| 100% | PIE | 3 | "American ___" (1999 Jason Biggs comedy) |
| 87% | AMERICANPIE | 11 | DESSERT: 1999 Jason Biggs teen comedy: 2 wds. |
| 86% | AMERICANPIE | 11 | Raunchy 1999 Jason Biggs comedy set at East Great Falls High: 2 wds. |
| 75% | BIGGS | 5 | Jason —, actor who played Jim Levenstein in 1999 film comedy American Pie |
| 74% | PIE | 3 | "American ___" (1999 comedy starring Jason Biggs) |
| 72% | PIE | 3 | "American ___" (1999 teen comedy starring Jason Biggs) |
| 71% | AMERICANPIE | 11 | 1999 film comedy starring Jason Biggs as Jim Levenstein |
| 64% | ELSE | 4 | "Anything ___" (2003 Jason Biggs romantic comedy) |
| 50% | DROP | 4 | "___ Dead Gorgeous," 1999 American comedy film directed by Michael Patrick Jann, starring Allison Janney |
| 46% | PIE | 3 | "American ___" (1999 comedy) |
| 46% | TED | 3 | American comedy |
| 45% | PIE | 3 | "American ___" (1999 movie comedy) |
| 45% | PIE | 3 | "American ___" (1999 film comedy) |
| 45% | PIE | 3 | "American ___" (1999 comedy film) |
| 45% | AMERICANPIE | 11 | 1999 hit comedy |
| 44% | GLEE | 4 | American musical comedy drama |
| 44% | MONTANA | 7 | American musical comedy: Hannah ___ |
| 42% | MONA | 4 | American crime comedy film "Drowning ___" |
| 41% | REPO | 4 | American sci-fi comedy film "___ Man" |
| 41% | GALAXYQUEST | 11 | 1999 comedy featuring aliens called Thermians |
| 41% | ELECTION | 8 | 1999 dark comedy starring Reese Witherspoon |
| 41% | BOWFINGER | 9 | 1999 Steve Martin/Eddie Murphy comedy |
| 41% | UGLY | 4 | "___ Betty," American comedy series |
| 41% | EDTV | 4 | 1999 Ron Howard comedy |
| 41% | RUNAWAYBRIDE | 12 | 1999 Garry Marshall comedy |
| 40% | DOGMA | 5 | 1999 comedy where Alanis Morissette played God |
| 40% | GIAMBI | 6 | 2000 American League MVP Jason |
| 40% | BRAZIL | 6 | Futuristic comedy; South American country |
| 40% | MYSTERYALASKA | 13 | 1999 Russell Crowe comedy-drama |