Annie Zaleski

The idea that country's bad boy was settling down was a surprise to many — including Tritt himself.

Do y'all agree?

The New Jersey native dominated the genre charts in the late 1980s and into the '90s, thanks to a streak of records that featured insightful reflections on love, politics and the human condition.

During the week of Feb. 15, 2014, "Drink a Beer" began its five-week reign atop the Billboard Hot Country Songs chart.

Is your favorite on the list?

Here are 20 country No. 1 hits that double as tangible proof that chart success isn't the only way to measure greatness.

On June 30, 1993, Chesney signed his first record deal, with the newly opened country division of Capricorn Records.

On June 29, 1968, Wynette hit No. 1 on the U.S. country charts with "D-I-V-O-R-C-E."

On June 18, 2013, Bradbery emerged as the winner of Season 4 of 'The Voice'.

On June 6, 1980, 'Urban Cowboy' hit theaters.

Do y'all agree?

On May 27, 2008, Darius Rucker released his debut country single, "Don't Think I Don't Think About It."