Legends Never Fade as Alabama Delivers Timeless Windsor Show

Alabama Caesars Windsor 2025

More than five decades after three cousins from Fort Payne first picked up their instruments, Alabama proved Thursday night at The Colosseum at Caesars Windsor that legends don’t fade — they simply refine their craft. Randy Owen, 75, and Teddy Gentry, 72, led the Country Music Hall of Fame ensemble through a masterful 90-minute set that balanced their chart-topping catalog with intimate storytelling, delivering both the spectacle and warmth that has defined their remarkable career.

The performance marked another stop on Alabama’s Roll On II tour, their first major touring cycle since the November 2022 death of founding member Jeff Cook. While Cook’s absence was felt, Owen and Gentry have assembled a skilled backing band that honors the group’s signature sound while allowing the duo’s chemistry to remain the evening’s focal point.

Alabama opened with “Tennessee River,” their 1980 breakthrough hit that launched one of country music’s most successful runs. Owen’s distinctive vocals showed remarkable preservation, while Gentry’s bass lines anchored the familiar arrangement. The song choice proved strategic, immediately establishing the evening’s nostalgic atmosphere while showcasing the band’s enduring vocal harmonies.

The energy escalated with “If You’re Gonna Play in Texas (You Gotta Have a Fiddle in the Band),” complete with the fiddle flourishes that made the 1984 single a crossover success. Owen moved across the stage with renewed vigor, his earlier mobility concerns giving way to the entertainer’s instincts that have sustained Alabama through countless performances.

The current lineup features several notable musicians, including Jason Roller on guitar and vocals from Indiana, who also serves as a Grand Ole Opry backing musician when off the road with Alabama. Owen proudly introduced Gordon Mote on keyboards, praising him as “one of the great vocalists that we’ve ever seen” and noting that “Gordon Mote has played on over 100 number one country singles”. The band also includes fiddle player Megan Mullins Owen on fiddle, Alabama’s first female member, who brings both exceptional musicianship and family connection as the wife of Randy Owen’s cousin.

Between songs, Owen shared stories that revealed the band’s journey from bar circuit to superstardom. “Time out for the old team — it’s about two hours past my bedtime,” he told the audience with a chuckle, before launching into tales about songwriter Dave Loggins pitching material in their recording studio. His casual delivery made the 2,500-seat venue feel like a living room conversation.

The evening’s most poignant moment arrived during Owen’s discussion of “Angels Among Us” and his work with St. Jude Children’s Research Hospital. “Thanks to them and people who listen to country radio stations all around the country and Canada and all around the world, really, you have helped raise, since 1989, over $1 billion,” Owen said, his voice carrying genuine emotion. The song that followed carried additional weight, connecting Alabama’s charitable legacy with their musical impact.

Mid-show classics “Song of the South” and “Love in the First Degree” demonstrated why Alabama accumulated 43 number-one singles during their career peak. The audience sang along enthusiastically, with Owen encouraging participation rather than simply performing for passive listeners. “Can’t Keep a Good Man Down” earned particular audience response, with Owen sharing a letter from a fan whose wife regularly tells him “you can’t keep a good old big old boy down”.

Owen’s storytelling reached its peak during discussions of Dave Loggins’ late-night phone calls. “It was about 2:31 in the morning, Dave called me and he said, ‘Hey man, what are you doing?’ I said, ‘Dave, I’m sleeping.’ He said, ‘Man, you know, you’ve been talking to me about a truck driving song'”. This introduction led into “Roll On (Eighteen Wheeler),” one of several Loggins compositions that became Alabama standards.

The setlist continued with crowd favorites including “Orange Blossom Special,” showcasing Mullins Owen’s fiddle prowess, followed by “Five O’Clock 500” and “You’ve Got the Touch”. Owen made special mention of his family, noting “my uncle Barton is 87 years old in South Carolina” and celebrating birthdays — “John Owen is eight years old today and Alison is 10 years old today”.

The main set concluded with a medley of “Dixieland Delight” and “Will The Circle Be Unbroken,” before Alabama returned for an encore performance of “Mountain Music”. Owen and Gentry remained on stage afterward, tossing t-shirts to fans and clearly savoring the connection with their audience. Owen’s closing remarks emphasized the duo’s appreciation: “I never forget that there’s two guys from Lookout Mountain, Alabama that love you and appreciate you and thank you for coming out to watch us play our guitars and sing our songs”.

Despite the inevitable signs of aging, Alabama’s performance demonstrated why they’ve sold over 80 million albums and influenced countless country acts. Owen’s storytelling ability and Gentry’s steady presence created an evening that felt both grand and intimate.

Higgi Caesars 2025

Local opening act Higgi warmed the Windsor crowd with a brief but effective set mixing original material with country favorites. The hometown band demonstrated solid musicianship and served as an appropriate appetizer for the main event, earning genuine applause from the capacity audience before Alabama took the stage to deliver their career-spanning performance that proved legends truly never fade.

All photos by Dan Savoie

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Dan's been rockin' the journalism scene from coast to coast, scribbling for Canadian papers and jamming with iconic mags like Rolling Stone and Metal Hammer. He's racked up chats with a who's-who of rock royalty, from KISS to Metallica. Yeah, he's living the dream, one interview at a time.