I’ll never get tired of a Toby Keith story. It doesn’t matter where it comes from. As long as we get more insight into the full life that the Big Dog Daddy lived, that’s all that matters. Though we lost the country music legend back in February of 2024, his legacy and his music will forever live on… and the stories that other country music artists will help keep his spirit alive. The latest Toby Keith story that I’ve come across is courtesy of the rodeo cowboy turned country singer Chancey Williams. The authentic, western artist is very talented in his own right, and he caught the eye of Toby Keith at one point, which sparked a friendship. While Williams was on The Jarrod Morris Vibe podcast, he broke into a story about his friendship with Keith led to one very late night in Cheyenne, Wyoming. Chancey was there for the Cheyenne Frontier Days rodeo (it’s a big deal in Wyoming), and he had already played and was done for the night… or so he thought: “We were playing at Cheyenne Frontier Days and had got done, and it was like 2 a.m. and I went back to the hotel room. The hotel phone rings. I pick up the hotel phone, and they’re like, ‘Hey, we’ve got Toby Keith down here.’ I was kind of alcohol-ed up. I had been drinking… I was like, ‘Bulls***, put him on.’ He was like, ‘What are you doing? Get down here, we just flew in.’ Toby was playing the main stage the next day. He was like, ‘Hey let’s go cruise around in the van.’ It was like 3 in the morning in Cheyenne.” When Toby Keith asks you to go cruising, it doesn’t matter what time of day it is… you go. Williams threw back on his boots, headed down to the lobby and met Toby Keith. They ended up loading into the van and driving around (someone else named Jason was driving them). The only problem? They ran out of “cruising beer” at one point, and nowhere in Cheyenne was still serving. Toby had an idea: “We’re driving around Cheyenne. We run out of beer, Toby says, ‘Let’s go get some more.’ They don’t serve beer in Cheyenne after 2, and I had already had enough. Toby said, ‘I know where there’s beer. Jason, go to the airport.’ They go to the private airport, nose the ol’ van up to Toby’s jet. Toby’s got whiskey and (whatever else). We partied.” Imagine hanging out with Toby Keith on his private jet and throwing back beers until the sun comes up. Chancey Williams was quite literally living the dream. And the dream got that much better when Williams jokingly threw out the idea of helping Toby sing “Should’ve Been A Cowboy” during his Cheyenne Frontier Days performance. It was just a joke… but the Big Dog Daddy was all for it: “I threw out there, ‘Hey, if you need help singing ‘Should’ve Been A Cowboy’ tomorrow in Cheyenne, I’ve been practicing it for all these years.’ He was like, ‘Be there tomorrow.’ And I was just kind of joking. He was like, ‘No, be there tomorrow and come up and sing with me.’ 20,000 people at Cheyenne Frontier Days. I woke up in the morning, texted his agent asking, ‘Hey man, was Toby serious?’ (He was like), ‘Yeah, he’s always serious. Just come to the show early and we’ll figure it out.'” View this post on Instagram A post shared by The Jarrod Morris Vibe Podcast (@thejarrodmorrisvibe) Never hurts to ask. Chancey Williams is eternally grateful for the graciousness that Toby Keith extended to him. He’ll never forget sharing the stage with the country music legend, and he insists that there’s no one else like the Big Dog Daddy… and there likely won’t ever be: “There’s stars in country music, and then there’s superstars. Toby was one of the superstars. How many of those superstars let their ‘intern’ come and sing the biggest song of their career? None… so I went out and sang with Toby. It was a memory that I’ll have forever.” You can hear more from Chancey Williams in the interview below: The post Chancey Williams Recalls Late Night Beer Run With Toby Keith That Ended With Them Drinking On His Private Jet first appeared on Whiskey Riff.