Toby Keith Passes Away At Age 63

As we mourn and process the loss of one of country music’s biggest (and maybe most misunderstood) icons, we share a look at the — at times — tumultuous first decade of Toby Keith’s recording career.

In the world of entertainment, being different from everyone else is a blessing and a curse. The blessing comes from being different enough to stand apart from a crowd of people trying to do the same thing as you want to do while the curse is also the same thing. And this is how Toby Keith became known as TOBY KEITH, superstar. He was different. He was unafraid to stand out and stand by the courage of his convictions, in fact, he never wavered from them, even if others didn’t truly understand them. He was also, as so many songwriting poets are, inherently introspective. Toby was publicly larger than life but in his own life, he was always reflecting on his life, his family, friends, and American life in the United States and other places around the world.

While Toby Keith was friends with many, he kept a tighter inner circle and was always skeptical of music industry machinations in Nashville. And, who wouldn’t be skeptical when your record label contract (which he earned in nearly a decade of touring with his Easy Money Band in the Southwest) kept being passed around from record label to record label, often touted (as he was for Polydor Nashville, A&M Nashville and DreamWorks Nashville). In fact, Toby recorded five non-holiday albums from 1993 to 1999 for four different labels with Mercury Nashville — who signed him — having released his first one (1993’s Toby Keith) and his fourth (1997’s Dream Walkin’). As the “star” of the independently ran but PolyGram owned labels Polydor Nashville and A&M Nashville, Toby Released his stellar second (1994’s Boomtown) and third (1996’s Blue Moon), respectively.

By the time Toby Keith came to write and record 1999’s How Do You Like Me Now, he was in a full on battle with the executives at Mercury Nashville. The executives who had not signed him and didn’t really like what he was releasing, or wanting to release. Instead of releasing “How Do You Like Me Now,” the label cobbled together the 1998 best-of collection Greatest Hits, Volume One pulled two new tracks from the completed How Do You Like Me Now album, “Getcha Some” and “If A Man Answers,” and, after recording two more tracks the label rejected, that proved to be the final straw as Toby bet on himself, bought the rights to the record and joined his producer James Stroud over at DreamWorks Nashville (the then-new record label in Nashville owned by the DreamWorks company founded by entertainment heavyweights Steven Spielberg, Jeffrey Katzenberg and David Geffen).

That label would be the first time Toby would record consecutive albums for the same record label. Let THAT bit of news sink in for a moment.

In the six years he was with DreamWorks Nashville (1999 - 2005), Toby recorded five albums. All of them, like every one of his non-holiday albums, Platinum or Multi-Platinum. The title track to his first DreamWorks Nashville album, “How Do You Like Me Now,” was an instant multi-week chart-topping smash and it turned the reliable radio star into a superstar. Even with a label that was fully behind him, Toby still had to deal with record label decisions that weren’t following HIS instincts as “When Love Fades” was the album’s first single and it, well, faded into obscurity pretty quickly as the title track was the song Toby believed in the most and, despite being brash. It was really about him and his life, always second-guessed by Nashville and others who said he could never be the who he was then and, for sure, what he subsequently became. The song, despite its personal nature to himself, became an anthem for whatever anyone who heard it needed it to be for their own lives, something the best songs have always been able to achieve.

Albums recorded during this period include the blockbusters Pull My Chain (2001), Unleashed (2002), Shock’N Y’all (2003) and 2005’s Honky Tonk University. The label also released Greatest Hits 2 in 2004 (It also didn’t’ feature any of the hits from Shock’n Y’all).

Despite being propped-up by it’s superstar in Toby Keith, DreamWorks Nashville was overall failing to impress parent company UMG (who bought out the label principals in 2003) by 2005 and the label was folded into UMG Nashville’s MCA and Mercury labels and that left Toby Keith once-again betting on himself as he launched his own label with his trusted manager TK Kimbrell. Show Dog Nashville would be Toby’s final recording home, a label he owned for the remainder of his career and life.

There were all sorts of great songs throughout this time period of his career (1993-2005) from the classic debut single “Should’ve Been A Cowboy” to “As Good As I Once Was” and “Big Blue Note” the final two hits from his DreamWorks era in 2005. In subsequent years with Show Dog Records, Toby recorded and released 10 full studio albums, a double disc collection of holiday standards, released 35 Greatest Hits in 2008 (it compiled hits from his entire career to that point), The Bus Songs (compiling fun, “non-commercial” songs that he’d added as bonus tracks to several albums) and Greatest Hits: The Show Dog Years. The final album released in Toby Keith’s lifetime was Peso In My Pocket with the final single of his lifetime, “Don’t Let The Old Man In” re-issued after his stunning performance at the People’s Choice Country Music Awards show in December 2023.

Toby Keith passed away due to complications from stomach cancer on February 5, 2024 at the age of 62. In the coming days we will bring a retrospective covering the best-known and some of our favorite singles and songs from Toby’s considerable discography of 21 studio albums 42 Top 10 hits and 20 #1 hits.