Crossword puzzle clue "old time country singer sometimes"

Old-time country singer, sometimes

Grammy nominated singer with the 2015 album "Sometimes I Sit and Think, and Sometimes I Just Sit"

Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds.

"I Was Country When Country Wasn't Cool" singer

Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds.

Country singer Arnold and reggae singer Grant, for two

Country singer Evans or pop singer Bareilles

Country singer with the #1 album and single "Killin' Time" [New Hampshire]