Best Upcoming Comedy Shows and Concerts at Casinos Near Dallas | Dallas Observer
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12 Best Casino Shows This Winter

If you love the constant humming of slot machines, the sweet smell of smoke and a chance to risk it all, these casinos are a great destination for your next comedy show or concert.
The Sandman is coming to a casino near you.
The Sandman is coming to a casino near you. Tommaso Boddi/Getty
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Country music and comedy shows are a common theme throughout this winter’s star-studded entertainment lineup at both WinStar (Thackerville) and Choctaw (Durant) casinos in neighboring Oklahoma. Of course, if cowboy boots and belly laughs aren’t your thing, there are still plenty of rock, rap and R&B acts worth crossing state lines for. And if any these performances suck, you can always try to win your money back at the slots.

We have found 12 excuses to skip town this winter and get your live music fix before outdoor venues open back up this spring. Play your cards right and you might win enough that these tickets pay for themselves. Besides, who doesn’t love a reason to roll the dice? Here are the best casino shows taking place close-ish to Dallas this winter.

Dec. 8: Nelly

Choctaw Grand Theater
Buckle up, ask Siri to play “Ride Wit Me” and take a trip back to the early 2000s when this Midwest rapper’s music dominated the airwaves. A night with Nelly is sure to have you feeling nostalgic, so put on your best Y2K get-up (think trucker hats, oversized white tees and Timberlands) and enjoy classics such as “Dilemma,” “Country Grammar” and “Grillz” from this hip-hop legend. Tickets start at $169.


Dec. 8: Adam Sandler

WinStar World Casino
Hands down one of the most iconic comedians of our generation, Adam Sandler will be cracking jokes for the crowd at this 16-and-up event. His standup is undoubtedly just as hilarious as his onscreen performances, so give the gift of Sandler this holiday season because, who knows, he might even play the “The Chanukah Song.” Tickets start at around $125.

Dec. 9: Ryan Bingham & the Texas Gentlemen With Charley Crockett

WinStar World Casino
Dallas artists Ryan Bingham is far from being the biggest name to take the stage at WinStar, but definitely worth seeing this winter, especially with special guests Texas Gentlemen and Charley Crockett. If folk/country meets soft rock is your thing, catch a live jam session from this bull rider turned award-winning, genre-bending artist. Trust us, his moody sound will make the perfect soundtrack to your winter blues. Tickets start at $50.

Dec. 15: Kevin Hart & Friends

WinStar World Casino
As if a comedy show starring Hart could get any better, imagine adding Chelsea Handler and Tiffany Haddish to the mix. The 18-and-up event will consist of two shows on the same night, so there are plenty of tickets — and laughs — to go around. We can't think of a better way to spend a Friday night than with these three top-notch comedians. Name a better trio, we’ll wait. Tickets start at $125.

Dec. 28: Lynyrd Skynyrd

WinStar World Casino
Rock out with this classic all-American band as they celebrate 50 years since the release of their debut album. These Hall of Famers are sure to play all your favorites including “Sweet Home Alabama” and “Free Bird.” Don’t sleep on this show. Tickets start at $70.

Dec. 29: Weezer

Choctaw Grand Theater
If you missed your chance to see Weezer at the peak of their fame, now is the time to cross it off your bucket list. Cancel any competing plans because true Weezer fans will all be belting “Island in the Sun” and “Say it Ain’t So” with or without you. Tickets start around $169.

Dec. 31: Blake Shelton

WinStar World Casino
End 2023 on a high note with one of the biggest names in country music. Oklahoma native Blake Shelton will take the WinStar stage on New Year's Eve, and our fingers are crossed in hopes that his bombshell wife and The Voice co-host, Gwen Stefani, will also be in attendance. Tickets start at around $125.

Jan. 13: Boyz II Men

WinStar World Casino
When you think of slow, sensual '90s R&B, especially the baby-making subgenre, no other than Boyz II Men should come to mind. Think “I’ll Make Love To You” and “End of the Road.” Enjoy a night of fun, heartfelt ballads that will take you back to a time when life was simple and the world still made sense. Tickets start at $45.

Jan 20: John Mulaney

WinStar World Casino
We know, you either love or hate John Mulaney. But if you think the former Saturday Night Live writer and stand-up comedian is funny in his Comedy Central specials, imagine how hard you will cackle seeing him live. Already watched and re-watched all his bits on YouTube? Snag some seats and ugly-laugh until you cry when you hear his newest material. Tickets start at $85.

Jan 27: Brad Paisley

WinStar World Casino
Another household name stops by WinStar in early 2024, and we know country music lovers from all over will be trekking to Oklahoma for a chance to see the Grammy-winning star up close. This show is sure to be fun for everyone from die-hard Paisley fans to the country-music curious crowd. Tickets start at $100.


Feb. 3: Tim McGraw

WinStar World Casino
Whether or not you agree that his onscreen role in Country Strong was McGraw’s biggest accomplishment, there is no arguing that the 56-year-old is one of the greats. Plan a date night, go alone, take your mom — who cares? Even if it costs a pretty penny, this show is something you have to experience once in your life. In the wise words of McGraw himself, “Live like you were dying.” Tickets start at $250.

Feb. 8: Rod Stewart

WinStar World Casino
Believe it or not, the shaggy-haired, raspy-voiced British icon is still rocking stages. And you can bet (get it?) he'll perform hits such as "Maggie May," and "Da Ya Think I'm Sexy?" Look, he did also have that hit "Forever Young," and perhaps we should listen more intently to those lyrics to understand where exactly lies Stewart's fountain of youth. Tickets start at $75.
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