While in Buffalo, New York, McGraw and Kenny Chesney became involved in a scuffle with police officers after Chesney attempted to ride a police horse. McGraw came to Chesney's aid after police officers nearby believed the horse was being stolen and tried to arrest him. The two were arrested and charged with assault, but were later cleared. During a concert with the George Strait Country Music Festival several weeks later, Hill, dressed as a police officer, made an unscheduled appearance at the end of McGraw's set and led him off the stage.

When he was 22 years old and drunk, McGraw got a leprechaun wearing a cowboy hat tattooed on his thigh.

"She said, Rodeo man, where are you going?
Don't you know that the life of a cowboy is no good alone?
If you tear down that fence of rusty barbed wire
Then I'll lay down beside you and be your shotgun rider"

McGraw holds a pilot's license and has his own airplane, a single-engine Cirrus SR22. "When I quit drinking, it was a good diversion, a good way to focus on something," the country star says of flying.

In late 2004, his unlikely duet with hip hop artist Nelly became a crossover hit, spending 10 weeks atop the top 40 chart.

A minority owner of the Arena Football League's Nashville Kats, McGraw and his family could often be spotted at games until the team folded in 2007.

"And then she slides in and she gives you the green light
You hold off till you turn on the headlights
Someday when you're looking back on your life
At the memories, this is gonna be one of those nights
Yeah one of those nights"

Throughout the 2005 NFL season, McGraw sang an alternate version of "I Like It, I Love It" every week. The alternate lyrics, which changed each week, would make reference to plays during Sunday's games, and the song would be played alongside video highlights during halftime on Monday Night Football.

Swift wrote "Tim McGraw" during her freshman year of high school, knowing that she and her senior boyfriend would break up at the end of the year when he left for college. In the song, she sings: "When you think Tim McGraw, I hope you think of me."

McGraw had supporting roles in The Blind Side, Tomorrowland, and Four Christmases.