Jason Aldean has built one of the biggest careers in contemporary country music, but it all started with his first No. 1 hit more than a decade ago. Do you remember the first song that took him to the top of the charts?

Aldean had a long journey to finally getting a record released, but he didn't have to wait long for success to strike once he got his music out there. His debut single, "Hicktown," became a Top 10 hit, and he scored his first No. 1 single with its follow-up, "Why." The song reached the top of the Billboard Hot Country Songs chart on May 27, 2006.

Rodney Clawson, Vicky McGehee and John Rich from Big & Rich co-wrote "Why." which was a stark contrast to the high-voltage party vibe of "Hicktown." The mid-tempo ballad finds an introspective Aldean realizing that he has caused his lady love great pain, and asking himself why he treats her the way he does and so often fails to show his true feelings for her.

"Sometimes I wonder why / Does it always have to come down to you leaving / Before I'll say 'I love you' / Why do I always use the words that cut the deepest / When I know how much it hurts you / Oh baby why do I do that to you," Aldean sings in the chorus.

The third single from Aldean's self-titled debut album, "Amarillo Sky," also became a smash hit, landing at No. 4 on Billboard's Hot Country Songs chart, and Aldean was launched on a trajectory that would see him become one of the biggest hitmakers and headliners in country music.

See Inside Jason Aldean's Spectacular Florida Beach House

Jason Aldean's beach house in Santa Rosa, Fla., sits right on the Gulf of Mexico.

Aldean paid $4.1 million for the new 5-bedroom, 5-bathroom, 4,452-square-foot beach house. The spectacular property affords the singer and his family the opportunity to walk out their back door and down a bridge to their own private beach, and the exterior of the villa features a courtyard with iron gates that includes gas lanterns, a swimming pool and a fountain.

The home's interior includes a downstairs with an open floorplan and oversized windows, chiseled stone floors, a gourmet kitchen, a bedroom and study and a fireplace, with coffered ceilings throughout. The upstairs of the home includes two separate master bedrooms that both overlook the Gulf, as well as two more bedrooms that each have their own attached bathrooms.

The stunning home is also set for whatever weather might blow in from the Gulf. Built in 2005, the house features all-impact windows and doors, as well as Geo-Thermal heating and cooling, cellulose insulation, foam ceiling and floor insulation and more.

Top 50 Jason Aldean Songs: His Greatest Hits + Best Deep Cuts

The best Jason Aldean songs are spread out among his 11 studio albums. Find singles and deep cuts from his self-titled debut album high on this list, right alongside more recent hits and duets from Macon and Georgia.

Taste of Country asked readers for input and did a deep dive into Aldeans' full catalog of songs to identify those worthy of this top songs list, and those that simply aren't. Spoiler alert: A few radio singles are missing, and several album tracks rank inside the Top 20. Sales and chart success helped us round out the Top 50. Do you agree with No. 1?

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