Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

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

Tim McGraw's "The Last Dollar (Fly Away)"
by

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.

Latest Stories

Zach Bryan + Pink Skies

Zach Bryan’s “Pink Skies” Explores Loss and Love

Country music singer-songwriter Zach Bryan released “Pink Skies” as part of his album of the same title. It immediately became the talk of the town because of the (definitely not ...

Hank Williams - Hey Good Lookin'

Hank Williams’ Relatable Charm in “Hey, Good Lookin’” 

When Hank Williams arrived in 1949 in Nashville, he didn’t wait long to become one of the biggest stars in country music. A year later until 1951, he enjoyed the ...

Cavendish Beach Musical Festival 2024

Cavendish Beach Music Festival 2024: What You Need To Know

Festival Title:Cavendish Beach Music Festival 2024Festival Duration:July 5-7, 2024Venue:Route 6 Ranch in Cavendish, Prince Edward Island, CanadaPerformers Include:Brothers Osborne, Tyler Childers, Zac Brown Band, and moreTicket Information:Get Your Tickets Here ...

Willie Nelson's 4th of July Picnic 2024

Willie Nelson’s 4th of July Picnic 2024: What You Need To Know

Festival Title:Willie Nelson’s 4th of July Picnic 2024Festival Duration:July 4, 2024Venue:Freedom Mortgage Pavilion in Camden, New JerseyPerformers Include:Willie Nelson, Bob Dylan, Robert Plant & Alison Krauss, and moreTicket Information:Get Your ...

Travis Tritt + Help Me Hold On

Travis Tritt Begs His Lover For One More Chance In “Help Me Hold On”

Country singer Travis Tritt scored his first number-one hit with his second release from his 1990 debut album Country Club titled “Help Me Hold On.” He co-wrote it with accomplished ...

Carrie Underwood Falls Off Stage on Tail End of South Carolina Concert

Carrie Underwood Rocks Carolina Country Music Fest Despite Rain

Country singer Carrie Underwood graced the last day stage of the Carolina Country Music Fest 2024 in Myrtle Beach and delivered one hell of a performance despite the massive downpour. ...

Billy Ray Cyrus Files for Divorce from Firerose, Seeks Annulment on Grounds of Fraud

Billy Ray Cyrus Files for Divorce from Firerose, Cites Fraud

American country singer Billy Ray Cyrus reached a breaking point with Australian singer Firerose just after seven months of marriage. According to court documents obtained by the Associated Press, Billy ...

Travis Tritt + Best of Intentions

Travis Tritt Made A Career Comeback With “Best of Intentions”

It was 2000, and it had been six years since Travis Tritt hit the top of the charts and three since his last appearance in the Top 10. The first ...

Sonny James Death

A Moment To Remember: Country Singer Sonny James’ Death At 87

Country singer Sonny James, known for his 1957 track “Young Love,” which topped both country and pop charts, passed away on February 22, 2016, at Nashville’s Alive Hospice. According to ...

Wynonna Sings Coal Miner's Daughter with Loretta Lynn's Granddaughter Emmy Russell - Idol

Wynonna Judd Joins Emmy Russell On Idol To Sing “Coal Miner’s Daughter”

Emmy Russell started her American Idol journey with an original song. She fittingly ended it with a tribute cover of “Coal Miner’s Daughter” for her late grandmother and country legend ...