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Toby Keith was an incredibly country music artist, but by all accounts, he was an even better man. First and foremost before we get into this post, I want to wish everyone who is the military, and/or has lost someone who served in the armed forces, a happy Memorial Day. It’s a somber day, but also a very important day for all of us Americans to take a moment and really appreciate, as much as we should every day, all of the sacrifices the men in women and uniform have made for us on behalf of our freedom. These brave men and women paid the ultimate price. Freedom isn’t free. : kristy.hazii (TT) pic.twitter.com/571tJniMo2 — Whiskey Riff (@WhiskeyRiff) May 26, 2025 Many country artists dedicate a lot of time and effort into honoring the military, but no one did more than the great Toby Keith, who was a part of 18 USO tours during his life, and played for over 250,000 military service members when you combine all of those trips together. Despite having to go into war areas (and having plenty of stories to prove it), Keith never once doubted the good work he was doing. He said this when he was asked about USO tours by On Patrol in 2008: “I’ve got a family back home too, that starts to freak a bit when it gets to this time of year to come over here. Once we’re gone, we’re over here, even after seven years, you still have to get your mind set that you’re going to be in a chopper, in a war zone, you’re going to come under fire sometimes. You’re going to be involved in some stuff. But the second that it gets too hot, I look up and here comes a Cobra or an Apache (helicopter) to take us on in. You know they (armed forces) are going to make sure you’re taken care of.” He was never afraid to go into active war zones in the Middle East, and during an appearance on the Drifting Cowboy podcast recently, Toby’s longtime friend Cledus T. Judd, whose real name is James Barry Poole, talked about his friend and his deep love and admiration for the military. Toby had asked Cledus many time to go overseas with him, though he told Toby he was “a big sissy” and planned to stay in the USA. During the height of the war in the Middle East, I can see being scared and not wanting to go, so I completely appreciate the honesty, but it makes how much Toby went over there and did for the troops, especially during that time, all the more impressive. Cledus joked that told Toby all the time he needed to just “get a timeshare over in Iraq” because of how much time he spent over there: “I always said, ‘Toby, you need to get you a timeshare over in Iraq.’ Because, hell, he spent most of his time over there. He tried to get me to go over there two or three different times, and I said, ‘Look here, hoss, you braver than me. I’m a big sissy. [I’ll] stay right over here in the US of A, and you go over there and handle them troops and I’ll hold the fort down here.’ I never had the balls to go do it.” Podcast host Dillon Weldon said he’d heard stories from Toby’s close friends who had gone with him before about bombs going over their head, and getting dropped off in the desert in the middle of nowhere: “TK and Kurt, I went to have lunch with the, they were telling me some of those stories of being over there. Bombs going over, being dropped off in the desert in the middle of nowhere.” Cledus explained that it didn’t phase Toby in the least: “Didn’t phase Toby Keith. He’s just a big old boy. He can handle himself, I promise you.” It’s just hard to wrap your brain around, but he was one of one, and had a deep love for this country and the people who defend it. Impressive is a massive understatement. The podcast clip also showed vintage footage of Keith talking about why his work with the USO was so important, which stemmed from the fact that his own father was in the Army: “My dad was a soldier, so my heart person foremost was always with the Army. But getting out here and meeting all the military, I’ve got a whole new respect for the whole organization. We just like to bring a piece of home here and hope everybody take time off from the war, and kick back a little bit and have some entertainment just like they would have at home. It didn’t take very long at all to realize how appreciative they are that somebody does take time out of their life to come over here.” Hearing from Toby’s friends about the kind of man he really was behind closed doors, and how it truly matched the persona he presented to the world, is so refreshing, and there really will never be another one like him. Check out the clip here: @dillon.weldon Toby Keith was a true patriot. #tobykeith #uso #cledustjudd #countrymusic #foryou #fyp ♬ original sound – Dillon Weldon Toby was a true patriot, who put himself in harm’s way when many others wouldn’t even dream of it, to bring troops fighting horrific wars a small sense of normalcy, or even just some fun, and that makes more of a difference than most people can imagine. Of course, Toby penned and recorded many patriotic songs throughout his legendary career, but I have to leave you with this one on the Memorial Day weekend: “Courtesy Of The Red, White And Blue (The Angry American)” The post “He Needed A Timeshare In Iraq”- Toby Keith’s Longtime Friend Recalls The Amount Of Time He Spent Performing For Troops In Active War Zones first appeared on Whiskey Riff.