Toby Keith is the subject of a star-studded celebration slated for Monday in Nashville.

Ever-fascinating about the 20-time country music chart-topper, influential businessman, and philanthropist — who died on Feb. 5 after a nearly 20-month bout with stomach cancer — is how broad, yet deep were the friendships maintained by the "Should've Been a Cowboy" and "How Do You Like Me Now" singer.

It's logical that some of the performers at Monday's event, such as Luke Bryan, Eric Church, Darius Rucker and Carrie Underwood, should have longstanding relationships with the proud Oklahoman and global superstar.

However, there was also Keith's 30-year-friendship with Carrot Top that extended far past the comedian's appearance in the 2011 video for Keith's unexpected hit "Red Solo Cup."

In fact, before Keith's February passing, Carrot Top was the last artist to appear onstage and perform alongside Keith.

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It was one of many moments shared by the two performers, whose careers broke wide open to American stardom in the early 1990s.

Country singer-songwriter Toby Keithdies at 62

'90s country creates a fast friendship between Carrot Top and Toby Keith

Comedians and rising country stars of the era often shared identical tour itineraries. Keith, alongside top country stars like Dierks Bentley, Alan Jackson, and Keith Urban and rockers like REO Speedwagon, frequently saw Carrot Top's comic routine of the time, which included the now 59-year-old performer, born Scott Thompson, appearing onstage in drag.

Upon their first meeting, Keith, taking a liking to the fellow rising star — and noting that Thompson's father was a longtime country music fanatic — gave him a signed CD copy of his eponymously titled debut album from the trunk of his car.

During his childhood in Brevard County, Florida, Carrot Top and his father listened to artists such as Conway Twitty, Merle Haggard, and Willie Nelson. However, Keith became his modern favorite.

For Carrot Top, a song like the 2003 Willie Nelson duet "Beer for My Horses," which the comedian often plays to close his sets, showcases how well Keith's work honors his appreciation for his fellow Americans.

"You can't play a Toby Keith hit and not expect to hear part of that crowd cheer very loudly in appreciation," he adds.

"Toby was a performer with larger-than-life charisma and an artist with a distinctive, fun style."

'Red Solo Cup' filled Toby Keith and Carrot Top with friendship

"Red Solo Cup" is a song that Keith himself often referred to as "the stupidest song I ever heard in my life." Penned by Brett Warren, Brad Warren, Brett Beavers, and Jim Beavers and released in October 2011, it took six months to peak in the Top 10 on country radio and a year to hit the Top 20 on Billboard's all-genre Hot 100 charts.

Part of its popularity was a wild party video featuring Carrot Top and a who's who of three decades of superstars — and acquaintances and friends of Keith — including magician Lance Burton, ventriloquist Jeff Dunham, television host Craig Ferguson, athletes Larry Bird and Roger Clemens and musicians Ted Nugent, Sammy Hagar, Eric Church, and Joe Nichols.

Crafting a video for "Red Solo Cup" wasn't exactly high on Keith's list of priorities. He pitched the idea to Carrot Top almost offhandedly, suggesting that he would not be offended if appearing in it didn't fit into Carrot Top's schedule.

"This one could be the dumbest hit song I'll ever have in my career, so something tells me I should do a ... video for it," Carrot Top remembers Keith joking.

Keith played and sang him a few bars of the song over the phone. Carrot Top immediately decided that he was into whatever Keith was trying to accomplish with the song.

Though he couldn't be present for the shoot, Carrot Top contributed hilarious candid footage that he shot at home.

Toby Keith and Carrot Top rekindled friendship in Las Vegas

Over two decades, the pair frequently rekindled their friendship at award shows and in the early 2000s when both had concert dates in Las Vegas.

At 2014's "ACM Presents: An All-Star Salute to the Troops" in Las Vegas, Carrot Top recalls that Keith performed his 2003 hit "American Soldier" before he was presented with the Spirit of the USO Award for having played 200 shows and entertained more than 250,000 men and women in uniform and their families.

"It was so beautiful. I remember jumping up while nobody else was standing, and he saw me, stared right at me and (deadpanned) into the microphone, 'Thanks, Carrot Top.'"

Upon joining him backstage, Keith was far more animated and legitimately touched by the moment.

"Thanks ... for being the only one willing to stand up for me out there," the comedian recalls the country icon saying.

As a show of goodwill, Keith brought his wife and entire touring support team to Carrot Top's comedy show the next night.

"Whenever he was in Las Vegas, Toby must've seen me at least a dozen times — to see my show or grab lunch with me — after that. In fact, he saw me so much that whenever I had a new joke in the routine, I'd call Toby and run it by him."

Toby Keith and Carrot Top share one final performance

Though he had been diagnosed with stomach cancer, Keith was still maintaining a busy touring schedule.

In November 2022, Keith received BMI's Country Icon award. That honor has previously been received by names including Merle Haggard, Loretta Lynn, Willie Nelson, and Dolly Parton.

The event also honored the 30th anniversary of the three-time BMI Country Songwriter of the Year's recording of the hit single "Should've Been a Cowboy."

In September 2023, Keith appeared during the NBC broadcast of the "People's Choice Country Awards" at the Grand OIe Opry.

At the event, he offered a moving performance of "Don't Let the Old Man In" from Clint Eastwood's 2018 film "The Mule."

He kicked off this year by attempting a few Vegas performance dates.

Keith called Carrot Top to take part in his second date at the Dolby Live Theater at the Park MGM Hotel and Casino.

Though their schedules initially conflicted, they made it happen.

“I was also performing somewhere else that night," Carrot Top recalled to the Keep It Truckin' pod and videocast. "So he let his show run long enough for me to run in the building, literally. When I showed up, he immediately said ‘Carrot Top is in the house,’ then he put his arm around me and we sang 'Courtesy of the Red White and Blue.’

“The last song he ever sang was on stage was with me.”

He added: "Toby was a true patriot who loved America and his fans."

'Toby Keith: American Icon'

Luke Bryan, Eric Church, Ashley McBryde, Parker McCollum, Jelly Roll, Darius Rucker, Carrie Underwood, Lainey Wilson, the War and Treaty and more will honor Keith at the "Toby Keith: American Icon" event on Monday, July 29 at Bridgestone Arena.

Related to the event, at 2022's BMI Country Awards, Keith was feted onstage by artists, including Carrie Underwood, who offered a spirited rendition of "Should've Been a Cowboy," plus Eric Church, who performed a stripped-down version of Keith's 2003 hit "I Love This Bar."

A portion of the ticket sales will benefit the Toby Keith Foundation's OK Kids Korral, a cost-free home for families of children dealing with critical illnesses, and the Monroe Carell Jr. Children's Hospital at Vanderbilt, one of the nation's leading children's hospitals.

The "Toby Keith: American Icon" event will be recorded that evening and broadcast on NBC on Aug. 28, from 9-11 p.m. ET.