___ About You," 1999 romedy starring Heath Ledger and Julia Stiles |
| 45% | ELECTION | 8 | 1999 rom-com set in a high school featuring Reese Witherspoon and Matthew Broderick |
| 45% | HATE | 4 | "10 Things I ___ About You" (rom-com starring Heath Ledger) |
| 41% | ALLTHAT | 7 | "She's ___," 1999 rom-com set in a high school featuring Freddie Prinze Jr. and Rachael Cook: 2 wds. |
| 38% | HATE | 4 | "10 Things I ___ About You" (Heath Ledger starrer) |
| 37% | HATE | 4 | "10 Things I ___ About You" (1999 rom-com) |
| 34% | HATE | 4 | "10 Things I ___ About You" (1999 teen rom-com with an ensemble cast) |
| 34% | ABOUTYOU | 8 | Julia Stiles starred in 10 Things I Hate __ |
| 34% | CLUELESS | 8 | 1995 coming-of-age rom-com set in a high school featuring Paul Rudd and Alicia Silverstone |
| 34% | HEATH | 5 | “10 Things I Hate About You” star Ledger |
| 34% | STILES | 6 | "10 Things I Hate About You" star Julia |
| 33% | HATE | 4 | "10 Things I ___ About You" (Heath Ledger movie) |
| 32% | ROMCOM | 6 | "10 Things I Hate About You" or "How to Lose a Guy in 10 Days" |
| 31% | TEN | 3 | "___ Things I Hate About You" (1999 rom-com) |
| 30% | ABOUTYOU | 8 | 10 Things I Hate __, 1999 Shakespearean rom-com |
| 30% | APBIO | 5 | Sitcom set in a high school |
| 29% | SECRET | 6 | "Our ___ moments in a crowded room / They got no idea about me and you" |
| 28% | TEENWOLF | 8 | 1985 Michael J. Fox film set in a high school (2 wds.) |
| 28% | RUNAWAYBRIDE | 12 | Rom-com starring Julia Roberts and Richard Gere that was one of the Top 10 box office hits of 1999 (2 wds.) |
| 28% | NOTTINGHILL | 11 | 1999 rom com directed by Roger Michell starring Julia Roberts which is also one of the highest grossing rom coms of all times: 2 wds. |
| 27% | IHATE | 5 | "10 Things ___ About You" (1999 rom-com): 2 wds. |
| 27% | STILES | 6 | Julia of '10 Things I Hate About You' |
| 27% | HATE | 4 | "10 Things I ___ About You" (1999 film version of "The Taming of the Shrew") |
| 27% | HATE | 4 | "10 Things I ___ About You" (1999 film based on "The Taming of the Shrew") |
| 25% | APBIO | 5 | Patton Oswalt sitcom set in a high-school science class |
| 25% | AFTERPARTY | 10 | "The ___," series about a high school reunion, starring Tiffany Haddish and Sam Richardson on Apple TV+ |
| 25% | CLUB | 4 | "The Breakfast ___" (John Hughes film set in a high-school library) |
| 25% | APBIO | 5 | Patton Oswalt sitcom set in a high-school science class (3 wds.) |
| 25% | DAZED | 5 | "___ and Confused," 1993 comedy set in a Texan high school featuring Matthew McConaughey and Ben Affleck |