The most popular radio format in the United States, country music is nothing to scoff at. It has the largest and most loyal fan base, also making it one of the most demanding and critical of multi-genre crossover. So why have so many pop artists and rock stars made the attempt to build a bridge to troubled waters? Plenty of popular musical artists have Southern- or country-influenced pasts, but it takes guts and confidence to make a move from pop/rock to country and back again. In this hot gallery, find out which big-name artists scored a hit, both with fans and on the country music charts!

Each year the Grammys give an award for Best New Artist, which must be taken as loosely as possible because many are not the best, and some aren’t even really new. We’re looking back at some of these winners and the inspired (but mostly uninspired) careers they have had since.