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Remembering and Honoring Toby Keith Through 16 Of His Best Songs

Raise your “Red Solo Cups” up in the air in honor of the late, great country superstar

The country music world lost one of its biggest and boldest talents on February 5, 2024 when Oklahoma’s own Toby Keith passed away at age 62 after a hard-fought battle with stomach cancer. Never one to mince words or back down from a challenge, Keith had been back out on the road singing his beloved songs, despite his diagnosis.

“Been on the old rollercoaster, but Almighty’s riding shotgun,” Keith announced, with a nod to his faith, in a video he posted promoting some recent shows in late 2023. “Through COVID and cancer, the old devil’s been after me a little bit. I’ve got him by the horns right now, so instead of just sitting around and waiting, we’re gonna get the band back together,” he continued.

Now the fans who were elated to have him back are devastated that his ride was tragically cut short. “Saddle up the horses, Jesus, ’cause a true blue COWBOY just made his ride up to heaven!!! Introduce him to all the Okies and sign that boy up for the choir,” fellow Okie Carrie Underwood posted in Keith’s honor after his passing.

Country legend Tanya Tucker added, “He was so kind and his music meant so much. He was so patriotic, loved his country and loved his fans!! He was a great warrior right up until last night. Now he’s in God’s army.”

Toby Keith singing; Toby Keith Songs
Toby Keith (2021) Matt Winkelmeyer / Staff / Getty

Toby Keith, a two-time ACM Entertainer of the Year and the recipient of 2023’s Country Icon Award at the People’s Choice Country Awards, will also be remembered for his numerous USO performances of songs for the men and women serving in our armed forces overseas.

In 2021, he even won the National Medal of Arts, the highest award given to artists by the U.S. government. As John Rich of Big & Rich posted of the impact of Keith’s loss, “He was a true Patriot, a first class singer/songwriter, and a bigger than life kind of guy. He will be greatly missed.”

Keith, a 2015 inductee into the Songwriters Hall of Fame, of course, leaves behind a truckload of hits from albums that had sales of more than 40 million throughout his four-decade career.

Here, a roundup of the best Toby Keith songs to remember the unflinchingly original country star.

16. “American Ride” (2009)

Though this wasn’t a tune he penned himself, Keith did help massage the title of the track from “American Life” to “American Ride,” with the permission of songwriters Joe West and Dave Pahanish. “It’s like we’re on this roller-coaster with all this stuff going on,” Keith noted of the hot-topic issues and current events listed in the lyrics. Though the track didn’t wow every critic, “it was a monster hit,” Keith pointed out, adding, “I played it every night in [my] show.”

15. “Who’s Your Daddy” (2002)

“It’s everything that I ever wanted to put into a song,” the artist said of this tune, which perfectly showcases his unique brand of country cheekiness. “It’s got the groove, it’s got the attitude, it’s humorous, it’s about a sugar daddy. And it’s got a real funny little Elvis thing in it, like Viva Las Vegas … it’s got a New Orleans piano in it.” Pure fun, and definitely one of the best Toby Keith songs to groove to.

14. “Don’t Let the Old Man In” (2018)

A golf event with Clint Eastwood led to the artist writing this pensive track, which is one of the best Toby Keith songs. “[Clint] was turning 88” at the time, the singer noted of playing with Eastwood, who was about to start a new film in a few days.

“And I just said, ‘What keeps you going?’ And he says, ‘I try not to let the old man in.’” Keith wrote a song based off that line, and sent it to Eastwood, who liked it so much he put it in that new film he was working on, The Mule. “Many moons I have lived / my body’s weathered and worn. Ask yourself how old you’d be / If you didn’t know the day you were born. Try to love on your wife and stay close to your friends / Toast each sundown with wine / Don’t let the old man in,” Keith sings on this beautiful song, which is even more poignant than ever after his death.

13. “Courtesy of the Red, White & Blue (The Angry American)” (2002)

“As far extreme as I seem, I’m probably catching the average Joe in the middle better than anybody,” Keith told Dan Rather of this red-hot No. 1, which he wrote a week after the attacks on Sept. 11.

Though it took some heat from critics for taking patriotism too far, Keith and his fans disagreed and the outspoken singer had zero regrets. “The higher you fly, the bigger targets you make. And I can take that. And I’ll be there every time,” he said. “If they need me to respond, I’ll be that guy because I’m not gonna lay down. And I’m not gonna shut up.”

12. “God Love Her” (2008)

“She holds tight to me and the Bible on the back seat of my motorcycle / Left her daddy standin’ there, preachin’ to the choir, you see / God love her. Oh, me and God love her,” Keith sings on this No. 1 hit about a rebellious young woman in love with a bad boy. “This is one of my favorite songs that I’ve ever written,” Keith stated of this No. 1 hit he says just poured out like wildfire when he collaborated on it with Vicky McGehee.

11. “As Good As I Once Was” (2005)

Enjoy a beer with this humorous ode to feeling one’s age — “I ain’t as good as I once was, but I’m as good once, as I ever was” — which spent six weeks at the No. 1 position on Billboard’s Hot Country Songs chart. Its equally amusing video finds Keith taking everything from Viagra (for a potential romantic interlude with twins) to a nose-destroying punch in the face after his failed attempt at joining in on a bar fight. It’s all wildly entertaining, and the clip won him a CMA Award for Video of the Year.

10. “You Shouldn’t Kiss Me Like This” (2000)

Even though the country cutup threw a gag in at the end of this otherwise sultry video, the song itself is pure will-they/won’t-they romantic tension, which shows off a softer side of the artist. “You shouldn’t kiss me like this, unless you mean it like that / ’Cause I’ll just close my eyes and I won’t know where I’m at / We’ll get lost on this dance floor, spinning around, and around and around, and around,” Keith sings, as listeners get as breathlessly caught up in the moment as he is.

9. “Made in America” (2011)

As one line notes, “Every day’s Independence Day” thanks to this perfectly patriotic tune in Keith’s country-strong catalog, which includes a nod to his father who was a Marine veteran. “I liked the message [and] getting to put…WD-40 and all the American stuff in there,” the artist said of the tune he co-wrote with Bobby Pinson and Scott Reeves, adding, “And you get to talk about your old man,” he added of a touching bonus, “so it made sense to do it, and it’s been a crowd-favorite.”

8. “Beer for My Horses” (2002) Toby Keith songs

“It’s so Old West that I [wanted] Willie Nelson to sing part of it,” the artist told Dan Rather of this song, which he took directly to the legendary outlaw artist himself. When he shared the line leading up to the title — “it’s whisky for my men, beer for my horses” — Nelson said, “I don’t even need to hear it: I’m in!’ And it’s a six-week No. 1,” Keith shared.

The duo teamed up in 2008 for a film based on the song, though the film was a misfire. “There’s a lot of reasons for people to hate on that movie, but it’s hilarious,” Keith said, sticking to his guns. “The movie’s funny…It was a complete joy [to make].”

RELATED: Willie Nelson Songs: 15 of the Outlaw Country Icon’s Hits, Ranked & the Stories Behind Them

7. “American Soldier” (2003) Toby Keith songs

There’s a gentle power, as Billboard noted, about this poignant tribute tune for the proud and selfless servicemen and women of this country. “We get so desensitized seeing them on the news every night that we forget that under the helmets is a mind, under the camouflage is a heart,” Keith told the Baltimore Sun of his No. 1 hit, which he wrote while tapping into the powerful memories he made on his frequent USO tours visiting the troops overseas.

RELATED: 15 Country Songs that Honor Veterans and Say “Thank You For Your Service”

6. “My List” (2001) Toby Keith songs

Keith, who’d dabbled in acting and films, as noted above, guest-starred on an episode of Touched By An Angel to perform this heartfelt song inspired by Sept. 11’s tragic events. Wide Open Country calls it “a tender tribute to the New York City firefighters who put it all on the line that fateful day.”

The list mentioned in the title refers to the things in life that truly matter, yet often get lost in the shuffle of everyone’s busy lives: “Raise a little hell, laugh ’til it hurts, put an extra five in the plate at church / Call up my folks just to chat, it’s time that I make time for that,” Keith sings, adding, “Just start livin’, that’s the next thing on my list.” The message clearly resonated with fans, as the quiet yet impactful tune spent five weeks at No. 1.

5. “I Wanna Talk About Me” (2001) Toby Keith songs

Though it may be a bit of a lighthearted offering from Keith, this sure is a fun one to sing along to. “I wanna talk about me, wanna talk about I / wanna talk about number one, oh my, me my / what I think, what I like, what I know, what I want, what I see,” the singer spits out in an addictive, rapid-fire country tongue-twister of Toby Keith songs about a guy fighting for equal airtime with his girlfriend.

Written by Bobby Braddock and intended for Blake Shelton, the song landed perfectly with Keith, who wound up a big winner after nabbing it since he had everyone talking about, well, him, and the song’s colorful, playful video.

4. “Red Solo Cup” (2011) Toby Keith songs

In certain circles, this song was inescapable, and whether you loved it or hated it, you would find yourself singing along whether you were drinking from the titular drinking vessel or not. The singer explained the ins and outs of the cup’s powers to Southern Living, and even revealed his go-to drink from it (Jack and Coke). In light of Keith’s passing, look for a sea of red Solo cups to be raised in his honor, which we’re sure the artist would surely love.

3. “How Do You Like Me Now?!” (1999) Toby Keith songs

Talk about bragging rights! This massive hit reigned supreme in the No. 1 position on the Billboard Hot Country Songs chart for five weeks. The song and video are both pure Toby Keith, as he gets his digs in at a onetime dismissive, uninterested girl who made fun of him back in the day. “How do you like me now? Now that I’m on my way? Do you still think I’m crazy standing here today? I couldn’t make you love me, but I always dreamed about livin’ in your radio / How do you like me now?” he asks, relishing the last laugh as his voice comes booming out of said radio.

“A lot of people become successful after they’ve been told they won’t ever be,” Keith had noted of the song’s appeal, “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.”

2. “I Love This Bar” (2003) Toby Keith songs

Fans ate this song up so much that Keith was able to open up his own chain of I Love This Bar & Grill restaurant locations. Billboard’s review promised that it would “be a beer-joint staple for years to come,” and cheers to that, as fans still joyously belt this one out. And everyone can find their place in this fun, sing-along: “We got winners, we got losers,” Keith croons, listing everything from yuppies and bikers to cowboys and truckers, plus blue-collared boys and rednecks, and beyond. “No cover charge, come as you are,” he sings at the end of the chorus, and we’ve gotta agree: we love this bar. (Who’s got next round?)

1. “Should’ve Been a Cowboy” (1993)

Taking it back to where it all started, this signature debut is undeniably one of the best Toby Keith songs. With its unmistakable 90s country sound and references to Marshall Dillon and Miss Kitty, Gene Autry and Roy Rogers, it wistfully recalls the western and frontier lifestyle celebrated in the sepia-toned video. As a testament to the song’s success and popularity with the artist’s fans, it went on to be named the most-played song of the decade.

“The first time I heard it [on the radio], I was going to…Kentucky, and I was with [then touring partner] Shania Twain in the back of the bus,” Keith recalled at a Nashville event in 2007. “Those are good memories. We left Nashville as a bunch of greenhorns and went up into Kentucky and flipped the radio on. ‘Should’ve Been a Cowboy’ came on and it changed my life.” Thanks to Keith for taking us along for the ride.

Rest in peace, Toby.

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