The 10 Best Toby Keith Songs of All-Time

When Toby Keith first rode into Nashville in the early 1990s, no one paid any attention. After trying and failing to win a record deal, he cut his losses and headed home. But then a flight attendant and fan of his handed a copy of his demo to Harold Shedd at Mercury during a flight. A short time later, Toby Keith was back in Nashville with a record deal in one hand and a notebook of lyrics in the other. Since then, his well-crafted ballads, rowdy drinking anthems, and witty novelty songs have turned him into one of country’s biggest stars. Here’s our pick of the 10 best Toby Keith songs of all time.

10. Red Solo Cup

 

Kicking off our list of the ten best Toby Keith songs of all time is a song that Keith described to as “the stupidest song I ever heard in my life, but it’s so stupid it’s good.” Written by the Warren Brothers and Brett and Jim Beavers, Red Solo Cup might be the silliest song in Keith’s repertoire, but it’s also his biggest selling hit, with over two million sales to date.

9. My List

 

Keith is as much a writer as he is a singer, but this next song is one of the few that he relied on outside help for. Written by Tim James and Rand Bishop, My List tells the story of a man who finally decides to stop working through his list of chores and make more time for his family and “start living — that’s the next thing on my list.” Released as the final single from Keith’s 2001 album Pull My Chain, the song topped the Billboard Hot Country Songs chart for five weeks and peaked at number 26 on the Billboard Hot 100.

8. Cryin’ for Me (Wayman’s Song)

 

Keith wrote Cryin’ for Me (Wayman’s Song) as a tribute to basketball player and jazz musician Wayman Tisdale following his death in May 2009. Dave Koz’s saxophone provides a wonderful accompaniment to the tender song, which ranks among the subtlest and most poignant in Keith’s catalog. Released as a single in October 2009, it gave Keith a top ten hit on the country charts.

7. Upstairs Downtown

 

He might be best known for his blue-collar drinking anthems, but Keith also knows his way around a ballad. On this early hit from the 1994 album Boomtown, he turns the spotlight on a young woman desperate to leave ‘the woods’ and forge her own path in the city. She finally gets her own apartment and a job, but soon discovers that living away from her family is harder than she thought. After she loses her job and struggles to keep up with her bills, she decides to turn her back on the city and go home.

6. Beer for My Horses

 

If you’re going to invite a legend like Willie Nelson to duet with you, you’d better make sure that song is worth the paper it’s written on. Fortunately, Beer For My Horses is a cracker. Written about a group of vigilantes who come together to fight injustice then order ‘whiskey for my men, beer for my horses,” it combines Keith’s trademark humor with lines like “We’ll raise up our glasses against evil forces”, which, coming as they did in the wake of the 9/11 attacks, took on a new level of poignancy. Released as a single from the album Unleashed, it hit number 22 on the Billboard Hot 100 and topped the country charts for a mighty 6 weeks.

5. As Good As I Once Was

 

Described by Sputnick as “a testament to how much old age sucks,” As Good As I Once Was finds the aging narrator going to a bar and putting himself through various trails that test his masculinity before ruefully concluding “I ain’t as good as I once was … that’s just the cold, hard truth.” Released in May 2005, the song spent six straight weeks at number one on the country charts and picked up the award for BMI’s Song of the Year.

4. I Love This Bar

 

In 2003, Keith earned another massive hit with this good time beer joint staple from his 2003 album, Shock’n Y’all. Co-written alongside Scotty Emerick, I Love This Bar spent 5 consecutive weeks at the top of the US Billboard Hot Country Single and Tracks chart and reached number 26 on the Billboard Hot 100. It also ended up inspiring the name of Keith’s restaurant chain, Toby Keith’s I Love This Bar & Grill.

3. Courtesy of the Red, White and Blue (The Angry American)

 

9/11 inspired countless heartfelt songs that dealt with the events from a sentimental, tragic perspective, but none that dealt with the anger many Americans felt once the initial wave of fear and sadness had passed… none, that is, until Keith recorded Courtesy of the Red, White and Blue (The Angry American). Written as a tribute to his recently deceased father, a veteran whose patriotic faith in his country had inspired Keith’s own, it was a song whose strong sentiment divided as much as it united, leading to both a heap of controversy and another number one hit for Keith.

2. Should’ve Been A Cowboy

 

If you’ve ever wondered what the most played country song of the 1990s was, cast an ear in the direction of this next song. Released in February 1993 as his debut single, Should’ve Been A Cowboy stormed to number one on the US Billboard Hot Country Songs and the Canadian RPM Country Tracks charts, established Keith as the hottest new talent on the scene, and picked up more than 3 million songs on country radio.

1. How Do You Like Me Now?!

 

Discussing the inspiration behind How Do You Like Me Now?!”, Keith has said “Initially, I said, ‘Here’s my title: “You Never Loved Me Before, So How Do You Like Me Now?'” It’s one of my catchphrases. A lot of people become successful after they’ve been told they won’t ever be, so people can relate to this. It can be about an old flame or a boss or a teacher -whatever it means to each individual. It was a fun song to write.” Everyone loves a story about an underdog making good, especially when it’s wrapped in a feisty performance and infectious melody. Released in November 1999, the song soared to number 1 on the country chart, number 31 on the Hot 100, and picked up nominations for Single of the Year and Song of the Year at the Academy of Country Music awards.