| 100% | LOW | 3 | ___-rise jeans, below-the-belt denim fashion of the 2000s, rocked by Britney Spears in "I'm A Slave 4 U" |
| 42% | MINI | 4 | ___ skirt, short fashion of the 2000s, rocked by Britney Spears in "...Baby One More Time" |
| 37% | CULOTTE | 7 | Fashion-forward split skirt of the 2000s, rocked by Sarah Jessica Parker in "Sex and the City" |
| 32% | TRUCKER | 7 | ___ hat, "gimme" headgear of the 2000s, rocked by Ashton Kutcher in "Punk'd" |
| 30% | HAIR | 4 | ___ bow, bedazzled fashion accessory of the 2000s, often sported by the "Mean Girls" in the popular 2004 film |
| 27% | FRIDAY | 6 | When "I'm in love," in a 1992 hit by the Cure |
| 27% | SPUR | 4 | "Ola! I'm ___ cola, a dupe of cola! I was launched in 1948 and I'm synonymous with the San Antonio NBA team" |
| 27% | DIET | 4 | "Ola! I'm ___ Rite, a dupe of cola! I was introduced in the late 1950s and was one of the first colas with zero calories!" |
| 27% | ECLIPSE | 7 | "Total ___ of the Heart," hit song by Bonnie Tyler with a celestial phenomenon in its title |
| 26% | JUPITER | 7 | "Drops of ___ (Tell Me)," 2001 song by Train with the Solar System's largest planet in its title |
| 26% | WILL | 4 | "___ You Love Me Tomorrow," question posed by the Shirelles in a 1961 single |
| 26% | HEY | 3 | "___, Soul Sister," 2009 song by rock band Train, and maybe the start of a conversation |
| 26% | FINN | 4 | Dewey ___, iconic teacher played by Jack Black in the 2003 film "School of Rock" |
| 25% | NEED | 4 | "I ___ to Know" (song by a rock artist who left us in 2017) |
| 25% | ATBATS | 6 | The 4 of a 2-for-4 line in baseball, say |
| 25% | TONIGHT | 7 | "___ (I'm Loving You)," 2010 song by Enrique Iglesias featuring rapper Ludacris that peaked at No. 4 on the US Billboard Hot 100 |
| 25% | TAB | 3 | "Ola! I'm a dupe of cola! I hit the market in 1963 and I'm synonymous with a can opener" |
| 24% | KNEED | 5 | Hit below the belt, in a way |
| 24% | ONE | 3 | Number of ribs ordered by an annoying customer played by Chris Rock in "I'm Gonna Git You Sucka" |
| 24% | AGIRL | 5 | "I'm also just ___, standing in front of a boy, asking him to love her" (classic rom-com line) |
| 24% | BONO | 4 | Lead singer of "U2," rock band that was popular in the 1990s and the 2000s |
| 24% | WOMAN | 5 | "The __ in Me": Britney Spears memoir |
| 24% | LARA | 4 | ___ Jean Covey, protagonist of Jenny Han's "To All the Boys I've Loved Before" |
| 24% | BELIEVE | 7 | "Do You ___ in Magic," question posed by the Lovin' Spoonful in a 1965 song |
| 23% | LARRY | 5 | "The ___ Sanders Show," sitcom about the happenings in the office of a late-night talk show starring Garry Shandling |
| 23% | IMA | 3 | "___ Slave 4 U" (Britney Spears song) |
| 23% | SPY | 3 | ___ balloon (type of flying object shot down by the U.S. in February, 2023) |
| 23% | PIBB | 4 | "Ola! I'm Mr.___, a dupe of cola! I was introduced in 1974 and I'm a spicy cherry flavor" |
| 23% | BREAK | 5 | "___ the Ice," 2007 hit song by Britney Spears |
| 23% | LINCOLN | 7 | Abraham ___, 16th President of the U.S.A. and the first to sport a beard in office |