July 21

Tim McGraw’s “The Last Dollar (Fly Away):” A Bad Luck Led To A Huge Hit

It was fourteen years ago when Tim McGraw’s “The Last Dollar (Fly Away)” hit the top spot of Billboard’s Hot Country Songs charts, becoming the first among Tim McGraw songs to hit No. 1 on the country charts since “Back When” in late 2004.

Written by Big Kenny – one half of the country-rock duo Big & Rich – “The Last Dollar (Fly Away)” tells the tale of a man who stays upbeat even though he has nothing left but a dollar. 

Big Kenny wrote the country ballad on New Year’s Eve in 2002, after a terrible night of gambling in Las Vegas. He and his manager were in America’s gambling capital to open the “Alabama Farewell Tour.”

At that time, Big Kenny was just a struggling artist with only $200 to his name, and credit cards maxed out at $140,000. He had spent all of his money making their records and just living until he would “finally be good enough to be the ones on the big stage.”

With not enough money to cover his entire trip, Big Kenny decided to try his luck on blackjack tables. In the beginning, he was making it big, winning nearly $1,000. Unfortunately, as he continued playing, he eventually lost everything except for $21. He generously left the dealer with a tip of $20, giving him a dollar to his name.

Though the devastating experience hit him “like a ton of bricks,” that realization came with the liberty of understanding that, after all, he had nothing to lose – at the same time, it was a driving force behind his dedication to his artistry.

From that point, Big Kenny’s career took off. Tim McGraw recorded the up-tempo ballad with his three daughters singing on its final chorus. 

You can listen to “The Last Dollar (Fly Away) by Tim McGraw” in the video below. It’s one of the gambling songs that you won’t think could give you enough hope to keep going.


tim mcgraw

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