Dustin Lynch and Luke Bryan Team Up For Toby Keith Tribute At Crash My Playa

The pair joined forces to sing “Should’ve Been A Cowboy.” 


Lauren Jo Black

| Posted on

January 23, 2023

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Dustin Lynch, Luke Bryan; Photo Courtesy Dustin Lynch

Luke Bryan and Dustin Lynch joined forces to pay tribute to Toby Keith during the 8th annual Crash My Playa destination event at Moon Palace Cancún in Mexico on Sunday (Jan. 22).

In the midst of Bryan’s headlining performance during the final night of the annual beachside concert getaway, he and Lynch performed a cover of Keith’s “Should’ve Been A Cowboy.” 

“The longest-standing representative of Crash My Playa. No one has drank more liquor, no one has vomited more, no one has taken more drugs, no one has taken more IVs, no one has passed more STD tests than this next gentlemen right here. He has got a clean bill, he does not have diseases, give it up for Dustin Lynch,” Bryan jokingly said as he introduced Lynch to the stage. 

“That’s going down in the history books of introductions right there,” Lynch said as he took the stage. “Crash My Playa, what’s up baby?”

Dustin Lynch, wearing a Silk Sonic t-shirt and baseball cap, joined Luke Bryan, who donned a colorful tropical print button-up, to belt out the lyrics to the Keith tune as thousands of fans watched from the sandy Cancún beach.

“I should’ve been a cowboy / I should’ve learned to rope and ride / Wearin’ my six-shooter, ridin’ my pony on a cattle drive / Stealin’ the young girls’ hearts / Just like Gene and Roy / Singin’ those campfire songs / Woah, I should’ve been a cowboy,” they sang as onlookers joined them in unison. 

Earlier in the day, Dustin Lynch hosted a rowdy pool party that included haircuts, mullets, a parade throughout the resort, drinking games and more.

Released in February of 1993, the song was Keith’s breakout hit from his self-titled debut album. 

The beloved country track was written solely by Keith and went on to become the most-played country song of the 1990s with more than 3 million spins. It hit No. 1 on Billboard’s US Hot Country Songs chart and became a minor crossover hit, reaching No. 93 on the US Hot 100. 

The inspiration for “Should’ve Been a Cowboy” came to Keith in the bathroom of a hotel in Dodge City, Kansas.

“A guy said to another guy, ‘In all honesty, you should’ve been a cowboy,’ when a girl didn’t dance with him in his hunting clothes. And I thought, ‘Man, that sounds like a song idea,’ and it was all over me,” Keith once recalled to The Oklahoman.

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“I went back and we were all two hunters to a room, and my roommate was Freddie Cortez. He’s passed away now, but he used to own Chastain’s and a bunch of country bars in town. Freddie went to sleep, and I didn’t want to wake him ‘cause he was hateful when you’d wake him up. I went in the bathroom, shut the door, wrote it down and put it in my bag and went hunting the next day. Came home, revisited it, and said ‘I’m gonna record this song.’”

The Oklahoma native added, “It’s the foundation for me of everything.”

Crash My Playa took place at the AAA Four Diamond awarded resort, Moon Palace Cancún, in Riviera Cancun, Mexico from January 19 through January 22, 2023.

Chris Stapleton, Cole Swindell, Lionel Richie, Dustin Lynch, Ashley McBryde, Brian Kelley, Carly Pearce, Chase Rice, Dylan Scott, DJ Rock, Kendell Marvel also performed during Crash My Playa.

Dubbed the ultimate vacation with Luke Bryan & Friends, Crash My Playa 2023 marked the third year that the event will be held at Moon Palace Cancún with the initial year being in 2020 and the eighth year of the event overall.

Fans in attendance were treated to an all-inclusive concert as well as enjoyed daily pool parties and other amenities offered by the resort, including a relaxing visit to the lavish AWE-Spa or a fun-filled outing at the 27-hole Jack Nicklaus Signature Golf Course.

For additional information on Crash My Playa visit their official website at www.crashmyplaya.com.

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Lauren Jo Black

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Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for Answers.com and her work being featured on Forbes.com. She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.