Keith went to
Nashville, Tennessee, where he
busked (street performing) along
Music Row to no avail, until producer
Harold Shedd signed him with
Mercury Records after receiving a copy of Keith's demo tape from a flight attendant who was a fan of Keith's. on the U.S.
Billboard Hot Country Songs chart in 1993, and it reached number 93 on the
Billboard Hot 100.
Stephen Thomas Erlewine of
AllMusic wrote of the album, "It is given a production that's a bit too big, clean, glossy and cavernous for Keith's good—it fits the outsized sound of early-'90s radio, but not his outsized talent—but beneath that sheen the songs are very strong." He also thought that it showed the signs of the style that Keith would develop on subsequent albums. The album's success led to Keith touring with then-labelmates
Shania Twain and
John Brannen. peaked at number 2. Following it were "
A Woman's Touch" at number 6, and "
Me Too", which became his third number one hit in March 1997. and the two also performed the song at the 1997
Country Music Association awards. After this song, the album's
title track reached number 5, while "Double Wide Paradise" peaked at number 40. and "If a Man Answers". Both were released as singles, with "Getcha Some" reaching the Top 20, but "If a Man Answers" became his first single to miss the Top 40. After exiting Mercury, Keith co-wrote
Shane Minor's debut single "
Slave to the Habit" with
Chuck Cannon and
Kostas.
1999–2002: How Do You Like Me Now?! and Pull My Chain In 1999, Keith moved to
DreamWorks Records' Nashville division, of which Stroud served as president. His first release for the label was "When Love Fades", which also failed to make Top 40. The album, which was certified platinum, produced a Top 5 hit in "
Country Comes to Town" and another number 1 in "
You Shouldn't Kiss Me Like This". It was also his first album to feature songs co-written by
Scotty Emerick, who would be a frequent collaborator of Keith's for the next several albums. Steve Huey wrote that this album "had a rough, brash attitude that helped give Keith a stronger identity as a performer."
2002–2004: Unleashed and ''Shock'n Y'all'' In 2002, Keith released the
Unleashed album which included four singles. First was "
Courtesy of the Red, White and Blue (The Angry American)", which Keith wrote in 20 minutes as a response to the
September 11, 2001 attacks. The song references Keith's father, a
United States Army veteran who died that March in a car accident. Both this song and "
Who's Your Daddy?" were number 1 hits, with "
Rock You Baby" reaching number 13. The last single was "
Beer for My Horses", a duet with
Willie Nelson which spent six weeks at the top of the country charts. At the time, it was also Keith's highest entry on the Hot 100, at number 22. The album was followed in late 2004 by
Greatest Hits 2, which included three new songs: "
Stays in Mexico", "Go with Her", and a cover of
Inez and Charlie Foxx's "
Mockingbird", recorded as a duet with his daughter,
Krystal Keith. "Stays in Mexico" was a number 3 hit on the country charts, while "Mockingbird" peaked at number 27.
2005–2024: After DreamWorks On August 31, 2005, Keith founded a new label,
Show Dog Nashville. Its first release was his 2006 album
White Trash with Money, followed by the soundtrack to
Broken Bridges. He also abandoned Stroud as co-producer in favor of Cannon's wife,
Lari White. The album included three singles: "
Get Drunk and Be Somebody", "
A Little Too Late", and "
Crash Here Tonight".
Big Dog Daddy followed in 2007, with Keith serving as sole producer. Its singles were "
High Maintenance Woman", "
Love Me If You Can", and "
Get My Drink On". "Love Me If You Can" became Keith's first number 1 hit since "As Good as I Once Was" more than two years prior. as well as the new song "
She's a Hottie", which peaked at number 13 on Billboard's country songs chart.
Bullets in the Gun was released on October 5, 2010. This was Keith's first album not to produce any top 10 singles, with "
Trailerhood" reaching number 19, followed by the
title track and "
Somewhere Else" both at number 12. On October 25, 2011, ''
Clancy's Tavern'' was released. The album included the single "
Made in America", written by Keith along with
Bobby Pinson and
Scott Reeves, which went to number 1. Following it was "
Red Solo Cup", which had previously been made into a music video which became popular. Upon release as a single, "Red Solo Cup" became Keith's best-peaking crossover, reaching number 15 on the Hot 100. The album's final single was "
Beers Ago" at number 6 in 2012. In December 2011, Keith was named "Artist of the Decade" by the American Country Awards. Keith's sixteenth album,
Hope on the Rocks, was released in late 2012. It produced only two singles, both of which are top 20 hits: "
I Like Girls That Drink Beer" reached at number 17 and the
title track peaked at number 18. The album's second single is "Shut Up and Hold On". In October 2014, Keith released "
Drunk Americans", the lead single from his eighteenth studio album,
35 MPH Town. In April 2015, Keith released "
35 MPH Town", the album's title track and second single. In 2015, Keith was also inducted into the Songwriters Hall of Fame. In September 2017, Keith released the compilation album,
The Bus Songs. The album contains twelve songs: two new, five re-recorded, and five previously released songs. The new songs on the album are "Shitty Golfer" and "Wacky Tobaccy". In the U.S.
The Bus Songs topped the
Billboard Comedy Albums chart for 11 weeks. It also reached number 6 on the Top Country Albums chart and 38 on the
Billboard 200 chart. In 2021, Keith featured on the
Brantley Gilbert single "
The Worst Country Song of All Time" with
Hardy. On January 13, 2021, President Trump awarded Keith the
National Medal of Arts. The award was given in a closed ceremony, alongside fellow country musician
Ricky Skaggs. On September 28, 2023, after receiving the first Country Icon Award at the People's Choice Country Awards, Keith performed publicly for the first time since his June 2022 cancer diagnosis announcement. His performance of "
Don't Let the Old Man In", which was previously used in
Clint Eastwood's 2018 film
The Mule, received a standing ovation. Keith's final performance was held in
Las Vegas, Nevada, at the
Park MGM, on December 14, 2023. His last studio recording was included on
Hixtape: Vol. 3: Difftape, a
tribute album to
Joe Diffie, to which Keith joined
Luke Combs on a rendition of Diffie's single "
Ships That Don't Come In". In March 2024, one month after his death, it was announced that Keith would be posthumously inducted into the
Country Music Hall of Fame, having been elected just hours after his death. ==Acting career==