Longtime Wrigley Field organist Gary Pressy reflects on more than 3 decades worth of Cubs memories

For the last 33 years, Gary Pressy has been a staple at Wrigley Field as his fingers danced across the keys of the ballpark’s organ. He was there for the Cubs’ first night game in 1988, and he was present for Game 6 of the National League Championship Series in 2016 when the Cubs clinched their first World Series berth since 1945.

But after all his years of service, Pressy, 61, has decided to take his final bow and will retire after this season.

Working as the organist at the Friendly Confines has been a dream come true for Pressy because it’s a combination of his two loves: The Cubs and music.

Growing up in the Ashburn neighborhood, Pressy was obsessed with the Cubs. One of his favorite teams, in fact, is the 1969 Cubs, though, he doesn’t like to think about the final two months of that season.

Pressy started playing the organ at an ice rink in Crestwood, Illinois. He got his break when then-White Sox organist Nancy Faust hooked him up with gigs at Bulls, Loyola and DePaul games.

Eventually, former Cubs executive John McDonough — who knew Pressy from the Chicago String — brought the organist to the Cubs. He played three games in 1986 before he was hired full-time the following season. If all goes as planned Sunday will be Pressy’s 2,687th consecutive game.

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Before what could be his final game behind the keys at Wrigley Field on Sunday, Pressy joined the Sun-Times for this week’s chat room and reflected on more than three decades worth of Cubs memories.

You’ve performed at nearly 2,700 Cubs games. Do you have a favorite?

Gary Pressy: “The one game I could say, and I think it’s pretty easy, was Game 6 of the NLCS in 2016 when we happened to clinch a spot to the World Series and we beat the Dodgers. ... I said, ‘Finally, after so many close calls like in ‘03, we were so close, we finally got to the World Series.’”

What’s your favorite song you play?

GP: ”I love the 1969 Cubs hit ‘Hey Hey Holy Mackerel.’ I still love that song. That’s the team I grew up with when I was a kid watching every Cubs game on TV with Jack Brickhouse and the ‘69 club had four-and-a-half good months of baseball and we won’t talk about the other half.”

Do you take requests?

GP: “Oh, yes. A lot of times the ushers will bring up a note. ‘Can you bring this song for me?’ And whatever, and I try to comply. If I know it, I’ll play it.”

Any odd requests?

GP: ”Well, they like, ‘My Kind of Town’ or ‘Sweet Home Chicago’. Nothing really out of [the ordinary.]”

Have you ever taunted an umpire or opposing player?

GP: ”There was one umpire, Bruce Froemming, who called up one day, and I said, ‘Uh-oh. What did I do wrong?’ And he says, ‘I love your music. My parents are celebrating their 60th anniversary and they’ll be behind home plate. Can you play ‘Let Me Call You Sweetheart?’ while I give them flowers?’ And I said, ‘Yes, I can.’

“But no, I’ll never [play] like ‘Three Blind Mice.’ I don’t do that garbage. That’s pretty stupid.”

Who has the best rendition of ‘Take Me Out to the Ballgame?’ And who has the worst?

GP: ”Definitely Vin Scully, the Dodgers broadcaster in 1998. He sang the stretch in April and ... I said he must’ve been Irish tenor — what a tremendous job he did.

“Now we have to flip the record, huh? Well, [laughs] Ozzy Osbourne was pretty ... different. Let me put it that way. I’ll tell you what, he got the notes correct, but I don’t know what the heck he was singing. He may have been singing it backwards.”

What’s one of your favorite memories on the job at Wrigley Field separate from games?

GP: ”I had the pleasure in 1988 on the Friday before the season ended to play ‘Hail to the Chief’ when President [Ronald] Reagan threw out a first pitch. I never thought I would hear that at a ballpark.”

You were here for the first night game at Wrigley Field in 1988, right?

GP: ”Yes I was. We had a rain delay, so geniusly, I played ‘Rainy Days and Mondays Always Get Me Down’ because it was on a Monday. So I did the first night game. ... It got rained out. And then I was here for the Mets, the official night game.”

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How did night games impact you?

GP: ”With everybody, it took time to get used to it. But I would say after two games it was like, ‘OK, we have a night game tonight? Let’s do it.’ No big deal.

“Wrigley Field is so traditional and I thank God I’m in a ballpark that has organ music and in a ballpark that’s so traditional. I could not have picked a better venue to perform my talents.”

Who’s your favorite Cubs player?

GP: ”I’ll tell you my top three. Ryne Sandberg, Mark Grace — I could keep going, really — Jody Davis. And I mean all these guys. I’ll tell you a great guy that I met in the press box here was Ben Zobrist. Could be one of the nicest persons. He asked if he could take a selfie with me. Woah. ... So Ben is a super, super person and a super player and so he’s top 3, 4 of all time.”

What’s the last thing you want to do as Wrigley Field’s organist?

GP: ”You know what really would be a send off? And I did this once and I would like to do it again is be at Grant Park on a stage in front of millions and playing the organ for the parade as the champs come in again. That’s what I want because I want to play ‘We are the Champions’ again.”

What’s next?

GP: “I’m going to spend a lot of quality time with my family. My mom, [Virginia], is 95 years old. She threw out a first pitch in 2016, and she told Justin Grimm who caught the ball that with the help from God, the Cubs are going to win the World Series. They did, and so now I’m throwing out the first pitch on Sunday and I better make sure that it’s just as good as mom’s.”