It was “19(90) Somethin’” when Grand Ole Opry member Mark Wills went from singing at Atlanta’s infamous Buckboard to releasing his first of 19 Billboard-charting singles across seven albums. While climbing his musical ‘ladder,’ he has recorded Gold and Platinum albums and released some of the most enduring and recognizable Country Music hits of the last 25 Years.

“Wish You Were Here,” “Jacob’s Ladder” and “I Do (Cherish You)” cemented his country status in the late ’90s and at the ‘dawning of a new decade’ in the early ’00s. “Jacob’s Ladder” was released via Mercury Nashville in May 1996 as Wills’ debut single, and it became the singer’s first of eight Top 10 hits. His debut self-titled album followed “full of rambunctious good-time songs teeming with sly wit and bittersweet ballads — all in a baritone that throbs with emotion” per Entertainment Weekly. Released 20 years ago as part of Wills’ Greatest Hits collection, the feel-good track stretched the singer both musically and vocally. Billboard Hot Country Songs chart Top 5 hits “Places I’ve Never Been,” “I Do (Cherish You),” “Don’t Laugh at Me,” and No. 1 single “Wish You Were Here” hit the airwaves between 1997-1999. Fittingly, Wills’ early chart success earned him an Academy ofCountry Music Award for Top New Male Vocalist in 1998. One of his biggest hits to date is the RIAA Gold-certified “19 Somethin’” – a six-week No. 1 on the Billboard Hot Country Songs chart.