To put things plainly, the 1990s were simpler times. The food tasted better. The people were friendlier. The country music was next level. That’s at least how it seems as we look back on that period, right? It’s easy to look at the 90s through rose colored glasses, but then you see videos like this one of Toby Keith and Troy Aikman (who was then quarterbacking the Dallas Cowboys) and it really does seem like it was the best decade of all time. The Big Dog Daddy loved him some Dallas Cowboys, and he and Troy Aikman became friends. Keith was interested in the NFL, and Aikman loved country music and even wanted to try his hand in making his own (more on that later). And at one point in 1994, Aikman got a front row seat to a performance of what was then a freshly released hit song “Should’ve Been A Cowboy.” Keith describes the song in the video as the track that “took us off hamburger and put us on T-Bone,” which got a laugh out of Troy Aikman. The Dallas Cowboys star also chuckled later in the song when the Big Dog Daddy ad-libbed a portion of the chorus and changed it to “Should’ve Been A Redskin,” which was one of Dallas’ biggest rivalries back in the day. It’s a blast from the past, and whole lot of fun to watch and reminisce on: “Toby Keith might’ve been born and bred in Oklahoma, but he had a soft spot for the Dallas Cowboys just down the road. A proud Sooners fan in college ball, he still backed America’s Team on Sundays, performing at Texas Stadium and later AT&T Stadium for big games and halftime shows. He struck up a friendship with Troy Aikman and was a familiar face on the sidelines through the years.” View this post on Instagram A post shared by Truck Stop Chic (@truckstopchic) Now, let’s get to that country music career of Troy Aikman’s, shall we? The former quarterback and current NFL analyst spoke with the Sports Illustrated Media Podcast back in 2021 about the off-ramp he took into the country music space at one point. He was very frank about it, and said that he doesn’t look back fondly on it: “You know, they always say ‘stay in your lane.’ I kind of like my lane, Jimmy. I try to stay in it. Not to say that over the years, I’ve been asked to do cameos and Jerry Maguire and different things. I’ve done a country and Western album. It was awful. I don’t even know if they call it ‘country and Western’ anymore. It was a country album, I should say.” Yeah if you are to give it a listen, I’m not even sure you could call it music. As for when those country music projects came up, and why Aikman decided to do them, the former Cowboy said that he felt as though he had to take advantage of the opportunities that were presented to him. That’s why he did a song with Waylon Jennings, and another with Toby Keith: “I did one after our first Super Bowl, a bunch of us Cowboys, (Jay) Novacek, Joe Avezzano, our special teams coach, and some other people did it, Randy White. And then in the mid-’90s, toward the end of my career, I did a song with Waylon Jennings and did another one with Toby Keith. Not that I’ve ever aspired to be a singer. I can’t sing at all. But just some opportunities that come up, and you say, ‘Yeah, let’s do it.’ You never know when these things might come up again, so you do them.” Want to hear some of Troy Aikman’s work? It’s honestly really funny to imagine the Troy Aikman that calls NFL games alongside Joe Buck for ESPN singing country music. Saying the word “singing” there is probably generous… but if you are brave enough, you can check out some of his country music work below. The first is the song he did with his good friend Toby Keith. “Two Pairs of Levis” How about that? And just for good measure, I’m gonna link Troy Aikman’s “Oklahoma Nights” from the Super Boys project Everybody Wants To Be A Cowboy. It’s… certainly something. “Oklahoma Nights” The post Remember When Country Star Toby Keith & Dallas Cowboys QB Troy Aikman Released A Song Together? first appeared on Whiskey Riff.