Randy Houser is just one of the new crop of artists hanging out at Tootsie's Orchid Lounge these days, and he and his buddies will no doubt provide the famed 50-year-old watering hole with a whole new set of stories and legends before his performing days are through.

The historic bar, located on Nashville's lower Broadway, has been a favorite hang for both wannabes and famous artists alike for more than five decades now, and nearly every country artist in the business who has played the Ryman Auditorium has taken those 37 steps across the alley to grab a cold one after his or her show and to soak in the atmosphere of the legendary dive.

You never know who you'll run into at the bar -- just ask Randy. Fresh off the bus, the aspiring singer was new in town, and on his first Tootsie's visit, found himself seated next to Toby Keith and was treated to a beer by the superstar. In honor of the famed lounge's 50th birthday celebration, The Boot talked to several artists who recalled their favorite memories of Nashville's famed purple landmark.

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Randy wandered into Tootsie's his first week in town, and has been hanging out at the bar with buddy Jamey Johnson and others ever since. "It's funny how things come full circle. When I first come to town I was hanging out the first week at Tootsie's and Toby Keith came in. I was leaned over the bar and kind of minding my own business, and he finally just kind of nudged me and said, 'What are you doing here?' And I said, 'Well, I just moved to town.' He asked when and I said, 'This week,' and he said, 'How's everything going? Where you from?' I told him Mississippi, and he said, 'Well, lemme buy you a beer.' So, he bought me a beer and we chatted for just a second, and I didn't bother him and he left, and now here it is almost 10 years later and I'm on his record label! He doesn't even know I remember that story!"

Little Jimmy Dickens spent many hours at Tootsie's back in the bar's heyday during the '60's and '70's, and recognizes how key the place was in nurturing some of the greatest songwriters in the history of country music. "The first thing I know about Tootsie's is I feel like I came with the building!" the country legend tells The Boot. "I've been with the Grand Ole Opry 62 years, and if you missed a friend backstage, you knew where to go look for them. Because they would be in Tootsie's visiting with one another, trading songs around or having a beer and visiting with one another, and I think that's one of the greatest things that ever happened to country music, because these songwriters all got together and wrote these beautiful songs that we hear today. As far as getting stuck with the hatpin by Tootsie, I was lucky, I never did get out of line! 'Cause I learned early, you don't do that!"

Ira Dean
has not only spent many a night in the Orchid Lounge getting a little sideways on occasion, he has also written many a song in the bar. "I remember going into Tootsie's, I just never remember leaving," he jokes. "I've paid the rent in that place many, many nights over the years I've been in town. That's one of the places I played there when I first came to town, and it hasn't changed a bit. Me and Mel Tillis have gone in there and tried to drink 'em out of beers many nights. That's our hangout. As a songwriter, too, I've been in there at noon writing. I've written many songs in there. I can't remember how they go! [laughs] Tootsie's is my second home. It's great to have a place that stays the same. Usually a bar changes décor, it'll reinvent itself every four or five years just to try and keep business going. But that place is the same since I moved here. The stories and the history in there ... Nashville just wouldn't be the same without Tootsie's. It was really nice of them to call me and be part of [the anniversary celebration] I think I might have an outstanding bar tab or something so they wanted me to come here. Tootsie's is haunted by the ghost of my liver, 'cause it died in there! They were talking about ghost stories earlier, it's haunted by the ghost of Ira's liver past!"

Andrew Southam

Terri Clark performed at the Orchid Lounge for years at the start of her career, but only during the daylight hours, under strict orders from her mom. "I didn't see a lot of shows because I was forbidden to go after dark," Terry tells The Boot with a laugh. "I remember one time they needed someone to fill in because one of their players didn't show up. I said, 'If you send somebody to get me, I'll play.' I didn't have a car, so I always had to take the bus to the bus stop at the end of Broadway and walk. I said, 'If you come to my door and pick me up and bring me to the bar, 'cause if my mom finds out, I'm in trouble!' That's the only time I ever played at night there, and I don't think I ever told her about that. I made a lot more money that night, though!"

Mark Chesnutt especially loves Tootsie's for its amazing heritage and colorful past, of which he's a part, since he reportedly clobbered another patron of the bar one night while passing through town on a gig. "My favorite Tootsie's story isn't even true," says Mark. "Ever since I've been coming to Nashville in the '80's, I've made it a point to hang out at Tootsie's. Even when this part of town wasn't safe to be in, I was still coming down here. When I had the opportunity to play the Ryman for the first time, I made it a point to go across the alley and keep the tradition going. I've done that ever since. Every time I play the Ryman I always go across the alley. I did that one night after playing the Ryman, and I left town. The next day, I heard it was all in the news that I had gotten in a fight in the alley outside of Tootsie's; that some guy was picking on me and I supposedly beat him up. And I won. The police came and arrested the guy and all that, but that never happened. I've never gotten in a fight at Tootsie's! Everybody's always been fun hanging out in there."

Singer John Stone has spent years honing his craft onstage at the legendary dive, and gets choked up thinking about one particular night when one of the bar's most famous patrons was honored for all this achievements. "It's amazing that Tootsie's is recognized worldwide," he says. "Kris Kristofferson used to sweep the floor there. This is a great quote from him. They dedicated a plaque in the floor to Kris a few years back, and when they did that ceremony, I got to dedicate this plaque personally to Kris. I was standing onstage and I gave a little speech, and handed him the plaque, and they unveiled this marble tile in the floor that has his face on it. The year he got inducted into the Country Music Hall of Fame, they did it there. He looked down, and he was so honest and sincere, he kind of looked at it and said, 'I can't believe I've got my face on the floor that I used to sweep!' I thought, 'That's a moment that will stay with me for a long time!'"

"I remember being onstage playing and Kid Rock and Hank [Williams] Jr. came in," John continues. "They got up and jammed with us for about two hours. People were standing on each other's shoulders inside, and there were 3,000 people on the sidewalk trying to get in! Cars were having to drive around people on the road. It was unreal. We had Kenny Chesney and Steve Miller in here onstage at the same time one night with us. It was just crazy. That happens all the time. That's why Tootsie's is Tootsie's."