100. John Denver
Hitting his streak during the war-torn 1970s, John Denver kept things peppy and pleasant, walking the family-friendly line between country, soft folk and easy listening. The man had vices, but he largely kept them out of his songs, choosing instead to glorify the great outdoors in hits like "Take Me Home, Country Roads." Uncool? Perhaps. When Denver was named Entertainer of the Year by the CMA in 1975, presenter Charlie Rich responded by setting fire to the envelope containing Denver's name, which many viewers interpreted as a repudiation of country's pop-friendly crossover. But Denver, with his goofy grin and awww-shucks demeanor, was always content to ride his own Rocky Mountain High, leaving protest music, country classicism and the rock & roll lifestyle to his contemporaries. "I don't mind if they call me the Mickey Mouse of rock," he told Rolling Stone's Chet Flippo in 1975. His fans didn't mind, either, and by the decade's end, Denver had racked up nine Number One hits on multiple charts. His influence on country music remains apparent – decades after its release, "Country Roads" was the backbone of 2016's "Forever Country," a mash-up celebrating the CMA Awards' 50th anniversary. Andrew Leahey
Key Tracks: "Take Me Home, Country Roads," "Thank God I'm a Country Boy"