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The View From Up Top: The Wrigley Field Experience Through The Eyes Of Chicago Cubs Organist Gary Pressy

Few things are consistent in life. Fortunately, Wrigley Field is a place of consistencies. Ivy on the wall, the Centerfield scoreboard, the bright red marquee on Addison & Clark, and Gary Pressy playing the organ.

Pressy has been the Cubs organist since 1987 and has yet to miss a game.

As he celebrates his 30th year with the Cubs, I caught up with Pressy to get his view from the press box on how he decides what songs to play, his favorite celebrity encounter, the World Series victory, what he listens to in his spare time, and more.

Some musicians dream of playing in front of sold out arenas, concert halls, or being the first chair in a symphony. For Pressy, he always dreamed of being the Cubs organist.

“When I was 5, I’d be in the backyard imitating Jack Brickhouse, Ernie Banks, and the organ. The Cubs are in my blood,” he said

His dream of becoming the Cubs organist came about quickly. “I couldn’t hit a fastball so I knew had to do something different,” Pressy joked.

As someone that’s been with the organization day in and day out since 1987, the Cubs 2016 World Series victory is as good as it gets. “To get a World Series championship ring is the top highlight of your musical career,” he said.

One aspect that’s helped Pressy’s longevity is his consistency. Not in the sense of showing up to every home game, but his ability to perform songs that appeal to all generations.

“The library I play is large. I don’t have a sheet of paper that says you have to play A, B, C, and D. I try to mix my music to please everybody,” he said.

Pressy’s variety comes from a simple mantra, “don’t dominate one era of music, try to spread it apart.”

This also extends to his listening habits in his spare time. “I listen to XRT a lot, no joke! I also listen oldies, hard rock, and a lot of newer music. You have to listen to new music. Look at David Ross, he’s dancing to everything these days!” Pressy said.

Aside from playing songs familiar to fans 10 years old or 60 years old, Pressy thematically structures his music to align with whichever team is playing the Cubs. “When the Cincinnati Reds are in town I’ll play the Ohio State theme song or ‘Hang On Sloopy.’ Similarly when the Yankees were just here I played ‘Yankee Doodle Dandy.'”

His position in the Wrigley Field press box means Pressy is privy to getting inside access to the numerous celebrities that visit Wrigley Field.

His favorite? Bill Murray.

“His rendition of the seventh inning stretch as Daffy Duck during the World Series was one of the best things I’ve seen,” Pressy admitted.

Pressy’s most revealing tidbit came as a surprise though. “Seeing actors come here in is incredible, they’re in awe of singing the stretch in front of the fans and can be nervous,” he said.

Former Cubs players are also a treat to see. “People like Jose Cardenal, Jody Davis, and others are a lot of fun. We talk about their past time with the Cubs and how it’s changed.”

For Pressy, one of the highlights is interacting with Cubs fans. “You can’t stump Cubs fans,” he said. “I’ll get people that come up to me saying, ‘hey remember that game against Cincinnati in April where you played this song in the third inning?’ They remember more than what I play.”

Take a moment here to imagine Wrigley Field without ivy on the walls, the basket in the outfield, the bright red marquee in front. Pretty hard to do, right?

The sound of Gary Pressy’s organ is in that category. It’s a defining staple of the Wrigley experience for first-time visitors and fans seeing their 100th game.

Next time you’re at the ballpark, give a wave to Pressy up in the press box. You know he’ll be there. After all, he hasn’t missed a game since 1987.


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