There are some CMA Awards wins you see coming from a mile away when an artist is a shoo-in to take home that glass trophy, but occasionally one will surprise audiences or even make history. Unexpected and iconic victories are part of what makes awards shows exciting, especially on "Country Music's Biggest Night!"

For more than 50 years, the CMA Awards have been doling out honors to country's standout stars, and while all of the recognitions are special, only a handful have been landmark moments to remember for years to come.

We’ve put together a list of 16 of the most important, record-breaking wins from CMA Awards over the decades, each historic in some way. This includes the first African-American (and thus far, the only) winner of Entertainer of the Year, the first woman to win the same honor, and the significance behind Taylor Swift’s wins.

16 Most Iconic CMA Awards Wins Ever:

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