| 100% | TOPNAME | 7 | Jacob, for baby boys from 1999 to 2012 |
| 39% | JACOB | 5 | Most popular U.S. baby name for boys, 1999-2012 |
| 37% | TONYPARSONS | 11 | Author of novels Men from the Boys and One for My Baby |
| 36% | ALEROS | 6 | Models sold from 1999 to 2004 |
| 36% | IBOOK | 5 | Apple offering from 1999 to 2006 |
| 36% | SONS | 4 | Baby boys, to moms |
| 34% | FEY | 3 | "S.N.L." head writer from 1999 to 2006 |
| 33% | SCI | 3 | ___ Fi (name of a cable channel from 1999 to 2009) |
| 33% | GREED | 5 | Trivia game show hosted by Chuck Woolery from 1999 to 2000 |
| 33% | JON | 3 | Comedian Stewart who hosted "The Daily Show" from 1999 to 2015 |
| 32% | LIAM | 4 | The most common name for baby boys born in America in 2018 |
| 32% | LIAM | 4 | The most common name for baby boys born in America in 2020 |
| 32% | LOUIE | 5 | Stand-up comedian Anderson who hosted "Family Feud" from 1999 to 2002 |
| 32% | NEO | 3 | Role played by Keanu Reeves in three movies from 1999 to 2003 |
| 32% | JON | 3 | Comedian Stewart who hosted the "The Daily Show" from 1999 to 2015 |
| 32% | NOAH | 4 | Second-most-popular name for baby boys in the U.S. in 2022 |
| 31% | TEETHER | 7 | Chewy toy for babies, to help soothe dental pain |
| 31% | PHILJACKSON | 11 | Lakers head coach from 1999 to 2004 and from 2005 to 2011: 2 wds. |
| 31% | SLIDESCALE | 10 | From gentle to steep for some playground equipment? |
| 31% | ALLDAY | 6 | From dawn to dusk, for 24 hours long |
| 31% | LAP | 3 | Place for a baby to sit |
| 31% | CRIB | 4 | Place for a baby to sleep |
| 31% | SAAB | 4 | Swedish automaker from 1945 to 2012 |
| 31% | SAAB | 4 | Swedish carmaker from 1945 to 2012 |
| 31% | ICARLY | 6 | Nickelodeon show from 2007 to 2012 |
| 31% | NEONATES | 8 | Babies from birth to four weeks |
| 30% | WATERBOWL | 9 | Container for dogs to drink from |
| 30% | WHOWANTSTOBEA | 13 | With 19-Across, quiz show hosted by Regis Philbin from 1999 to 2002 (5 wds.) |
| 30% | LICENSED | 8 | __ to Ill, 1986 debut for the Beastie Boys |
| 30% | LULLABY | 7 | Song for rocking a baby to sleep |