Kenny Rogers has had quite the career.
Having charted more than 120 songs in a career that dates back to 1976, country radio pretty much forgot about the man they call The Gambler after his last big hit, “The Vows Go Unbroken (Always True to You),” peaked at No. 8 in 1987. He had a series of hits after that, but aside from 1991’s “If You Want To Find Love,” they never made it far on the charts.
Like every good gambler, Kenny had one last good hand to play, and that came in 2000 with “Buy Me A Rose.” With the help of Alison Krauss and Billy Dean, Kenny played his final winning hand as the song went to No. 1 in May of that year.
Not only was it Kenny’s last No. 1 hit, but it was also the only chart-topper for Billy Dean and Alison Krauss (her smash “When You Say Nothing At All” peaked at No. 3). In addition to that, being 61 years old at the time “Buy Me A Rose” was released, it made Rogers the oldest singer to have a No. 1 hit on the country charts, which is a record he would hold until 70-year-old Willie Nelson took it away three years later by dueting with Toby Keith on the chart-topping “Beer For My Horses.”