John Michael Montgomery performed his farewell concert, “The Road Home”, on Friday December 12, 2025, at Rupp Arena in Lexington, Kentucky,
I personally hate the end of careers and life. Mainly because it means change, but life changing is the one thing that’s always consistent.
This farewell show marked the end of John’s decades-long touring career that started in 1992. He has had more than 30 singles on the BillboardHot Country Songs charts. This total includes seven number-one singles that include “I Love the Way You Love Me”, “I Swear”, “Be My Baby Tonight”, “If You’ve Got Love”, “I Can Love You Like That”, “Sold (The Grundy County Auction Incident)”, and “The Little Girl”. His two singles “I Swear” and “Sold” were both ranked as the number-one songs on the Billboard Year-End charts for country music in 1994 and 1995, respectively.
His first single, “Life’s A Dance”, was released September 21st in 1992 and only Singles & Tracks (now Hot Country Songs) chart. Country radio should’ve pushed that song to number one, because that’s still one of best songs about life ever released in my opinion.
This final show of John’s was a great big family affair too. It’s featured performances by his brother Eddie Montgomery of Montgomery Gentry, his son Walker Montgomery, and his son-in-law Travis Denning.
He even got a nice permanent surprise thanks to his family and Rupp Arena. They actually hung a John Michael Montgomery banner from the rafters to honor his country music career in his home state of Kentucky.