Country artist and entertainer Chuck Wicks stops by the Try That In A Small Town podcast for a wild, honest, and surprisingly emotional ride.

Chuck opens up about his journey from small-town farm kid and college baseball player to Nashville recording artist, radio host, entrepreneur, and autism dad. He shares the real story behind Stealing Cinderella, what it was like to be turned down by RCA the first time, and how he fought his way back to a record deal.

Chuck also talks candidly about raising his nonverbal autistic son Tucker, early intervention, therapies, and the emotional roller coaster of getting an autism diagnosis at Vanderbilt. He explains how that journey has changed his priorities and why he and his wife Cassie (Jason Aldean’s sister) feel called to help other parents find resources.

From there, the guys dive into:

- Chuck’s relationship with Jason Aldean and what Jason is really like offstage

- How Melorosa Wine was born from Cassie’s Cuban family story

- Building Shiners, a wild Cirque-style, adults-only residency show in downtown Nashville

- The stress of chasing country radio, the power of authenticity, and artists taking shots at radio

- The infamous “DipShidiot” segment: road rage, gas station etiquette, youth sports parents, and more

Chuck also teases his upcoming movie on Great American Family Network and Amazon Prime, where he sings multiple songs and steps deeper into acting.

If you love real Nashville stories, songwriting, small-town values, and unfiltered conversations about parenting, business, and faith, this episode delivers.

Subscribe and share if you enjoy the show, and check out the member-only bonus segment for extra songs and stories.

3:06 Early mornings, syndicated radio, and sleep routines

5:05 Family trip out West: Jackson Hole, Yellowstone, elk and bison

7:48 Buffalo vs bison and bear talk

10:00 Hunting, backlash on social media, and eating what you kill

13:44 Health, wild game, and clean eating

14:17 Chuck on being 47, staying in shape, and raising his autistic son

15:12 Tucker’s autism journey: early signs, testing at Vanderbilt, and therapies

18:49 Nonverbal progress, speech breakthroughs, and hope

19:37 Faith, calling, and why parenting Tucker matters more than career

20:00 Connecting with other autism parents (Joe Don Rooney story)

22:19 Treatments, Lucavorin, red light therapy, and access to resources

24:50 “We wouldn’t trade him for anything” – embracing Tucker’s journey

26:17 Belt obsessions, airplane routines, and sensory quirks

26:28 Chuck’s early life: small-town farm kid and college baseball player

28:46 Discovering his voice in college, almost joining a pop group

31:45 First trip to Nashville, meeting RCA’s Jim Catino and singing a cappella

33:56 Development deal, not getting picked up, and starting over

36:18 Four years of grinding, learning to write, and finding his sound

42:40 Second chance: Clint Higham, Chesney camp, and full RCA deal

45:47 Writing Stealing Cinderella from a personal love story

50:00 Singing Stealing Cinderella at Coach Fulmer’s daughter’s wedding

51:37 Realizing the power of a song to move strangers

52:57 The stress of chasing radio hits and perspective with time

53:18 Other cuts and hits, including Jason Aldean’s Don’t You Wanna Stay (context: Aldean cut with Thrash)

56:03 How Chuck met Cassie, realized she was Jason Aldean’s sister, and dating into the Aldean family

1:00:13 The day after: Jason Aldean’s “blessing” phone call

1:02:30 Why Cassie’s three kids changed how Chuck approached relationships

1:03:58 Blended family life: ages of the kids and how fast time moves

1:05:25 What Jason Aldean is really like offstage: loyalty, mystery, and staying the same guy

1:06:29 Jason’s laugh, tight inner circle, and “it could all go away” mindset

1:08:01 Melorosa Wine: starting a wine company with Jason Aldean

1:09:00 Where to find Mellorosa (online, Kroger, ABC, Princess Cruises, Dubai)

1:09:33 The Cuban family story behind the name and “toast to freedom”

1:10:59 Shiners: Cirque-level, adults-only, comedy show in the historic Woolworth building

1:13:35 Writing Shiners during Covid and building a Nashville residency

1:16:10 The history and civil rights importance of the Woolworth building

1:20:20 What to expect at Shiners: moonshiners, aerial acts, crowd work, and “if you’re easily offended…”

1:22:02 DipShidiot segment: explaining the bit

1:22:33 Gas station chaos: Bucky’s pump hogs and parking-lot etiquette

1:25:29 Red velvet “Whitey” vs “Witty’s” custard mix-up

1:27:31 Red Clay Strays controversy: “radio is dead” comment and why radio still matters

1:30:39 Burning bridges you haven’t crossed yet and respecting country radio

1:35:05 Youth sports parents losing their minds vs just being a dad

1:38:01 CMT Awards “edit the chorus” story and learning to be grateful

1:41:03 Road rage story: 75 in a 70 and killing them with kindness

1:43:45 Locker room etiquette: naked close talkers and lifetime fitness stories

1:45:44 Manscaping, gym talk, and ridiculous visual bits

1:46:00 Chuck’s upcoming movie: Great American Family Network & Amazon Prime

1:47:04 Coloring hair, beard guard settings, and aging on camera

1:50:02 Closing: Melorosa Wine, Shiners, Chuck’s music, coffee collab, and podcast wrap

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