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Remembering Toby Keith’s ‘Red Solo Cup’ and 9 other of his biggest songs

Keith, who died at the age of 62, enjoyed an enduring level of success with songs that ranged from playful to the serious.
/ Source: TODAY

Country music star Toby Keith has died at the age of 62, according to a message on his website. The news comes after Keith announced in June 2022 that he had been diagnosed with stomach cancer.

Keith was a seven-time Grammy nominee who leaves behind a collection of songs that helped make him one of the brightest and most popular artists in country music, spanning a career that took off in 1993 with his debut single, “Should’ve Been a Cowboy.”

That song would set the tone for Keith, who became one of the most recognizable names in country, as well as a vocal patriot, a trait that would surface in his music. He would go on to have 20 No. 1 hits on the Billboard Hot Country Songs chart, while 42 would make it into the Top 10. Here’s a look at some of his most memorable hits.

“Red Solo Cup”

This 2011 song from his album "Clancy's Tavern," about a cup known for being used at parties, turned about to be one of Keith’s signature hits. It’s simple, fun and catchy and while it’s one of his most recognizable songs, this one actually did not top the charts, peaking at No. 9.

"It's an earworm. It's gonna get you," Keith once said about it.

Watch the video for "Red Solo Cup"

Toby Keith performs onstage
Toby Keith performs during the iHeartCountry Festival on Oct. 30, 2021 in Austin, Texas.Erika Goldring / WireImage

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

Keith’s chart-topping 2002 track from his album "Unleashed" was written in response to the Sept. 11 attacks, as well as in the aftermath of his own father's death. It caused a lot of controversy, including a well-known feud with the then-Dixie Chicks, for its lyrical content.

“You can’t go out and support the military in Afghanistan or you get all the right-wing checkmarks that come with it,” he told The Arizona Republic in 2018. “I was like, “Well, I’m just gonna take them. Mark me down. Just check me off however you want to check me off.”

Watch the video for “Courtesy of the Red, White and Blue (The Angry American)”

“As Good As I Once Was”

Along with “Beer for My Horses,” this is the longest running No. 1 hit of Keith’s career, spending six weeks atop the charts in 2005. The song, from Keith's album "Honkytonk University," also earned him a Grammy nomination for best male country vocal performance.

Watch the video for “As Good As I Once Was”

Toby Keith performs
Keith performs at the Country Thunder Music Festival on April 7, 2018 in Florence, Arizona.Rick Diamond / Getty Images

“Beer for My Horses”

This just sounds like a country song, right? Keith teamed up with country music icon Willie Nelson for this track, off of "Unleashed," that rocketed to the top of the charts in 2003. It scored a pair of Grammy nominations, for best country song and best country collaboration with vocals.

The song also inspired the 2008 movie of the same name, which starred Keith, Nelson, Rodney Carrington, Gina Gershon, Ted Nugent and Tom Skerritt.

Watch the video for “Beer for My Horses”

“Should’ve Been a Cowboy”

This was Keith’s debut single from his self-titled debut album and his first No. 1 hit. He told The Arizona Republic in 2018 that he wrote it in 20 minutes, noting how vital the song was for him.

“That was the first one and it’s still the most important one, looking back, because of the great artists I’ve seen come and go that were really talented that never did make it and then they turned around and wrote hits for other people,” he said.

Watch the video for “Should’ve Been a Cowboy”

Toby Keith performs onstage
Keith performs during the 2022 BMI Country Awards on Nov. 8, 2022, in Nashville.Jason Kempin / Getty Images

“How Do You Like Me Now?!”

Keith ushered in the new millennium with this smash, which roared to No. 1 in 2000. The song is from the 1999 album of the same name.

Watch the video for “How Do You Like Me Now?!”

“I Love This Bar”

Another one of Keith’s biggest hits, this track spent five weeks at No. 1 in 2003. The song appears on Keith's album "Shock’n Y’all" and also led to a restaurant chain called Toby Keith’s I Love This Bar & Grill.

Watch the video for “I Love This Bar”

“Made In America”

This song, from "Clancy's Tavern," reflects on goods not made in America and has the distinction of being Keith’s last song to go to No. 1, spending a week atop that charts in 2011.

Watch the video for “Made In America”

“A Little Less Talk And A Lot More Action”

Keith’s career had just kicked into high gear when this song, off his debut album, came out. The song, originally recorded by Hank Williams, Jr., would reach No. 2 on the charts.

Watch the video for “A Little Less Talk And A Lot More Action”

“I Wanna Talk About Me”

Keith hit the jackpot with this uptempo classic from his album "Pull My Chain." It spent five weeks at No. 1 in 2001.

Watch the video for “I Wanna Talk About Me”