Barstool Sports’ Dave Portnoy Shares Memory Of Meeting Toby Keith

Author Lauren Hoffman

February 7th 4:09 PM

The country music community, along with fans and celebrities across the nation, are mourning the loss of Toby Keith following his passing on February 6. One fan in particular is the owner and founder of Barstool Sports, Dave Portnoy.

RELATED: Toby Keith Says “You Have To Be The Captain Of Your Ship”

On the recent episode of Barstool Rundown, Portnoy shared the story of the first time he had met Keith while out to dinner in Nashville. The 46-year-old said it was “unbelievable” and that he had the opportunity to speak to him for almost two hours.

“RIP Toby Keith. I was lucky enough to see him do a surprise performance at Jeff Ruby’s Steakhouse a few years ago. I talked to him for hours about how much he hated Lincoln Riley + loved the troops. He left such a positive impression on me I listed him as 1 of my top 10 Americans,” Portnoy shared on X.

RIP Toby Keith pic.twitter.com/6ZYRDp7JKf
— Dave Portnoy (@stoolpresidente) February 6, 2024

Portnoy has always been a fan of Keith. However, he admitted during the Barstool Sports clip that he has gotten more into country music as he’s gotten older. He even gives his co-hosts on the show a lesson on Keith and sings one of his greatest hits, “How Do You Like Me Now?!” (well, he tries to do so).

Back in 2022, Portnoy unveiled his Top 10 Americans list, which had Keith in the No. 9 spot at the time. Portnoy’s fellow host, Kayce Smith, of the Barstool College Football Show crew, also shared her list back in the day and included another country legend, Dolly Parton.

Keith, who we lost yesterday at the age of 62, died peacefully surrounded by his family. The country singer had been fighting a battle with stomach cancer since 2022 and is survived by his wife Tricia, and three children, Shelley, Krystal, and Stelen.

Click here to see more as we remember the legend himself, Toby Keith.

.@stoolpresidente:

1. Any Army Man
2. Pat Tillman
3. Teddy Roosevelt
4. Roger Stauback
5. Steve Sabol
6. Charles Barkley
7. Joey Chestnut
8. Taylor Swift
9. Toby Keith
10. Deion Sanders
— Barstool Sports (@barstoolsports) December 10, 2022

Five of Toby Keith's Songs That Will Live Forever

"Should've Been a Cowboy" (1993)
This is his debut single and the song people will always associate with Toby. Many artists mentioned the song and its lyrics in their tribute to him after his death (2/6). Keith wrote the song himself, and it has always been his anthem. The song has received more than three million spins on country radio, making it the most-played country song of the 1990s. Over the years, the song has been a staple following sporting events at Oklahoma State University (home of the Cowboys), often played over the venue’s PA system several times in succession as fans emptied the stadium or arena.
"How Do You Like Me Now?!" (1999)
This song brought Keith to superstardom. Toby told me the inspiration for the song in 2000. “Initially, I said, ‘Here’s my title: ‘You Never Loved Me Before, So How Do You Like Me Now?’ It’s one of my catchphrases. A lot of people become successful after they’ve been told they won’t ever be so that people can relate to this. It can be about an old flame or a boss or a teacher -whatever it means to each individual. It was a fun song to write.”
"I Wanna Talk About Me" (2001)
This is another fun song and a big hit for Keith. The song was originally pitched to Blake Shelton, whose label turned it down. After recording the song, Keith said he knew he would get banged around for the song a bit. He noted, “They’re going to call it a rap, [although] there ain’t nobody doing rap who would call it a rap.”

The music video for the song shows Toby in many different situations, including a man shopping with his girlfriend or wife, a police officer, a motorcycle rider, and a surgeon.
"Courtesy of the Red, White, and Blue (The Angry American)" (2002)
The song he wrote after the 9/11 attacks on America and was also inspired by Keith’s father’s death in March 2001. In a November 2003 interview with CBS, Keith said of writing the song: “I was so angry when we were attacked here on American soil that it leaked out of me.”

The music video for the song features Toby performing the song, playing a red, white, and blue guitar, and showing images of his own father fighting in a war.
"Red Solo Cup" (2011)
Keith sure is good at fun party songs, and he proved it once again with this song, which was the only song on the album Clancy’s Tavern that he did not write. The song was written by the Warren Brothers in Nashville.

The music video includes cameos from Jeff Dunham (and his character Bubba J), Carrot Top, Ted Nugent, Sammy Hagar, Craig Ferguson, Geoff Peterson, Roger Clemens, Eric Church, Joe Nichols, Lance Burton, and Larry Bird, among others.