Toby Keith’s songs are some of the most popular songs in country music for the last few decades. 

While the country star has built much of his success on the strength of his rugged, blue-collar drinking anthems, the Oklahoma native is also capable of a broader range of material. He uses his sense of humor to write and record some very unique and even funny novelty songs. He has even demonstrated his softer side in a select handful of well-crafted ballads that could sweep every woman out of her feet.

Check out these nine Toby Keith Songs drawn on all of the different facets of his career.

9. Beer for My Horses

From: Unleashed (2002)

“Beer for My Horses” is a song written by Toby Keith with songwriter Scotty Emerick and recorded with fellow country music icon, Willie Nelson. The song, which sings about a group of men who are talking about catching criminals many generations ago, including an apparent description of murdering, received mixed reviews from music critics.

Still, it peaked at No. 1 for six weeks in the U.S. Billboard Hot Country Songs.

8. Red Solo Cup

From: Clancy’s Tavern (2011)

This is one of the only songs Toby Keith didn’t write within his illustrious career. But what’s interesting is that this tune was never intended to be pitched to anyone to record, Keith only heard the song after someone who worked for him played it. 

He called it “the stupidest song I ever heard in my life.” He also admits that he wasn’t sure about releasing the humorous song, but as he started to play it for people, he noticed them singing along almost immediately.

“‘Red Solo Cup’ is like a squirrel loose in a church house. We can play it in an office and then play five other songs, give it an hour, walk out, and you’d hear the receptionist singing it,” he said. “It’s like nursery rhyme stupid.” 

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

From: Unleashed (2002)

The song was inspired by Toby Keith’s father’s death in March 2001, who was killed in a car accident, as well as the September 11, 2001 attacks on the United States later that year. The song sings about his father’s patriotism and faith in the U.S.A. 

6. American Soldier

From: Shock’n Y’all (2003)

“American Soldier” is about an American in the Army Reserves. According to Toby Keith, the song was written “for all the times that I get to meet the troops on these U.S.O. tours, and since Courtesy of Red, White, and Blue, the P.O.W.s and the families that have come and brought me back my old CD covers and stuff that they had and shown how much support they had (for me), this is my support for the American fighting men and women.”

5. I Love This Bar

From: Shock’n Y’all (2003)

Toby Keith earned another No. 1 single with “I Love This Bar,” and stayed at the top of the charts for five weeks.

Written by Keith and Scotty Emerick, the song describes the frequenters of a local bar, who include “winners, losers, chain smokers and boozers.” It also came with a music video shot at a bar in Chatsworth, California, called the Cowboy Palace Saloon.

4. I Wanna Talk About Me

From: Pull My Chain (2001)

This song stirred up a bit of controversy in 2001 because country fans would call it a rap song and rap fans would call it a country song. Blake Shelton originally cut the record, but he didn’t release it because his label felt a country-rap would be too risky for a newcomer. 

Keith jokingly said 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. 

3. Who’s That Man

From: Boomtown (1994)

“Who’s That Man” is another No. 1 hit by Toby Keith. Here, Keith sings about returning to the home in which he used to live. His ex-wife, children, and their family dog still live in this home, but the wife’s new husband has now taken his place. Now, if that won’t break your heart, what will?

2. My List

From: Pull My Chain (2001)

Not all songwriters can turn a “to-do” list into a hit, but songwriters Rand Bishop and Tim James did just that. “My List” is a song about a man who has a list of things to do every day. He does what needs to be done every day, putting off what he really would like to do — spending time with his family. Eventually, he changed his mind and decided to put his family first, singing “Start livin’, that’s the next thing on my list.”

When Toby Keith heard the demo, he knew it would be a hit, “but it wasn’t consistent with his rebellious, fun-loving, masculine image, and he wasn’t sure his vocal style would work on it. James Stroud, his producer, thought he should give it a go,” Bishop said. The song soared to No. 1 and was on the charts for about 40 weeks, ending 2002 as the most-played song that year in country radio.

1. How Do You Like Me Now?!

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

Whether you admit it or not, there has always been something or someone in our past that we have secretly dreamt of proving about our lives. It could be a former career, a former mentor, or a lover.

Toby Keith did that through “How Do You Like Me Now?!” twenty years ago when the song soared to the top of the charts. It was the country star’s response to people who said that he would never make it in the music business.

“A lot of people become successful after they’ve been told they won’t ever be,” Keith said about the inspiration for the song, which he wrote with Chuck Cannon. “So people can relate to this.”

“How Do You Like Me Now?!” stayed at No. 1 for five weeks and was the No. 1 song on Billboard’s year-end Country Songs chart for 2000. The album of the same name also earned Keith two A.C.M. Awards; he received Album of the Year as both artist and producer.