| SUKIYAKI | Japanese dish, or a 1963 song that topped the Billboard Hot 100 (8) |
| WONDERFUL | How Andy Williams describes Christmas in a 1963 song? It's the Most ___ Time of the Year |
| ABILENE | "Women there don't treat you mean, in ___": Which Texas city is featured in a 1963 song? (7) |
| OLDTOWNROAD | Song that topped the Billboard Hot 100 for a record 19 weeks in 2019 |
| VIDA | Viva la ___ Coldplay's Grammy-winning song that topped the Billboard Hot 100 |
| SONNYBOY | 1928 Al Jolson song that topped the charts for 12 weeks (5,3) |
| UMBRELLA | Rihanna song that topped the charts for ten weeks in 2007 |
| WILLIAMS | Andy, U.S. singer noted for the 1963 song It's The Most Wonderful Time Of The Year (8) |
| PATTYPAN | Central to a Beatrix Potter tale, a dish or tin in which to bake a little pie or cake; or, a miniature scalloped cymling squash, resembling this (8) |
| SUGAR | Watermelon ___ 2020 sweet song by Harry Styles that topped the Billboard Hot 100 |
| COQUILLE | French for "shell", hence seafood served in a scallop's fluted fan-like carapace; a dish or pastry case shaped like said shuck; or, a pat of butter (8) |
| ILLBETHERE | Jackson 5 single that topped the Billboard Hot 100 in 1970 |
| NUMB | 2003 single by Linkin Park that topped the Billboard Hot Modern Rock Tracks chart for 12 weeks |
| ANIMALS | Glass ___ English band who topped the Billboard Hot 100 chart with the song Heat Waves |
| LEPPARD | Def ___ English band who topped the Billboard Hot 100 chart with the song Love Bites |
| ZAYN | British singer who topped the Billboard Hot 100 chart with the song Pillowtalk |
| TAIO | ___ Cruz British singer who topped the Billboard Hot 100 chart with the song Break Your Heart |
| BLUNT | James ___ English singer who topped the Billboard Hot 100 chart with the song You're Beautiful |
| SEAN | Jay ___ British singer who topped the Billboard Hot 100 chart with the song Down |
| LOSEYOURSELF | 2002 Eminem rap song that topped the Hot 100 for a record-tying 12 weeks: 2 wds. |
