Drew Parker 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.

Drew Parker, from Covington, Georgia, shines in country music with hits like Luke Combs’ “Forever After All.” A GRAMMY nominee, he's performed at the Opry and won BMI Song of the Year. His EP “While You’re Gone” topped SiriusXM’s The Highway.