Diamond Rio and Jo Dee Messina

Jo Dee Messina, from Framingham, MA, became a '90s country star with crossover appeal. Known for hits like "Heads Carolina, Tails California" and "Bye Bye," she collaborated with Tim McGraw. Her 1998 album "I'm Alright" made her the first female country artist with three multi-week number ones from a single album. She earned accolades from CMA and ACM and her 2000 album "Burn" went number one. Later, she launched her label, Dreambound Records.

Diamond Rio, formed in 1989, is a Grammy-winning country band known for hits like "Meet in The Middle" and "One More Day." They've sold 6.8M albums, earning six Vocal Group of the Year awards.