Hans næste album ''[[Country Squire]]'' blev udgivet i maj 2019. Den anden [[Single (musik)|single]] fra albummet, "All Your'n" blev nomineret til en [[Grammy]] for bedste countrysang.<ref>Austin, Emma. (21. november 2019) [https://eu.courier-journal.com/story/entertainment/music/2019/11/21/kentucky-country-artist-tyler-childers-gets-first-grammy-nomination/4257578002/ "Kentucky singer-songwriter Tyler Childers gets his first Grammy nomination"] Courier Journal. Hentet 16. august 2023.</ref> Herefter udgav han ''[[Long Violent History]]'' i 2020, og ''[[Can I Take My Hounds to Heaven?]]'' i 2022.<ref>[https://www.allmusic.com/artist/tyler-childers-mn0003541646/discography "Tyler Childers Albums and Discography"] AllMusic. Hentet 16. august 2023.</ref>
Levende_personer Musik