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.

Lauren has never been afraid of being vulnerable with her fans. Continue reading…

There’s a song off Luke Grimes‘ latest album that he says isn’t meant to be performed in front of people. We’re all familiar with the power that music has to evoke emotions. A certain song can take you back to a specific time in your life. A melody can act as a reminder of a lost loved one. And for Luke Grimes, there’s certain tracks that are meant to be put out into the world… but never played again. The Marshals actor released his sophomore album, Red Bird, back in April, and he described it as a very cathartic and deeply personal project. When he talked more about it in his recent interview with Rolling Stone’s Nashville Now podcast, he said the record as a whole was an effort to be more vulnerable with his music: “It’s definitely a more vulnerable approach to try and put something beautiful into the world. Especially when I think people were probably expect me to do something a little more masculine. There’s sort of like these flavors that you are supposed to put into your music if you are a certain type of person. We were just like, ‘Let’s not do any of that.'” Grimes credited Grammy-winner Dave Cobb, who produced the record, for inspiring him to change things up, and it was his guidance that pushed Grimes to share something with the country music world that felt more honest. The artist says that came naturally, just because of where he finds himself in his life right now: “I had just had a baby, and have this beautiful family. If they weren’t on this record, it would be false. There’s also a lot of loss on this record. Sometimes within the same song, there’s this beautiful aspect of my life and the loss too within the same line.” The country singer lost his father in August of 2022. He’s previously talked about how that loss acted as motivation to chase his music dream, and in Red Bird, the reflection on that loss comes through in many ways… most notably in the song “A Little More Time.” Grimes says that song in particular was hard to get through in the studio, and he strongly doubts that he’ll ever play it again: “In ‘A Little More Time,’ there’s a line about whenever I see my father in my son, I feel like I’ve got a little bit more time with him. That line is very beautiful, but also sort of heartbreaking. It was hard to spit out, honestly. It was hard to sing. I don’t think I’ll ever sing that song again, because I just… it’s not meant to be performed in front of people. It was meant to be a cathartic moment for myself. That song was hard to get through.” Once Luke Grimes got through it, he felt as though the version that exists on Red Bird is the only one that should. “A Little More Time” was a cathartic release for him, and evidently a one time release at that. You can hear more from Luke Grimes in his interview on Rolling Stone’s Nashville Now podcast, which is hosted by Joseph Hudak: The post Marshals Star, Luke Grimes, Says There’s 1 Song He Won’t Ever Play Again: “Not Meant To Be Performed In Front Of People” first appeared on Whiskey Riff.

The early 2000s were an interesting time for country music, a transition period for the genre. We had officially moved past the neon-soaked, golden era of the ’90s, but we hadn’t quite entered the snap-track, “bro-country” period that would eventually take over (and nearly destroy) the genre a decade later. We were starting to move past CDs and certainly cassette tapes, and into the iPod era, but we were not quite into the streaming era of Spotify and Apple Music. Most country music fans know and love the ’90s, especially if they were around for it during their formidable years like I was. Ask me to name my favorite ’90s country songs and we could be sitting around for hours. But when it comes to the early 2000s Y2K era of country music… it just didn’t seem to have the kind of staying power that the decade before it had. It doesn’t stick in my mind as clearly, even though it was more recent. But the early 2000s was PACKED with great country songs from artists like Joe Nichols, Gary Allan, Craig Morgan and more. Many peak 2000s artists have had long and decorated careers, and some ’90s country artists carried their success into the new millennium. But for others, they were a product of the time… maybe a couple big hits here and there, maybe a few years of radio success… there seem to be a ton of one-hit-wonders from this era too. It’s no secret that the bro-country explosion meant the end for a lot of great country acts, as radio pushed clean production wand emotional storytelling to the side for tailgate parties, tight-fittin’ jeans, and shallow truck songs. So here’s 10 early 2000s country music hits that you definitely loved, but maybe you just forgot about. 1. Jessica Andrews – “Who I Am” (2000) It is almost impossible to overstate how massive this song was when it dropped. Jessica Andrews was just a teenager, but she delivered the ultimate coming-of-age, unapologetic anthem for a whole generation of country fans. It hit No. 1 and stayed there, propelled by its unbelievably catchy chorus and relatable message about just staying true to your roots. It is the perfect, breezy 2000s country-pop crossover. And if you had a grandmother named Rosemary, it was, and still probably is, your all-time country music anthem. 2. Chris Cagle – “What a Beautiful Day” (2001) Before Chris Cagle stepped away from the music industry to live a quiet life, he was an absolute force of nature on country radio. “What a Beautiful Day” is the ultimate, roll-your-windows-down, feel-good anthem. It has this driving, acoustic-rock energy that practically forces you to step on the gas pedal a little harder. It peaked at No. 4 on the charts, but it feels like it should have been a multi-week No. 1. He would follow it up with a couple more Top 5 singles, but a #1 would evade him for the rest of his career. 3. Gary Allan – “Tough Little Boys” (2003) Gary Allan made a career out of being the gritty, gravel-voiced bad boy of West Coast country. But in 2003, he dropped this absolute tearjerker that completely flipped the script. “Tough Little Boys” is a brutally honest, acoustic-driven ballad about how having a kid completely softens even the most hardened men. It went straight to No. 1, making grown men cry in their trucks across the country, yet it rarely gets the throwback radio spins it deserves today. As a father myself here in 2026, I can tell you that it absolutely still holds up. 4. Carolyn Dawn Johnson – “Complicated” (2001) If you were a country fan in 2001, you could not escape this song. Carolyn Dawn Johnson perfectly captured the terrifying, stomach-dropping anxiety of falling in love with someone you shouldn’t. It is a massive, soaring power ballad with a chorus that was built for screaming at the top of your lungs in the shower. It is a crime that this isn’t in regular rotation on throwback radio stations. 5. Trick Pony – “Pour Me” (2000) In the early 2000s, Trick Pony was keeping the rowdy, honky-tonk spirit alive with “Pour Me,” a fast-paced, unapologetic drinking anthem. Comprised of Heidi Newfield, Ira Dean and Keith Burns, Trick Pony released a handful of singles to country radio, but never could take it to the next level. After Newfield left to pursue a solo career in 2006, the band called it quits in 2008. 6. Kellie Coffey – “When You Lie Next to Me” (2001) If you went to a wedding between 2001 and 2004, there is a 99% chance this song was playing. Kellie Coffey delivered a pure, unapologetic power ballad that spent weeks parked in the Top 10. It had that sweeping, cinematic production that defined turn-of-the-millennium country romance. Coffey’s vocals on the bridge are absolutely staggering, making it a definitive track of the era that simply faded from the radio dial. 7. Craig Morgan – “Almost Home” (2002) Long before Craig Morgan was singing about International harvesters and redneck yachts, he delivered one of the most heartbreaking, beautifully written story-songs of the decade. “Almost Home” tells the story of finding an unhoused man freezing behind some garbage cans, only to wake him from a dream where he was back in his childhood bed. If you don’t get a lump in your throat listening to the bridge of this song, you might want to check your pulse. 8. Joe Nichols – “The Impossible” (2002) Joe Nichols burst onto the scene with a baritone voice that sounded like it was teleported straight out of 1982. “The Impossible” was his debut single, and it proved that traditional, stripped-down country music could still dominate the charts in the 21st century. It is a quiet, masterful song about surviving the darkest moments of life, and it established Nichols as one of the best pure vocalists of his generation. 9. Steve Holy – “Good Morning Beautiful” (2001) This song is the definition of catching lightning in a bottle. It spent five weeks at No. 1 on the Billboard country charts and became an inescapable radio staple. It is breezy, romantic, and incredibly simple—just a guy waking up and realizing he is the luckiest man on earth. While Steve Holy never quite replicated this massive level of success, he left us with a timeless love song that radio shouldn’t have abandoned. His 2006 hit “Brand New Girlfriend” would be his only other #1 single. 10. Phil Vassar – “Just Another Day in Paradise” (2000) Phil Vassar brought the piano back to the forefront of country music, and this track is his absolute masterpiece. It perfectly captures the chaotic, exhausting, beautiful reality of raising a family and trying to keep your head above water. With lyrics about broken washing machines, screaming kids, and stolen moments in the kitchen, it is the ultimate everyday-man anthem that still holds up flawlessly today. The post 10 Country Songs From the Early 2000s That You Still Love But Probably Forgot About first appeared on Whiskey Riff.