| BILLYRAYCYRUS | Achy Breaky Heart country singer who collaborated with rapper Lil Nas X on Old Town Road in 2019: 2 wds. |
| LILNASX | Rapper who released 'Old Town Road' in 2018 (3,3,1) |
| ACHY | "___ Breaky Heart"; country song |
| OLDTOWNROAD | Single by American rapper Lil Nas X that in 2019 became the longest-running No 1 in US chart history (3,4,4) |
| BILLY | With 8-Across, Cyrus on "Old Town Road" |
| GEORGESTRAIT | I Cross My Heart country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| MATTEA | "Come From the Heart" country singer Kathy |
| JASONALDEAN | Got What I Got country singer who collaborated with rapper Ludacris on Dirt Road Anthem (Remix) in 2011: 2 wds. |
| TAYLORSWIFT | Fearless country singer who collaborated with rapper B.o.B on Both of Us in 2012: 2 wds. |
| MERLEHAGGARD | Country singer who collaborated with Willie Nelson on the 2015 album "Django and Jimmie" |
| DOLLYPARTON | Jolene singer who collaborated with Brad Paisley on the 2005 country hit When I Get Where I'm Going: 2 wds. |
| ALISONKRAUSS | When You Say Nothing At All singer who collaborated with Brad Paisley on the 2004 country hit Whiskey Lullaby: 2 wds. |
| JIMMIEALLEN | Best Shot singer who collaborated with Brad Paisley on the 2021 country hit Freedom Was a Highway: 2 wds. |
| THEWEEKND | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| EDSHEERAN | Singer who collaborated with Beyonce on the 2017 #1 hit Perfect Duet: 2 wds. |
| CYRUS | Which singer (Billy Ray _) topped the charts with "Achy Breaky Heart" in 1992? (5) |
| RAYCYRUS | Achy Breaky Heart singer who stars in Mulholland Drive, Billy ___ |
| TONYBENNETT | US singer who collaborated with Lady Gaga on the 2014 album Cheek to Cheek (4,7) |
| CABALLE | Opera singer who collaborated with Freddie Mercury on the song Barcelona (7) |
| ESTELLE | British singer who collaborated with Kanye West on the 2008 hit "American Boy" |
