Toby Keith’s 25 Best Songs Prove He’s Hall of Fame Worthy
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Toby Keith’s 25 Best Songs Prove He’s Hall of Fame Worthy

Narrowing down Toby Keith‘s Top 25 songs is no easy job. He was able to effectively cover a variety of topics since he made his debut in 1993.

Keith could be a rabble-rouser, a balladeer or a good-time partier, depending on which tune you choose. Plus, he wrote at least two of the all-time greatest patriotic songs. Very few artists could claim hits over such a long stretch of time, though.

During a 30-plus year career, Keith notched 20 No. 1 hits on the Billboard Country Airplay chart. His last chart-topper was “Made in America” in 2011, but in the decade since, he released important radio songs like “Don’t Let the Old Man In.”

A performance of that song at the 2023 People’s Choice Country Awards brought fans and family to tears. The singer himself even teared up singing the powerful — and suddenly relevant — ballad.

These 25 Toby Keith hits were selected using a combination of factors, including chart position, sales figures, ToC staff opinions and readers’ feedback. Read on to find out what made the cut and click on any of the links to listen.

Toby Keith’s 25 Best Songs Prove He’s a Country Icon

Toby Keith reached No. 1 on the Billboard Country Airplay chart 20 times during his 30-plus year career, but some of this best songs were deep cuts.
Here are his greatest hits — the top songs from 19 studio albums and beyond.
Toby Keith died on Feb. 5, 2024 after a two-year battle with stomach cancer.

No. 25: “Red Solo Cup” (From ‘Clancy’s Tavern,’ 2011)

Nope, “Red Solo Cup” is not one of Toby Keith’s best, but admit it: A list without this playful jaunt would be incomplete.
No. 24:

No. 24: “Whiskey Girl” (From ‘Shock’n Y’all,’ 2003)

Toby Keith dropped “Whiskey Girl” after hitting No. 1 with “Beer for My Horses,” “I Love This Bar” and “American Soldier,” and the new single climbed that mountain with ease.
WWE star Amy Weber was the “Whiskey Girl” in a music video that’s not likely to avoid criticism in 2024. The objectifying nature of the song and video passed then, but it’s worth noting that Keith’s career would hit a lull in the two to three years that followed.

No. 23: “Me Too” (From ‘Blue Moon,’ 1996)

“Me Too” is an often forgotten hit for Toby Keith, but the song reached No. 1 in 1997. It’s a tender ballad is a lyrical showcase that he likely wrote hoping for a great anniversary song. It’s easy to imagine him struggling with the same three words his protagonist struggles with, so for that reason it’s very believable.

No. 22: “Who’s Your Daddy?” (From ‘Unleashed,’ 2002)

“Who’s Your Daddy” is a signature Toby Keith song, among his very best. It’s got the attitude and sense of humor that would define his career, and it was a little controversial. That’s Toby, right?
No. 21:

No. 21: “American Ride” (From ‘American Ride,’ 2009)

“American Ride” is best remembered for the JibJab style music video that seemed to make a social or political statement. Immigration, climate change, loss of religion and more are referred to here, but through it all the singer states with conviction that he loves this American ride.

No. 20: “Made in America” (From ‘Clancy’s Tavern,’ 2011)

A decade after dropping two patriotic songs, Toby Keith released another as the economy rebounded. “Made in America” rides along a thick rock track. It was his final No. 1 song.

No. 19: “She Never Cried in Front of Me” (From ‘That Don’t Make Me a Bad Guy,’ 2008)

Toby Keith sounded a bit different on “She Never Cried in Front of Me,” his arena rock ballad from 2008. Co-writer Bobby Pinson shares that they wrote it on piano, which was unusual. It hit No. 1 and deserves a spot on this list of his top songs.

No. 18: “Love Me If You Can” (From ‘Big Dog Daddy,’ 2007)

Songs like “Love Me If You Can” reveal the nuance in Keith’s personality. He didn’t write the reflective ballad, but in recording and releasing the chart-topper, he recognized how his opinions and actions might offend some.
“Hate me if you want to / Love me if you can,” he sings to close each chorus.

No. 17: “Who’s That Man” (From ‘Boomtown,’ 1994)

“Who’s That Man” is a classic Toby Keith breakup song. The singer finds that another man has taken his place in the lives of his (ex) wife and kids, and he’s pretty blue about it. Keith wrote this No. 1 hit by himself, something he’d do often during his career.

No. 16: “I Love This Bar” (From ‘Shock’n Y’all,’ 2003)

“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 20 list. Critics were right when they predicted that this song would become a barroom anthem for years to come.

No. 15: “God Love Her” (From ‘That Don’t Make Me a Bad Guy,’ 2008)

Toby Keith does Southern rock on “God Love Her,” a No. 1 hit from 2009. The uptempo hit is a coming-of-age story focused on two young lovers. It relies on a powerful, memorable chorus and some nasty guitar work.

No. 14: “Beer for My Horses” (From ‘Unleashed,’ 2002)

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.

No. 13: “Upstairs Downtown” (From ‘Boomtown,’ 1994)

The story goes that Toby Keith didn’t love “Upstairs Downtown” as a radio single, but we sure did. The ballad from Boomtown is a true country circle-of-life story that showed a new side to the hitmaker.

No. 12: “I’m Just Talkin’ About Tonight” (From ‘Pull My Chain,’ 2001)

The descending melodic structure of “I’m Just Talkin’ About Tonight” is the charm of this chart-topper. It’s no-nonsense story set atop a honky-tonk beat and it’s one of Toby Keith’s greatest hits.

No. 11: “My List” (From ‘Pull My Chain,’ 2001)

Toby Keith’s love song from 2001 took on a new meaning when he set the music video to memories of the September 11 attacks. The soft, acoustic cut is timeless country music and an easy choice for this list of his best songs ever.

No. 10: “I Wanna Talk About Me” (From ‘Pull My Chain,’ 2001)

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.

No. 9: “You Shouldn’t Kiss Me Like This” (From ‘How Do You Like Me Now?!,’ 1999)

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 20 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.

No. 8: “A Woman’s Touch” (From ‘Blue Moon,’ 1996)

“A Woman’s Touch” is an under-appreciated song from Toby Keith’s catalog. The production is a bit outdated in 2024, but his warm voice still quiets the heart.

No. 7: “American Soldier” (From ‘Shock’n Y’all,’ 2003)

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.
Cover of Toby Keith's Honkytonk University album

No. 6: “As Good as I Once Was” (From ‘Honkytonk University,’ 2005)

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.

No. 5: “How Do You Like Me Now?” (From ‘How Do You Like Me Now?,’ 1999)

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.

Cover of Toby Keith's American Ride album

No. 4: “Cryin’ for Me” (From ‘American Ride,’ 2009)

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 20 Toby Keith Songs list.

No. 3: “Should’ve Been a Cowboy” (From ‘Toby Keith,’ 1993)

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.

Picture of Toby Keith performing

No 2: “Don’t Let the Old Man In” (From ‘Greatest Hits: The Showdog Years,’ 2019)

You could make an argument for “Don’t Let the Old Man In” as Toby Keith’s very best song, but we’ll not decide these kinds of things while grieving. The ballad was written and recorded for The Mule, a movie starring Keith’s friend Clint Eastwood. It took on a new meaning when — amid his cancer battle — he performed it at the 2023 People’s Choice Country Awards.

No. 1: “Courtesy of the Red, White and Blue” (From ‘Unleashed,’ 2002)

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 20 Toby Keith Songs.
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