Toby – Age 61
Don’t let the name fool you; Toby Keith is as American as they come. The singer and songwriter have churned out country anthems for nearly three decades, with tunes that reflect his patriotism and love of America. His latest and nineteenth studio album, Peso in My Pocket, released in 2021, is no exception.
In 1999, Keith, who had been signed to DreamWorks Records Nashville since 1998, dropped his chart-topping hit, How Do You Like Me Now?! Over forty million albums have been sold worldwide as a result of Toby’s 19 studio albums, 2 Christmas albums, and 5 compilation albums. Further, 61 of his singles have reached the Billboard Hot Country Songs charts.