Back in 2000, Toby Keith was as red hot as red hot gets. Every song he released raced to the top of the charts. In fact, it was during that year that his "How Do You Like Me Now?" hung out at #1 for five consecutive weeks. He was untouchable.

That Time I Saw Toby Keith at the Very Beginning of His Career

When we got the sad news Tuesday morning that Toby had lost his battle with stomach cancer, I was immediately drawn to two HUGE Toby Keith memories.

Back in 1994, while attending the Country Radio Seminar, a bunch of us went into downtown Nashville to watch Mercury Records' Triple Play concert. It was a showcase for three of their newly-signed acts--Toby Keith, Shania Twain, and Jon Brannen.

I have no idea what became of Brannen, but we ALL know what became of the other two. It was a very cool evening that got cooler in retrospect as the years went by.

That Time Toby Keith Came to the Studio for a Live Interview

That brings me back to 2000 and my other big memory and my favorite one. Toby was set to perform at the Executive Inn Rivermont Showroom Lounge, and I had called his label to arrange an interview. Assuming they'd have no issue with a phone interview, I was bowled over when I was told, "Yeah, that's fine, but you'll have to come get him."

I quickly pieced together in my head that they thought I meant a live, in-studio situation. And when I did, I told them that that would be no problem at all. I went and got him in the WBKR van, brought him back, and the late Nick Weber, who was on that Saturday afternoon, did the honors.

That Time Toby Keith Bought a Bunch of Owensboro Barbecue for His Crew

Afterward, when we were in the van heading back, Toby mentioned he'd heard Owensboro was big on barbecue. After telling him that that was kind of an understatement, he asked if there was a barbecue place on the way back to the Big E. So I rolled through the Old Hickory drive-through, and he picked up a TON for his crew back at the Showroom Lounge. The staffers were craning their necks, and one asked, "Is that Toby Keith?" Sure 'nuff. And he was super gracious about the whole thing.

He was always a good dude. I met him on other occasions and he was perfectly hospitable every single time.

How sad to lose someone at such a relatively young age. But if you're a superstar musician, you always leave a legacy. And that's what Toby has done.

22 Photos of Toby Keith Young

Toby Keith was one of the most influential artists in country music history, with a career spanning from the mid 1990s all the way until his death in 2024. Let's take a walk back in time and see pictures of Toby Keith young.

Gallery Credit: Evan Paul

Toby Keith's 20 Best Songs Prove He's a Country Icon

Toby Keith reached No. 1 on the Billboard Country Airplay chart 20 times during his 30-plus year career, but some of this best songs were deep cuts.

Here are his greatest hits — the top songs from 19 studio albums and beyond.

Toby Keith died on Feb. 5, 2024 after a two-year battle with stomach cancer.

Gallery Credit: Billy Dukes

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