Country singer John Michael Montgomery began performing with his parents at age five and later joined a band with his brother and a friend, who would go on to form the duo Montgomery Gentry. ∙ “I Love the Way You Love Me,” from his 1992 debut, Life’s a Dance, won Song of the Year and earned him Top New Male Vocalist honors at the American Country Music Awards. ∙ In 1994, the crossover smash (and popular wedding song) “I Swear” topped Billboard’s Year-End Country chart, and it earned the R&B group All-4-One a Grammy Award the following year. ∙ Montgomery’s self-titled 1995 album went quadruple-Platinum with the help of “I Can Love You Like That,” a chart-topping romantic ballad that also landed All-4-One in the Top 10. ∙ He swapped pop balladry for a return to his country roots in 2002, earning a No. 1 hit with “The Little Girl,” a tear-jerker duet with bluegrass artist Alison Krauss. ∙ Proving the staying power of the family business, his son, Walker Montgomery, went viral in 2017 with the single “Simple Town.”