One of her earliest supporters. Lainey Wilson is now one of country music’s biggest stars, and many fans now know the story of how she got her start in Nashville, coming from small town Baskin, Louisiana and knowing almost no one in Music City when she first arrived. Lainey did have one important connection, though, an old friend of her grandfather who let her park her camper in his studio parking lot, who also had some connections and worked in the music industry. On the Just Being ERNEST podcast years back, Lainey talked about Jerry and how much he helped her in those early days: “I moved here in August of 2011…There was a guy from my hometown, his name was Jerry Cupit. He had some success in the ’90s with like Ken Mellons, Kevin Sharpe… And crazy story, my daddy’s daddy has always loved music, just wanted to support it any way he could. So in the ’70s he gave Jerry Cupit a few hundred bucks to help him move to Nashville and get started. And as a favor in return, Jerry let me live in his studio parking lot for free for those three years. So he was really my only contact that I knew.” Lainey has spoken before about how hard Jerry’s death was for her to deal with. They were close collaborators, writing over 300 songs together, getting together to write every single day for three years. Jerry wound up getting sick, and ultimately passed away, which Lainey called a very dark time, because they had obviously gotten very close. She shared more about it in her recent Netflix documentary Lainey Wilson: Keepin’ Country Cool, which gives fans an intimate look at her life as she juggles being a country music superstar with everything else she has going on outside of that, including detailing how she got here in the first place. Lainey says Jerry’s passing started a “dark season” of her life, and she felt lost because he was her first and only connection in Nashville, and without him, she really didn’t know what to do. In terms of anyone connected to the industry, he was the first person to really, truly believe in her and he was sure she was going to make it one day. “We realized, oh no, this is not good. That’s when I knew that he’s probably not gonna make it much longer. And he told me, he said, ‘I want you to keep going.’ And then he passed away. I just felt lost and lonely and scared, and it was a very, honestly, like a dark season of my life. I didn’t know which way to go. I didn’t know who to turn to, but I still knew that this was my calling, and I knew that I wasn’t gonna pack it up and go home. I knew that I needed to stick it out and I honestly kind of felt like, I owed it to myself, but I also owe it to him.” She also showed off a binder of old references she’d had different people write for her when she was just starting out, and Jerry’s was absolutely beautiful, and in hindsight, we now know he was right on the money, so to speak: “This is where I got people to write references, so Jerry wrote, ‘Lainey is a complete package. She sings, writes, and will be a superstar. Her talent will demand a place in the ranks of the major country music platform.’ That’s pretty cool. He spoke it.” That he did… most people that make it to Lainey’s level of success in entertainment have someone like Jerry who believes in them just as much, or even more, than they believe in themselves, and that was certainly Jerry for her. And like Lainey mentioned, she knew she was still going to do everything she could to make her dreams become a reality, and that she certainly did. Lainey shared the heartfelt video with the caption: “Jerry helped me find my way in Nashville. I carry a little piece of him with me every time I write.” She never took his help or belief for granted, and he knew she was a super star long before anyone else: View this post on Instagram You can watch the trailer here: The post Lainey Wilson Says She Went Through A Dark Season When Her Mentor Passed Away: “I Felt Lost, Lonely & Scared” first appeared on Whiskey Riff.

He sounds very different than his later work. Continue reading…

I guess it makes sense, since she has a song named after him. If the reports are true, we’re just days away from the massive wedding between pop superstar Taylor Swift and Kansas City Chiefs tight end Travis Kelce. While the couple have remained tight-lipped about their plans, it’s. been reported in recent days that the two would tie the knot at Madison Square Garden on Friday, after it was revealed that permits had been filed for street closures around the venue from July 2-4 and trucks have been spotted unloading massive amounts of gear, with TMZ reporting that the couple would construct a giant castle and garden inside the New York City arena. Earlier this month, the couple were on what many believed to be their bachelor and bachelorette parties. Taylor and her friends reportedly spent the weekend at her house in Rhode Island, complete with fireworks, while Travis and a group including his brother Jason Kelce spent a weekend in California that included a show from EDM producer and DJ Chris Lake and the NASCAR Cup Series race on the street course at Naval Base Coronado. Of course there are many who believe that this whole Madison Square Garden wedding is a decoy, and that the couple really plans to tie the knot at a more intimate ceremony somewhere else. But according to Page Six, it’s really happening and will even feature entertainment from a country music superstar. Tim McGraw is among those who is reportedly set to perform at the massive wedding, along with Fleetwood Mac frontwoman Stevie Knicks. Taylor and Tim have shared the stage multiple times together throughout her career, and Taylor even joined him on the song “Highway Don’t Care” back in 2013 along with Keith Urban. While guests have remained tight-lipped about the wedding plans, rumors began swirling earlier this month that Kenny Chesney had canceled two dates at the Las Vegas Sphere to attend the ceremony. Originally, Chesney’s residency only featured late June dates (his first show back was June 19). However, there was so much demand for those shows that he added more dates in early July… including shows on July 3 and July 4. Because who wouldn’t want to spend the 4th of July hanging out with Kenny Chesney? However, Chesney changed his mind back in April, and according to the Las Vegas Review Journal, he sent out this message to fans who had already bought tickets for those two dates: “Funny thing about holidays, family, and traditions: you don’t realize how important they are until you remember all the things people in your life want to do to celebrate them; the reason people come together, go home and remember, catch up with old friends. Over the last few weeks, I’ve heard about a lot of traditions that wouldn’t be happening – because I was going to play Las Vegas over the 4th of July Weekend. I won’t say I didn’t realize, but I will say: hearing from people I know and care about, I heard them loud and clear. So I’ve made the difficult decision to cancel my shows on July 3 & 4 at Sphere. Not that I don’t want to see you at Sphere, to share this incredible, full-immersion music-visual experience with you. I do.” Back in the day, Kenny was set to take Taylor on a tour with him when she was in the early stages of her career. Though that didn’t work (because the tour was sponsored by a beer brand, and Swift wasn’t 21 at the time), Chesney still chose to help her out financially, and they’ve remained good friends ever since then – which is just one reason fans think he may have scrapped the Sphere dates to attend his friend’s wedding. According to Page Six, the guest list will also include country singers Kelsea Ballerini, Dierks Bentley, and Little Big Town.The post Tim McGraw Reportedly Set To Perform At Taylor Swift’s Wedding To Travis Kelce This Weekend first appeared on Whiskey Riff.

In 2026, country music is Ella Langley's world. Continue reading…