Living The Dream: Longtime Chicago Cubs Organist Gary Pressy Reflects On His Career

"I am very lucky and very blessed that I get to do a job that I wanted to do since I was five years old. I kid you not."

Legendary organist Gary Pressy has already had a busy day. After a congested drive in from the suburbs of Chicago, Pressy has already partaken in an important meeting with the iconic muppet Cookie Monster, who on this particular day will serve as the featured vocalist for this afternoon’s seventh inning stretch of "Take Me Out to the Ballgame" at the Friendly Confines of Wrigley Field.

Pressy quickly apologizes for being a few minutes late for our interview and walks briskly through the hallways of the somewhat dated press area that sit atop of the renovated ballpark.

"I have played in 2,653 straight games," he says with a sly smile, trying his best not to brag. "I got the job in 1987 and I haven’t missed a game since."

The 62-year-old gingerly walks into his office, or rather a small and somewhat cramped press box, and sets down his lunch plate of sloppy joes and the sheet music he had been holding under his arm. He looks down onto the field where die-hard fans are beginning to gather before the game to catch batting practice and then glances at his trusty Lowrey organ that sits just a few feet away.

It’s the calm before the sweet chaos of a ball game.

Pressy seems to welcome the excuse to to enjoy a little down time before he starts his job of providing a portion of the background music to not only the Chicago Cubs baseball team, but to all of their fans who travel to the ballpark to hear it.

"There are a lot of people who work for a living and its absolute drudgery for them every single day," he says as a DJ plays Bob Seger and the Silver Bullet Band’s hit "Old Time Rock and Roll" in the background. "I am very lucky and very blessed that I get to do a job that I wanted to do since I was five years old. I kid you not."

Indeed, the longtime organist is one of the many pieces of tradition and nostalgia that fills Wrigley Field on a daily basis. From the ivy to the scoreboard to a kid that grew up wanting to play the organ for a sports team, Pressy is the first to admit that this gig is a dream come true.

Pressy started playing the organ when he was just a youngster growing up in the suburbs of Chicago. He would spend his afternoons trying to imitate the organist he would hear during the radio broadcasts of the games in an attempt to name the music they were playing.

Heck, the garage of his childhood home even had vine on its walls.

Pressy would continue playing the organ while attending St. Laurence High School, from which he graduated in 1975. When it was time for college, he instead decided to take private organ lessons from a teacher named Russ Caifano. And when it was time to get a job, he sent his resumes out to various sports teams in Chicago that possibly needed an organist.

As fate would have it, the Chicago Sting soccer club needed one, and a man by the name of John McDonough hired him. And when the well-known executive moved over to take a front office job within the Chicago Cubs organization, he brought Pressy along with him.

And the rest is history.

"When I first started playing here in 1987, I would say it was strictly 90% organ music, both in terms of the pregame and during the game," recalls Pressy, who ranks the Chicago Cubs World Series run back in 2016 as one of the highlights of his career. "But then we put the new screens up in the outfield in 2015 and then we added the DJ…"

His voice begins to trail off, but that’s not to assume that he has been against change.

"The players love hearing their music play for batting practice and for their walkup songs, and that’s good," he says quickly. "If it gets them going and they get a base hit out of it, that’s what we want."

Pressy lets out a laugh as he looks down on the crowd once again that is beginning to gather on this sunny and warm day in Chicago. And then he continues speaking, further stating the importance of him evolving with the times a bit in terms of the music he plays.

"You don’t want to sound like a broken record, you know?" he says. "You have to update your music, so I will listen to the top 40 and such. I mean, I still have to go back to the forties for some of the music, but I know play Lady Gaga songs and Katy Perry songs. Nobody wants to get stale. The challenge is always to improve yourself if you can and improve your work. Hopefully, I’ve done that."

In recent years, he does this in perfect harmony with the disc jockey and continues to become more accustomed to working with someone else to provide the music for the ballpark.

"We switch back and forth throughout the game and I think it pleases everyone who comes to the park,” he says. “We kind of know what the other one is going to do and when I’m going to jump in. But yeah, I think it’s a good thing. I mean, you have 3-year-olds and 85-year-olds out in that crowd. It’s a good blend."

And whether he's collaborating with a DJ or not, Pressy says he has reached that sweet stage of his career when things have become somewhat spontaneous when he sits down at that organ and plays.

"I do use the music sheets sometimes since I have to keep the sheet company in business," he laughs. “But yes, a lot of the music is spontaneous and it comes based on something that is happening on the field, especially if there is a song connected to it.”

Because yes, he not only plays the organ, but has to keep his eye on what’s happening on the field.

“It really helps that I have always been a baseball fan,” he says. “I’ll know when a batter has three balls on him and the next pitch could be a walk, so you are going to need to play a walking song. And you have to just know things like how you don’t play when the pitcher is about to throw the ball. There are a lot of rules that you have to follow.”

It makes one wonder if anyone will ever be able to truly take Pressy’s place.

“On a sunny day, there is nothing better than being at Wrigley Field,” he says as he stands up, looking as if he is ready to get this game rolling. “You have to be a fan and you have to care because if you’re not, the music will fall flat. Whether you are playing the piano or organ, I truly believe that the instrument reflects how you feel. I love it here and I hope I’m coming across like that.”

So, how long will he be doing this? How long will he remain the Chicago Cubs organist, the player of the music that serves as the soundtrack to one of the most major teams in one of the greatest metropolises in the entire country?

“We will see,” he says, taking a long deep breath of the humid air that begins to fill his haven above the seats. “I would love to be around for another [World Series] parade... I guess I’m going to do it till I get it right.”

Mission accomplished, sir.

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Living The Dream: Longtime Chicago Cubs Organist Gary Pressy Reflects On His Career

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