| 100% | JEEVES | 6 | Ask ___, answer engine popular in the '90s and 2000s now called Ask.com |
| 47% | ACAI | 4 | Antioxidant-rich purple berry that became popular in the 2000s and is now common in breakfast bowls |
| 45% | HOTMAIL | 7 | Email service popular in the '90s and 2000s acquired by Microsoft and rebranded as Outlook |
| 45% | NETSCAPE | 8 | Computer services company with "Navigator" and "Communicator" web browsers that were popular in the '90s and 2000s |
| 40% | MATCHA | 6 | ___ tea latte, green drink that became popular in the 2010s and is now a Starbucks offering |
| 40% | AVOCADO | 7 | ___ toast (guacamole fruit), open sandwich that became popular in the 2010s and is now a breakfast staple |
| 37% | MYSPACE | 7 | Social networking service created by Tom Anderson and Chris DeWolfe that was popular in the 2000s |
| 36% | POGS | 4 | Game of milk caps that was popular among kids in the 90s and is one of the best-selling Christmas gifts |
| 36% | DAILYJUMBLE | 11 | Popular newspaper puzzle, and a hint to what's hidden in the answers to starred clues |
| 35% | OURGANG | 7 | Shorts popular in the 1920s and '30s |
| 35% | NAMATH | 6 | Jet popular in the 1960s and '70s |
| 35% | SCRUNCHIES | 10 | Bands popular in the eighties and nineties |
| 34% | DUVALL | 6 | Robert, actor in The Godfather and Apocalypse Now |
| 34% | DECO | 4 | Art ___ (style popular in the 1920s and 1930s) |
| 34% | ARTDECO | 7 | Architectural style popular in the 1920s and 1930s |
| 34% | SWING | 5 | Jazz style popular in the 1930s and 1940s |
| 34% | DOOWOP | 6 | R&B genre popular in the 1950s and ’60s |
| 34% | JHERICURL | 9 | *Perm style popular in the 1980s and early 1990s |
| 33% | SPRINGBREAK | 11 | Popular vacation time ... and an explanation of what's straddling the two words in each theme answer? |
| 33% | ASL | 3 | Language in the film "Hear and Now" |
| 33% | UPTOWN | 6 | Like Manhattan in the 80s and 90s? |
| 33% | SPEEDTRAPS | 10 | Things feared in the 80s and 90s? |
| 33% | IDRISELBA | 9 | Actor who was Stringer in The Wire and is now a DJ |
| 32% | PAVEMENT | 8 | Called a sidewalk in the US and trottoir in France |
| 32% | MIXCDS | 6 | Romantic gifts that were popular in the 2000s |
| 32% | HALVA | 5 | Confection popular in South Asia and the Mideast |
| 32% | EWANMCGREGOR | 12 | Actor who played 29-/32-Across in the 1990s and 2000s: 2 wds. |
| 32% | TEEN | 4 | One born in the early 2000s, now |
| 32% | BRO | 3 | Popular term of address among men in the US and New Zealand |
| 32% | MACHINES | 8 | Tiny toy cars made in the 80s and 90s, micro __ |