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. A two-disc Christmas album, A Classic Christmas, followed later in 2007. In 2008, Keith completed his Biggest and Baddest Tour. On May 6, 2008, he released 35 Biggest Hits, a two-disc compilation featuring most of his singles to date, as well as the new song "She's a Hottie", which peaked at number 13 on Billboard's country songs chart.
Keith released "She Never Cried in Front of Me", which went to number 1 in 2008. Its corresponding album, That Don't Make Me a Bad Guy, followed on October 28, 2008. It was followed by "God Love Her", also a number 1 hit, and "Lost You Anyway". American Ride, in 2009, produced another number 1 in its title track. It was followed by the Top 10 hit "Cryin' for Me (Wayman's Song)", a tribute to basketball player and jazz bassist Wayman Tisdale, a friend of Keith's who died in May 2009.
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. Keith produced the album with session guitarist Kenny Greenberg and recording engineer Mills Logan.
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.
In mid-2013, he entered the charts with "Drinks After Work", the first single from his seventeenth album, also titled Drinks After Work. 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.
