21 Best Toby Keith Songs

Toby Keith has enjoyed a long and storied career as a country musician, releasing hit after hit for decades. Here are the best Toby Keith songs ever.

1. “As Good As I Once Was” by Toby Keith

Song Year: 2005

“As Good As I Once Was” was the second single from Honkytonk University. It’s a funny take on aging with lyrics about a guy who may not be as young as he used to be, but still has some fight left in him. Keith wrote it with frequent collaborator Scotty Emerick, and it was another number-one hit.

Willie Nelson appears in the video, so apparently he and Keith had a good time on “Beer for My Horses” a couple of years earlier.

2. “I Love This Bar” by Toby Keith

Song Year: 2003

“I Love This Bar” is something like country music’s version of the Cheers theme song. It’s an ode to a honky-tonk bar, the narrator’s local watering hole. If you have your own neighborhood bar, you understand what an important part of life that can be.

The lyrics describe the bar’s quirky patrons and the good times to be had there. It was based on a real-life Nashville joint called Tootsie’s Orchid Lounge, and the song has become so synonymous with Keith that he named his own franchise of bars “Toby Keith’s I Love This Bar & Grill.” Toby Keith has never been accused of subtlety.

3. “Red Solo Cup” by Toby Keith

Song Year: 2011

It’s hard to think of a party anthem as fun as “Red Solo Cup,” from Clancy’s Tavern. It’s a fun song about the red plastic cups that are the backbone of any great party, whether it’s on a college campus or in a backyard.

“Red Solo Cup” was a big hit, and the catchy tune is one of those songs you end up singing to yourself for several days after hearing it once. Whether that’s a feature or a bug depends on whether you’re a Toby Keith fan, one would suppose. And yes, that’s Sammy Hagar making a cameo in the video.

4. “How Do You Like Me Now?!” by Toby Keith

Song Year: 1999

The lead single from Toby Keith’s album of the same name, “How Do You Like Me Now?!” is a defiant anthem about a man who’s made it in life and wants to make sure that his unrequited love, the woman who never noticed him (the head cheerleader and valedictorian), knows all about it. It’s yet another hit of Keith’s that he wrote (or, in this case, co-wrote), which is a big deal—many country stars don’t write their own songs.

The iconic Rolling Stones song “(I Can’t Get No) Satisfaction” served as inspiration for the guitar riff that became the number-one hit and earned Keith a CMA Award for Music Video of the Year.

5. “Courtesy of the Red, White and Blue (The Angry American)” by Toby Keith

Song Year: 2002

“Courtesy of the Red, White and Blue (The Angry American)” signaled Toby Keith’s pivot to patriotic themes in his music, and it expressed the collective rage Americans felt following the September 11 attacks.

It is an unapologetically direct song and a defiant call to arms, and many Americans adore this song. It won the Academy of Country Music Award for “Song of the Year.”

6. “Should’ve Been a Cowboy” by Toby Keith

Song Year: 1993

Toby Keith’s “Should’ve Been a Cowboy” was a number-one single. It also crossed over to number 93 on the Billboard Hot 100, so he was obviously onto something with the sound.

The song is about a man who wishes he was a cowboy in the Old West, living a life of adventure and romance. He imagines riding the range, breaking horses, and winning the love of a good woman. It was the most-played country song of the 1990s.

7. “Beer for My Horses” by Toby Keith

Song Year: 2003

The duet “Beer for My Horses” by Keith and country legend Willie Nelson from Keith’s album Unleashed is allegedly based on a Robin Williams comedy routine.

Williams riffed about sending country singers instead of soldiers into war zones, the joke being that they could get stuff done. Keith extrapolated that idea into “Beer for My Horses,” a tune about the Old West and a fun country song. It was one of Keith’s 20 number-one hits. Willie Nelson’s presence probably helped.

8. “She Never Cried in Front of Me” by Toby Keith

Song Year: 2008

Since so many songs are about heartbreak and loss, we can’t get very far on any kind of song list without having one of them show up. A man grieving over a relationship’s abrupt end is the subject of the heartbreaking ballad “She Never Cried in Front of Me.”

Toby Keith is known for his ability to convey emotion in his performances (among other things), and “She Never Cried in Front of Me” is a prime example of this delivery. It has become one of his most beloved songs.

9. “God Love Her” by Toby Keith

Song Year: 2008

Strong women are the characters in a lot of country music, but they often appear in songs sung by female artists. “God Love Her,” though, finds Toby Keith singing about a woman living on her own terms in the face of judgment from others. Her parents catching her with the narrator cemented her reputation as a troubled woman with the people around her.

The song about being an individual struck a chord with fans and became a top-ten hit. Supposedly, a fan Keith encountered at one of his live performances served as inspiration.

10. “Love Me If You Can” by Toby Keith

Song Year: 2007

“Love Me If You Can” was the lead single from Toby Keith’s album Big Dog Daddy. It’s a call for compassion and understanding in a world that can be harsh and unforgiving. There are hints in it of Keith’s ardent support for the US military, but the main thrust of the song is that empathy and kindness are good things that we all could use more of.

The song came several years after some backlash from Keith’s post-9/11 hit “Courtesy of the Red, White,Man? and Blue (The Angry American)” and finds the singer explaining his side of things. He maintains that he is who he is, and if you like him, great. If you don’t, that’s on you.

11. “Who’s That Man” by Toby Keith

Song Year: 1994

Toby Keith tells of a man who returns home to find that his wife has moved on and is with someone new. He recognizes his wife, his house, and his kids, but he spends the entirety of the song trying to identify the one thing in the picture he can’t place—the man who isn’t him.

It ain’t exactly a happy song, but it was an early top-ten country hit for Keith and set him on a path to superstardom.