Willie Nelson gave Keith’s career a big old stamp of approval by joining him on this hit from 2003. The song would become a six-week chart topper and later be turned into a movie. The surprising thing about this hit, one of our top Toby Keith songs, is that most people didn’t understand the concept of giving beer to one’s horses after a job well done. To be honest, most people under the age of 100 still don’t totally comprehend the idea, but it was funny, so it works.

Keith’s debut single not only went straight to No. 1, it also became the most-played song of the ’90s. “Should’ve Been a Cowboy” began a career that would become one of the most successful in country music history. The song is still heard on country radio stations across America today, and it was never uncommon for Keith to bring it to his live show. Ironically, many thought the singer was very much a cowboy 10 years later, when he feuded with Peter Jennings and the Dixie Chicks.

Including this song over ballads like “My List” and “Who’s That Man” is purely a matter of opinion — in this case, staff opinion. One could make a case for any of these three songs on this list of the Top 10 Toby Keith songs, as they were all wildly successful, and they all were unexpectedly tender performances from the rough and tough country star. While he’ll be remembered for rowdy hits like the top two songs on this list, he would never have lasted two-plus decades without being capable of singing a convincing ballad.

Keith and Scotty Emerick wrote some of the singer’s most entertaining songs, including this hit from 2005. It spent six weeks atop the country charts and sold a ton of singles and albums. The story is one anybody over the age of 30 can relate to — a slightly self-deprecating lyric that couldn’t have come at a better time for a singer who some felt was beginning to take himself a little too seriously.

This four-week chart topper from Shock’n Y’all still resonates among the families of the men and women who serve this country in the armed forces. While many songs about America’s military or political climate felt disingenuous at the time, Keith seemed to sing from the perspective of a man who’d not only been to the Middle East, but had gotten to know the ins and outs of day-to-day military life. Fifty years from now, this song will still get airplay over the Memorial Day and Fourth of July weekends, so it’s a shoo-in for our list of the best Toby Keith songs.

This song was controversial in 2001, as many wondered if the pacing and rhythm were too close to rap music. Blake Shelton originally cut the record, but he didn’t release it because his label felt it’d be too risky for a debut single. Keith joked to Billboard that no one who did rap would call it rap, though, and he was right: It went on to become his seventh No. 1 hit.

After eight years of hits and misses, Keith really began to find his swagger during the early 2000s. A number of songs come loaded with an attitude that would define his best-known hits. It’s that chip on the shoulder that made him so easy to relate to as an artist.

Beginning in 1999, Keith put up No. 1 hits like Michael Jordan put up layups. Eleven of 13 songs topped the country chart, including this title track from the How Do You Like Me Now?! album. He needed the lift, as previous singles had failed to attract attention from fans or radio (“When Love Fades,” anyone?). This one’s not only a great story about the underdog having his moment to throw success in the face of all who’ve doubted him, it’s also a song that re-energized Keith’s career. One could argue it’s the most important Toby Keith song that’s been released, if not the best.

With “Cryin’ for Me,” it felt like, for the first time in six years, they had a song that peeled the curtain back on Keith’s soul. The track was written after Keith’s dear friend Wayman Tisdale died, and after a string of more disposable singles like “She’s a Hottie,” this song felt like a jolt of honesty. Early in Keith’s career, it was easy to find examples of this sort of emotion, so even though this song didn’t top charts or sell a million singles, its artistic merits are enough to clear a spot on our Top 10 Toby Keith Songs list.

“I Love This Bar” both spent five weeks atop the Billboard country charts and launched a successful restaurant chain for the country superstar. Looking back, songs from Unleashed and Shock’n Y’all represent the peak of Keith’s career: They resulted in six No. 1 hits, including four that made their way onto this Top 10 list. Critics were right when they predicted that this song would become a barroom anthem for years to come.

The best songs come quickly, and this career-defining hit from Toby Keith is said to have taken only 20 minutes to write. Keith was inspired by the death of his father and the Sept. 11, 2001, terrorist attacks, and the very first time he performed “Courtesy of the Red, White and Blue” at a live show, fans went nuts. It went on to become his biggest hit on the Billboard Hot 100 chart, his first Gold single and, now, the No. 1 tune on our list of the Top 10 Toby Keith Songs.