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Inside Stephen Colbert’s Unexpected Friendship With Toby Keith and His Genuine Love for Country Music
Say what you want about Stephen Colbert… but he always did what he could to shine a light on country music.
The host of the iconic Late Show is wrapping up his run on May 21. This is after CBS decided to cancel the show last summer, and the most shocking part about it all is that the network isn’t just firing Colbert to bring in a replacement… they’re axing the show altogether.
Here was the network’s statement on the matter:
“We consider Stephen Colbert irreplaceable and will retire ‘The Late Show’ franchise in May of 2026. We are proud that Stephen called CBS home. He and the broadcast will be remembered in the pantheon of greats that graced late night television. This is purely a financial decision against a challenging backdrop in late night. It is not related in any way to the show’s performance, content or other matters happening at Paramount.”
And just like that, we’re already in May of 2026.
Obviously, Colbert has pushed away some viewers during his time as The Late Show host because of the way he leaned into politics. One could make an argument that, coming from his previous home at The Colbert Report, he just continued doing what he did best. But not everyone wanted to drift off to sleep to political finger wagging.
Even so, canceling The Late Show with Stephen Colbert altogether was jarring… especially when you look at late night show ratings. It’s no secret that programs like The Tonight Show and Jimmy Kimmel Live! aren’t the juggernauts that they used to be. Cable television used to be the end goal… now it’s falling behind, and struggling to keep up with modern media.
Despite that turn in how modern day consumers view television, Colbert was still outpacing his late night competitors, and it wasn’t particularly close. Just in 2026, The Late Show with Stephen Colbert averaged 2.70 million viewers per night, while Jimmy Kimmel Live! posted 2.53 million nightly viewers, and The Tonight Show Starring Jimmy Fallon had around 1.33 million.
Essentially, the number one show in late night is going off the air. That being said, the show was reportedly losing the network about $40 million per year.
While some will celebrate that, it’s important to note that Stephen Colbert’s Late Show – and David Letterman’s Late Show before that – was always a late night program that prided itself in putting country music on a pedestal. The likes of John Prine, Willie Nelson, Tim McGraw, Lainey Wilson, Billy Strings, and Kacey Musgraves all appeared on the show over the years. Artists that frequented the show were Chris Stapleton, Sturgill Simpson and Toby Keith.
Colbert just recently had Stapleton on as one of his last musical guests, and as for the other two names I just mentioned… the host of The Late Show is lucky to call himself friends of Sturgill Simpson and Toby Keith.
Stephen Colbert and Toby Keith became friends after the country music legend joined The Colbert Report as a guest in the 2000s. The late show host originally wanted to poke fun at some the Big Dog Daddy’s patriotic songs, but he couldn’t get himself to do it.
Toby was too nice of a guy, and the pair hit it off, and enjoyed each other’s company whenever they crossed paths from then on. In 2015, the country singer played as a part of The Late Show‘s Christmas show, and he gifted Colbert a guitar. Colbert was even the one to induct Toby Keith into the Songwriter’s Hall of Fame.
Here’s a clip from a portion of The Late Show where Colbert eulogized his friend:
Stephen Colbert Says Goodbye To Toby Keith
And that isn’t the only country music friendship that Stephen Colbert boasts.
One of the only late shows that the great Sturgill Simpson would join (especially once Conan was off air) was The Late Show. Colbert strongly considered Simpson (who is also known as Johnny Blue Skies now) as a friend of the show, and the pair apparently bonded over their shared music taste, and great appreciation for John Prine.
The most memorable moments of Simpson and Colbert’s onscreen friendship was when the two would get together and write some sort of zany song. More recently, Sturgill and Simpson wrote an anthem for the Space Force branch of the military. Most famously, the comedian and the country star came together to write a song about Waffle House called “No Shirt, No Shoes, No Knuckleheads.”
Stephen Colbert & Sturgill Simpson Write A Waffle House Hit
The post Inside Stephen Colbert’s Unexpected Friendship With Toby Keith and His Genuine Love for Country Music first appeared on Whiskey Riff.
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