| SIXTEEN | Song from Thomas Rhett's Life Changes album that topped the Country Airplay charts in 2019 |
| UNFORGETTABLE | Song from Thomas Rhett's Life Changes album that topped the Country Airplay charts in 2017 |
| MARRYME | Song from Thomas Rhett's Life Changes album that topped the Country Airplay charts in 2018: 2 wds. |
| JUSTINBIEBER | Pop/R&B singer who's also topped the Country chart, thanks to 10,000 Hours with Dan + Shay: 2 wds. |
| ITONA | Thomas Rhett's "Blame ___ Backroad" |
| HEARTBREAKER | 1978 Dolly Parton song from the eponymous album that topped the U.S. country singles chart |
| THEGITUP | Blanco Brown song that spent 12 weeks atop the Hot Country charts in 2019: 3 wds. |
| WATERMELONSUGAR | Song by Harry Styles that reached No. 4 in the UK charts in 2019 (10,5) |
| THOMASRHETT | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| GOTYE | His Somebody That I Used to Know topped both the Hot 100 and Alternative Airplay charts |
| NICO | "The Velvet Underground & ___" (1967 album that topped Billboard's list of the best album covers of all time in August, 2023) |
| HOZIER | Irish act whose album Wasteland, Baby! topped the US charts in 2019. (6) |
| PARALLEL | 1978 Blondie album that topped the UK charts, _ Lines (8) |
| GLASSANIMALS | Their Heat Waves topped both the Hot 100 and Alternative Airplay charts: 2 wds. |
| LORDE | Her Royals topped both the Hot 100 and Alternative Airplay charts |
| BILLIEEILISH | Her Bad Guy topped both the Hot 100 and Alternative Airplay charts: 2 wds. |
| FARFROMTHEMADDINGCROWD | Thomas Hardy novel whose title comes from Thomas Gray's poem Elegy Written in a Country Churchyard |
| MARIAHCAREY | Her 2009 hit Obsessed reentered the Billboard charts in 2019 thanks to a viral dance challenge video: 2 wds. |
| JONASBROTHERS | Pop trio whose Like It's Christmas topped the Adult Contemporary chart in 2019: 2 wds. |
| SHAWN | _ Mendes, topped the chart in 2019 with Senorita (5) |
