@frankiejustinmusic / TikTok & Matthew J. Lee / The Boston Globe via Getty Images

Play Singon Amazon Music Unlimited (ad)What a way to honor the late and great Toby Keith!

Since Toby Keith’s passing in February, his supporters worldwide have found special ways to honor him.

One repeated way individuals seem to do this is by singing a tribute to the Oklahoma native with his everlasting track, “Should’ve Been A Cowboy.”

Many of country music’s own stars have honored Toby with a cover of the popular song, including Luke Combs, Carrie Underwood, and Tracy Lawrence.

Given that “Should’ve Been A Cowboy” was one of Toby Keith’s most iconic songs, it’s fitting that its legacy lives on.

The Story Behind “Should’ve Been A Cowboy”

“Should’ve Been A Cowboy” was actually Toby Keith’s debut single. He rose to fame with its release in 1993. The song ranked among the most popular tracks of the 1990s, garnering over three million plays on country radio.

On January 3, 2024, just one month before Toby Keith passed away, he revealed the story behind “Should’ve Been A Cowboy” in a video posted on his social media.

During a hunting trip in Dodge City, Kansas, Toby and his friends watched as a fellow hunter was rejected by a cowgirl. A friend jokingly said, “John, you should’ve been a cowboy,” sparking the idea for the song.

Toby recalled, “So I thought, ‘I’m going to write that.’ I took my guitar, sat on the side of the motel tub, and shut the door so no one could hear me.”

And just like that, Toby wrote the song in just 20 minutes, and it became a defining hit in his career.

Did you know? Toby Keith was only 14 years old when he wrote his first song.

Entire Plane Sings Tribute To Toby Keith

A fun video was recently posted to the TikTok account @frankiejustinmusic, who in his bio, refers to himself as a “3rd generation horseman who sings country music.”

The video shows Frankie at the front of a plane, which is running late on its trip to Nashville, Tennessee. Standing beside him, a flight attendant holds the intercom up to him. For a fun surprise, the whole plane joined Frankie for a Toby Keith sing-a-long. The song choice? You guessed it! Toby Keith’s “Should’ve Been A Cowboy.”

As soon as Frankie sang the first line of the song, the passengers started to immediately cheer. As he got to the chorus, he yelled, “Sing it now!” and they started singing along with him.

The caption on his video read:

“Only on flights to Nashville do they ask ya to sing for the plane. God Bless Toby Keith!”

Over the video, there is text that reads, “When your flight to Nashville is late so they ask you to sing for the plane.”

Throughout the 46-second video, you can see phones of the passengers in almost every row recording Frankie at the front.

With thousands of views already, Toby’s team even shared the video on his Instagram story!

Toby Keith / Instagram