Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

Toby Keith Songs Spanning His Illustrious Career In Country Music

Toby Keith Songs
by
  • Arden is a Senior Country Music Journalist for Country Thang Daily, specializing in classic hits and contemporary chart-toppers.
  • Prior to joining Country Thang Daily, Arden wrote for Billboard and People magazine, covering country music legends and emerging artists.
  • Arden holds a Bachelor of Arts in Journalism from the University of Tennessee, with a minor in Music Studies.

Nearly three decades ago, Toby Keith released his debut single. Since then, he has spent his career moving forward with an outlaw swagger and even becoming a household name. Well, it was expected as he came to Nashville with some of the strongest material. Toby Keith songs fit just about every emotion – love, happiness, heartache, loss, and even a little bit of rage – that really struck a chord with its audience.

Play these hits below, and you’ll know what we’re talking about.

1. “Courtesy of the Red, White, and Blue (The Angry American)”

From: Unleashed (2002)

Shortly after the 9/11 terrorist attacks in 2001, Keith wrote “Courtesy of the Red, White, and Blue” that established his unwavering support to the American armed forces. It was inspired by what he thought would have been his father’s thoughts about the terrorist attacks.

2. “How Do You Like Me Now?!”

From: How Do You Like Me Now!? (1999)

When Toby Keith almost didn’t make it into country music – and worse, was told his songs weren’t good enough – he considered giving up. Luckily, he landed a record deal with the now-defunct DreamWorks Nashville label and released “How Do You Like Me Now?!” – a song about a guy wondering if the girl who rejected him in high school still remembers him now that he is famous.

It became one of the biggest hits of his career – it was hailed the No. 1 Country Song of 2000 and was his first major crossover hit, peaking at No. 31 on the Billboard Hot 100.

3. “You Shouldn’t Kiss Me Like This”

From: How Do You Like Me Now!? (1999)

The fourth and final single of How Do You Like Me Now!? The song is about two people falling in love after their first kiss also reached No. 1 on Billboard’s Hot Country Songs chart – where it spent three non-contiguous weeks. It also peaked at No. 32 on the Billboard Hot 100.

4. “I Wanna Talk About Me”

From: Pull My Chain (2001)

Keith is said to have invented country-rap, and “I Wanna Talk About Me” is one proof of that – a rhythmically spoken song about a man’s frustration in his lack of ability to communicate with his partner, who always talks about herself.

5. “Who’s That Man”

From: Boomtown (1994)

Keith was definitely raising a glass to toast to his success when he wrote “Who’s That Man,” a song about a man coming back home to where he used to live. There, he found his wife, children, and even their family dog – but his wife’s new husband has now taken his place. 

6. “Me Too”

From: Blue Moon (1996)

Struggling to say the words “I love you” to your significant other? Keith surely knows how you feel, and he sings about such a dilemma in “Me Too.” The romantic ballad tells the tale of a man who is not so good with words that he instead performs actual tasks as a way to show his affection.

7. “American Soldier”

From: Shock’n Y’all (2003)

After performing about 160 shows over nine years via USO tours, Keith shows support for the American fighting men and women once again in the incredibly moving, patriotic anthem “American Soldier.”

8. “My List”

From: Pull My Chain (2001)

The song finds Keith ticking things off his list of duties and responsibilities but, in the end, decides to start living and make more time for his family. It rings true to the singer as he enjoys spending time with his family, including Toby Keith’s wife Tricia and their three children.

9. “Cryin’ for Me (Wayman’s Song)”

From: American Ride (2009)

Written by Keith himself, the song is dedicated to his friend, jazz musician Wayne Tisdale who died after a two-year battle with cancer.

10. “A Little Less Talk and a Lot More Action”

From: Toby Keith (1993)

Originally recorded by Hank Williams Jr., the song became a big hit of Keith – reaching No. 2 on Billboard’s Hot Country Songs chart.

11. “Whiskey Girl”

From: Shock’n Y’all (2003)

Keith stormed the top of the charts with a song about “the epitome of a redneck girl.” The track also appeared on Keith’s two-disc compilation album in 2008 called 35 Biggest Hits.

12. “I Love This Bar”

From: Shock’n Y’all (2003)

Keith describes a local bar’s patrons – including “winners, losers, chain smokers and boozers” in “I Love This Bar.” It then reached the top of the charts – but more importantly, it set off a new business for the singer: Toby Keith’s I Love This Bar & Grill.

13. “Should’ve Been a Cowboy”

From: Toby Keith (1993)

Toby Keith scored his first No. 1 hit with “Should’ve Been a Cowboy.” It catapulted him into massive country stardom, launching a lengthy and fruitful career.

14. “American Ride”

From: American Ride (2009)

Keith describes “American Ride” as a “song of the times” where the narrator lists off different politically oriented issues in the country – from illegal immigration to rising gasoline prices.

15. “Red Solo Cup”

From: Clancy’s Tavern (2011)

The simple appeal of this party-hearty anthem made its music video go viral upon its release. To date, it spawned more than 60 million views on YouTube.

More Toby Keith’s Songs

Toby Keith has proven over and over again how much of a terrific artist he is. Here are some more of his songs that you need to check out.

  • “She Never Cried in Front of Me”
  • “You Ain’t Much Fun”
  • “Does That Blue Moon Ever Shine on You”
  • “We Were in Love”
  • “I’m So Happy I Can’t Stop Crying” (with Sting)
  • “A Little Too Late”
  • “I’m Just Talkin’ About Tonight”
  • “Who’s Your Daddy?”
  • “As Good as I Once Was”
  • “Beer for My Horses”

How about you? What are your favorite songs of Toby Keith?

Latest Stories

Toby Keith performs with his American flag guitar, the same patriotic spirit that fueled his song "Courtesy of the Red, White, and Blue."

The Untold Truth Behind Toby Keith’s “Courtesy of the Red, White, and Blue (The Angry American)”

When Toby Keith sat down with a fantasy football stat sheet and scribbled out “Courtesy of the Red, White, and Blue”, he didn’t just write a song. He lit a ...

Toby Keith plays guitar with an American flag design, capturing the patriotic vibe perfect for a Fourth of July country playlist.

35 Patriotic Country Songs to Turn Your Backyard Into the Ultimate 4th of July Party

Nothing says freedom like blasting a rowdy country playlist while you torch a few burgers, keep the cooler stocked, and watch your drunk uncle light fireworks way too close to ...

Keith Urban sits next to Nicole Kidman looking serious, a moment that echoes him shutting down talk about her steamy movie scenes.

Keith Urban Shuts Down Interview When Nicole Kidman’s Scenes With Younger Men Are Mentioned

Some lines just ain’t worth crossing, especially when you’re asking Keith Urban about Nicole Kidman and Zac Efron rolling around on screen. This week, the whole thing went sideways when ...

Tim McGraw sits outdoors with Faith Hill, leaning on a cane, sparking questions about his health but showing their strong bond.

Tim McGraw Using a Cane With Faith Hill Beside Him Raises Questions About His Health

Sometimes country music’s strongest cowboys need a little help standing tall, and Tim McGraw’s latest photo has folks asking how much longer he can keep carrying that torch. It’s not ...

Garth Brooks and Trisha Yearwood smile together at an event, standing united amid the ongoing sexual assault lawsuit drama.

Garth Brooks’ Marriage With Trisha Yearwood Reportedly Unshaken by Sexual Assault Lawsuit

Nothing tests a marriage like ugly headlines, but Garth Brooks and Trisha Yearwood are riding out this storm shoulder to shoulder. Since last October, Garth Brooks has been staring down ...

Country legend George Jones plays guitar under spotlight, embodying the raw heartbreak behind these 12 most depressing country songs.

These 12 Depressing Country Songs Will Have You Sobbing and Hitting Repeat All Night

Straight from the depths of Reddit’s country corner, here’s a list built by real fans who know heartbreak better than any Nashville hit machine ever could. These songs weren’t picked ...

Jimmy Swaggart preaching passionately in an undated photo, remembered now after his death at 90 from a heart attack.

Televangelist Jimmy Swaggart Dies at 90 Just Weeks After Suffering a Massive Heart Attack

There’s a hush across Pentecostal churches this week as believers remember Jimmy Swaggart, the firebrand evangelist, gospel singer, and TV preacher who spent decades filling stadiums, living rooms, and airwaves ...

Gavin Adcock onstage raising a whiskey bottle while blasting Beyoncé’s ‘Cowboy Carter’ as “not real country music.”

Viral Country Star Gavin Adcock Slams Beyoncé’s ‘Cowboy Carter’ Says ‘That S— Ain’t Country Music’

Some headlines feel like a parody of the country music circus these days, and this is one of them. Gavin Adcock, the beer-slinging viral star who built half his brand ...

George Strait beams onstage at Patriots Stadium, guitar in hand, as he brings Texas charm with “All My Ex’s Live in Texas.”

George Strait Brings Lone Star Magic to Patriots Stadium With “All My Ex’s Live in Texas”

Some legends don’t need confetti cannons or stadium-shaking pyros. They just need a guitar, a baritone voice, and a song about every ex they ever outran in a pickup truck. ...

Beyoncé points at her Buffalo Soldiers shirt during her Cowboy Carter tour, the shirt that sparked backlash for its wording.

Beyoncé Under Fire for Wearing Shirt That Calls Native Americans “Enemies of Peace”

Some controversy doesn’t fade with the stage lights. Just ask Beyoncé. The Houston-born superstar is facing backlash after wearing a T-shirt during her Cowboy Carter tour in Paris that some ...