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Swinging one leg and the rest of his body out over thousands of Wrigley Field fans while nervous handlers in the broadcast booth gasped, actor Cuba Gooding Jr. howled “Take Me Out to the Ball Game” with abandon before revving up the crowd further with a rousing, “CUBBIES, SHOW ME THE RUNS!!!”

Gooding served as that 1999 day’s seventh-inning stretch “guest conductor” while in town promoting his new movie, “Instinct,” a few years after he won the best supporting actor Oscar for “Jerry Maguire.” As he made his way along the catwalk to watch the end of the game from a skybox, the actor basked in fans’ cheers and chants of his “Jerry Maguire” catchphrase “Show me the money!” before flinging his baseball cap into the grandstands.

Taking his seat at last, Gooding grinned and cackled, “I am trapped right now in ‘Ferris Bueller’s Day Off.'”

That an Oscar-winning actor’s reference point for his Wrigley Field experience would be a 1986 John Hughes movie says much about the ballpark’s prominence in popular culture. Wrigley Field, which celebrates its 100th birthday April 23, may be most famous for the sporting events it has hosted, but it has far transcended that function in the greater world.

It’s worth noting that tickets remain available for the New York Yankees’ May visit to Wrigley, but fellow New Yorker Billy Joel’s July 18 concert there is sold out. Aside from hosting a few large-scale music events each summer since Jimmy Buffett first headlined there in 2005, Wrigley Field has been leading separate lives on film, on stage and in other media.

“People feel like it stands for something,” said Stuart Shea, author of the newly published “Wrigley Field: The Long Life & Contentious Times of the Friendly Confines” (The University of Chicago Press). “And I think it does stand for something. I think it stands for the way we romanticize the past.”

There’s a reason that the most memorable image of the romantic montage in the original 1986 “About Last Night…” was Rob Lowe’s Danny taking Demi Moore’s Debbie up to a rooftop outside Wrigley Field to take in a game. Back then a rooftop was just a rooftop, a natural part of the neighborhood and not some bleacher-filled, beer-sponsored business, and the ballpark was less commercialized as well.

“We were just looking for stuff that set Chicago apart, that this was so cool to live in a city where you could do that at Wrigley Field and go to a rooftop,” said Tim Kazurinsky, who co-wrote the “About Last Night…” screenplay. “It was an old-fashioned type of thing then, before it all got renovated and they put lights in. On the other hand, Demi Moore’s body has probably gone through more alterations and renovations and changes than Wrigley Field at this point.”

Shea writes that the park’s connection to entertainment started early on, as owner Charles Weeghman, impressed by the postgame “hippodroming” at the Pittsburgh Pirates’ Forbes Field, began booking vaudeville shows to take place while the Chicago Whales of the Federal League were away from the then-named Weeghman Park. (After the Federal League folded in late 1915, the Cubs began playing there the following year.) The owner even installed lights on the field to illuminate Slivers, the famous baseball comedian who starred in the first July 1915 show, and acts with such names as the Five Juggling Normans and the Six Royal Hussars.

“People who lived in the neighborhood would come,” Shea said. “The idea of having nighttime entertainment in the neighborhood was appealing.”

But Bill Wrigley, who took control of the park in late 1918, wasn’t so interested in presenting live entertainment, Shea said, so the shows disappeared even as the sporting attractions diversified (including the Harlem Globetrotters and professional wrestling). Still, Wrigley Field had cultural impact in other ways. In 1941 it became the first major league ballpark to feature organ music, spurring other clubs to copy this move, Shea writes.

“They were also the first to broadcast their games on a regular basis,” Shea said, noting that home games were broadcast from the park, while road games were re-created via ticker tape. “Most baseball owners were terrified of radio, whereas Wrigley, an advertising man, saw the value of getting the word out.”

Although Buffett ushered in Wrigley’s new era of live entertainment, musical acts did perform there before 2005. The groups Sister Sledge and KC and the Sunshine Band participated in ’70s Night game promotions, and the rock-soul cover band Mickey and the Memories played at a July 1988 Cubs Care benefit that also tested the ballpark’s new lights two weeks before the first night game, Shea writes.

Shea said that when Chicago’s Big Twist and the Mellow Fellows performed between games of a doubleheader, “I remember (Cubs TV announcer) Harry Caray trying to come up with a term for them, and he called it ‘toe-rockin’ music.'”

A musician more famously associated with Wrigley Field was Chicago folk singer-songwriter Steve Goodman, who in the early 1980s debuted a new song, “A Dying Cub Fan’s Last Request,” on Roy Leonard’s WGN-AM radio show.

“Steve just said, ‘I’ve got a song that I think Cubs fans will appreciate,’ and he sang the song,” Leonard recalled. “Well, phones went off the hook. It was unbelievable.”

The blackly comic folk ballad details fans’ hopes being perpetually crushed “like so many paper beer cups” on the team’s “ivy-covered burial ground” before he envisions his own ashes being blown over the left field wall past the bleacher bums before coming “to my final resting place, out on Waveland Avenue.” That Goodman had been battling leukemia went unmentioned.

The Cubs didn’t like that song much, so, as Tribune columnist Eric Zorn reported, the WGN Radio program director commissioned Goodman to write a more upbeat one to serve as the broadcasts’ opening theme. The result was “Go, Cubs, Go,” which debuted on opening day 1984 and gained in popularity as the team reached the playoffs for the first time since 1945. A few days before the team clinched the division title, Goodman died, on Sept. 20, at age 36; he thus missed the Cubs’ heartbreaking elimination by the San Diego Padres after the North Siders won the first two games. A few years later some of his ashes were scattered over the Wrigley outfield.

Although “Go, Cubs, Go” eventually was replaced as the theme song, since 2007 it has been played over the loudspeakers after each Cubs victory, becoming a singalong in the stands. Perhaps it says something about Cubs fans’ confidence level that they would sing “The Cubs are gonna to win today” only after the team already has won.

Eddie Vedder, the Pearl Jam singer who grew up partially in Evanston, debuted his own Cubs song, the shanty-style “All the Way,” in 2007 and released a recording in 2008. Sample lyric: “When you’re born in Chicago you’re blessed and you’re healed/ The first time you walk into Wrigley Field.” Last July, Vedder became part of the Wrigley lore as a fierce thunderstorm rolled into the North Side seven songs into Pearl Jam’s set there, prompting the stands’ evacuation and a two-hour rain delay. The city’s curfew waived, the Seattle band rocked until 2 a.m., previewing songs from its new, appropriately named album, “Lightning Bolt.”

The ballpark also inspired one of Chicago’s most enduring homegrown plays, “Bleacher Bums,” which takes place in the Wrigley Field bleachers and premiered Aug. 2, 1977, in an Organic Theater Company production conceived by and co-starring Joe Mantegna and directed by Stuart Gordon. Dennis Franz also starred in the original production, while Dennis Farina, George Wendt and Gary Sandy would join later casts. In a defeat-the-point sort of way, a movie version that premiered at the Chicago International Film Festival in 2001 and played on Showtime the following year had to rename Wrigley Field as Lakeview Park and the Cubs as the Bruins due to a licensing dispute.

Though the 1949 comedy “It Happens Every Spring” was shot in part at a Los Angeles replica of Wrigley Field, and the Wrigley scenes from “The Natural” (1984) were filmed in Buffalo, the ballpark has been featured prominently on screen elsewhere. It was a key setting in “The Blues Brothers” (1980, as the cops and Nazis converge there after Dan Aykroyd’s Elwood lists his home address as 1060 W. Addison), “A League of Their Own” (1992), “The Babe” (1992, with John Goodman dramatizing Babe Ruth’s “called shot” in the park), “Rookie of the Year” (1993) and “The Break-Up” (2006), as well as “Ferris Bueller’s Day Off” (with “Save Ferris” on the marquee, and the title character catching a foul ball inside), “About Last Night…” and many TV shows.

As the cultural give-and-take goes, actors and other project-promoting celebrities, from A-list to D-list, now make a pilgrimage to Wrigley Field to sing, and often butcher, the seventh-inning stretch. This is useful because Cubs fans can take a break from debating the worst-ever Cubs team (will this be the year?) to arguing whether Mike Ditka’s breathless, pitch-and-rhythm-challenged “Take Me Out to the Ball Game” was worse than Ozzy Osbourne’s mumble slur.

Osbourne apparently was not reliving “Ferris Bueller’s Day Off.”

Use #Wrigley100 to share your Wrigley Field memories with us on social media.

mcaro@tribune.com

Twitter @MarkCaro