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We Are Jukebox Winos

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“Jukebox Winos stand out as a local favorite, delivering memorable performances at various reputable venues across town. Their diverse repertoire spans across different genres, offering something for everyone. What makes them truly exceptional is their knack for creating a vibrant atmosphere, making each show a delightful experience. Attending one of their performances not only guarantees great music but also provides an opportunity to explore new hangout spots. If you're in search of an enjoyable evening filled with top-notch live music, catching Jukebox Winos in action is definitely worth it.”

Holly Neal, Owner of Malt & Barrel Brewing Co.

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"Jukebox Winos are a great solid band! They are full of energy and interact with the audience. Everyone has a good time!"

Bear Creek Wine Company & Brewery

Walnut Shade Missouri


"Jukebox Winos went above and beyond to play at our private event! They were easy to work with logistically and (of course) played great music to entertain the entire crowd. My guests were beyond impressed with their talent and ability to connect with everyone. 100% would hire them again!"
Traci & Kevin Hennessey 
Branson Missouri


"I've booked Jukebox Winos in two different venues and they've always put on a rocking good show.  Debbie and Greg are two extremely talented musicians who obviously love playing music and entertaining crowds.  They have a knack for reading an audience as well as performing music appropriate to the venue and occasion."  
Clay Miller 
Outback Steak & Oyster Bar

Branson Missouri


"We're so grateful to be able to have Jukebox Winos as one of our favorite gigs at Pop's Smoke Shack in Kimberling City !!!  They're always so professional and just some of the most kind people you'll ever meet.  They're extremely talented in a large variety of genres & great at interacting with their audiences. We're fortunate to have them at Pop's several times a year!"
Donna & Kelly Bradley 
Pop's Smoke Shack of Kimberling City


"We love having Debbie and Greg out at Seven Arrows Taproom! Amazing duo and a great mix of songs! Anywhere from Fleetwood Mac to Kacy Musgrave, you'll find yourself singing along to the great ones!"
Heather & Tom Sattazahn
Seven Arrows Taproom 
Hollister Missouri 


"We love the Jukebox Winos!  They accommodate our requests and encourage us to sing and dance along with them   Their original music is some of the best we have ever heard.  They are so entertaining and a must see!"

Lajean & Johnny Wild

Branson Missouri


"As a songwriter Debbie Olson has that special talent of turning an idea on its head and saying important things in accessible ways. Like her, Debbie’s lyrics are both playful and deep. She is a natural storyteller, a writer who has clearly lived not in her head but in the real flesh and blood world, and drawn from it timeless truths worth singing."

Christa Wells - Co-Founder @artist.and creative community / indie artist - singer - songwriter - poet - conversationalist

Nashville, Tennessee


"Jukebox Winos is one of the best two piece bands I have ever heard. Debbie and Greg are so talented. 
Great harmonies and they do a lot of oldies."
Steve Marberry
Yellville Music On The Square

Yellville, Arkansas


"Greg and Debbie are an Amazing Authentic Duo!  Feels like I am down home when hear them play and sing!! Check them out you will love them!! Rock On!!!"
Glenn Winch 
New Ulm, Minnesota

"Seeing and listening to Jukebox Winos, excellente! The harmonies, this wasn't your first rodeo. We had plenty of choices while in town but glad and jazzed we caught your wonderful sets. Play on, Jukebox Winos!"
Steve & Anita Tahmahkera
La Mesa, California


"I met Debbie at the very first ArtistAnd songwriting retreat that I co-led with longtime friend and business partner Christa Wells. Over the course of 5 or 6 years Debbie kept showing up and putting the work in.  While she was honing her songwriting chops she was also building a successful small business, Jukebox Winos.  If there was ever a star student or a someone that followed their dream, it’s Debbie.  At forty years young she forged ahead and is living in a thriving creative season.  Her writing is deeply rooted in storytelling.  Sharing her ancestor’s story, the story of the Ozark Mountains she loves so much and a descriptive unveiling of her own journey.  I can’t wait to see where this next season takes her.  I look so forward to Jukebox Winos new record due in 2022."

Nicole Witt Singer-songwriter & Artist And Co-Founder

Nashville, Tennessee


"I have been in the audience, performed alongside and co-written songs with Jukebox Winos! They are talented musicians that put on a great show with songs you want to sing along with! Co-writing with Debbie has been a highlight for me and I'm very proud of the songs we've brought to life together. Don't miss a chance to see and hear them!"
Kristen Budde 
Murfreesboro, Tennessee

"I've had the chance to see Jukebox Winos play at two venues in the Branson area.  The music that Debbie and Greg played was outstanding!  Their combination of sound was equivalent to a full band;  I was blown away.  In between sets, Debbie went around and mingled with the audience, she was very personable.  These two are a great local band right here in the heart of the Ozarks."

- Liesa Giebler

Kimberling City, Missouri

"Jukebox Winos repertoire includes everything from Johnny Cash to Pistol Annie's to Van Halen. They keep the party going and audience engaged with their wit, variety, and mostly their amazing talent! Don't miss them!!"

- Patricia and Johnny Herring

Strong, Arkansas

"We stumbled upon the Jukebox Winos performing while we were on our 25th Anniversary trip to Branson in 2018.  Four years later, we still make a point to see them perform when we can.  This duo naturally compliment each other's  talents that will capture your attention!  Like us, you'll return, not only as fans, but friends."  

- Kim & Penny McClung

Barney, Arkansas

"We love the Jukebox Winos. They're lively, fun and play many of the songs that we know and love. They even give free hugs"

- Bob & Carol Wenc

Hancock Michigan Yoopers

"Jukebox Winos -- Love the name, love the music. We look forward to seeing and hearing them when in town. Hanging with friends/ family.. What more can you ask for?"

- Sandy & Jim Kehrein 

Des Plaines Illinois

"Just after moving to Branson in 2019, Laura and I stumbled upon Jukebox Winos at a local venue. Since then we try to see them whenever possible. We absolutely love the song titles they perform. Debbie and Greg have an amazing way of making us feel at home; and we love to bring family and friends to see their show!"

- Dave & Laura Partridge 

Branson Missouri

"We listened to the Jukebox Winos months ago when we were in Branson, MO.  We requested a song that they did not know and Debbie told me that they would learn it and post it on FB.  True to their word they learned this beautiful song, "The Lucky One" by Alison Krauss,  and posted it for us to enjoy.  They are so talented and down to earth, and we hope to have the chance to see them perform in person again."

- Don & Sandi Dolan

Las Vegas, Nevada

"Debbie and Greg are genuine, salt-of-the-earth people. They are so amazing to work with, not to mention their talent. They are the whole package. I used them for an intimate, high-energy reception and they made the evening amazing. Their liveliness, variety, and crowd interaction set the pace for the whole event. Everyone is still talking about how incredible their performance was 2 months later."

- Jarrica Guzman

Branson Chamber & CVB

"We hired Jukebox Winos to play at our private party event to celebrate our loved ones monumental birthday. To say we were pleased would be an understatement. Jukebox Winos provided exceptional entertainment for our diverse group of music lovers! We will definitely be rebooking their musical entertainment services every chance we get! Great people, playing great tunes! We highly recommend booking Jukebox Winos at your next event!"
Michelle Huddleston & Pam Jones
Jane Missouri 


"We love Jukebox Winos! We have been following them for a few years but now that we live in Branson we get to see them weekly. They play a great mix of music and are so enjoyable. Debbie has written some great lyrics that she and Greg have put to music. I often wake up with one of those tunes playing in my head.  🎶 If you get a chance to see them it will be a fun time. They really do  try to please all audiences.  ❤️  "
Barbara & Rick Redford 
Branson Missouri


Jukebox Winos make great music. They play some familiar songs along with some of their own wonderful compositions.
Robert Turner
Montgomeryshire, mid-Wales

"Thanks you two for playing at our private party Saturday! Everyone commented on how you "Kicked it up a notch". We wish you both much continued success sharing your talent and giving joy to others! We will be looking forward to seeing you in the future! "


Steven & Laurie Strouse

Ozark Missouri

"Greg and Debbie are super talents, great voices, and incredible instrumentalists." 

Dennis Denrow


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