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David Letterman and Chicago: The top 10 turning points

For years, David Letterman’s CBS talk show began each night declaring its origins in “the greatest city in the world”: New York, where the host stayed put over three series in three different time slots on two different networks.

But the devoted Hoosier also had a soft spot for Chicago, the metropolis he used to visit during his boyhood in Indianapolis.

“I have pleasant, deeply rooted memories of my visits to Chicago,” Letterman told the Sun-Times in 1989. “My father and I flew up on an Eastern Airlines DC-3, and to me, the whole thing was just magic. You’re 10 years old, and you’ve never flown before. I remember we hung around the Palmer House for a trade show.”

Decades later, on national TV, he retained that respect, and at times entire sequences were built around the city and its prominent citizens. As Letterman approaches his final “Late Show” on Wednesday, here are some of the great Chicago tie-ins during his 33 years on late-night TV. Let’s just pull a number out of the air and say 10.

1. The Chicago Theatre shows

As NBC’s “Late Night” host, he had taken the show to Burbank and to Las Vegas, and for his next field trip Letterman set up shop at the Chicago Theatre. Over four nights in 1989, he asked Michael Jordan about his tongue, held the ball for Bears kicker Kevin Butler and accepted a manhole cover from Mayor Richard M. Daley. Buddy Guy and James Cotton jammed with the band all week, and a replica L car navigated the tracks overhead.

Two guests were notable for what was yet to come. Jay Leno, Letterman’s favorite sparring partner in those days, had another dazzling round of banter, the kind we’ve missed since Leno’s “Tonight Show” ascension cleaved their chemistry. And Oprah Winfrey had such an awkward exchange with Letterman that she silently vowed to avoid ever having another. More on that later.

2. The Steppenwolf show

Fans display their tickets to the Steppenwolf show in 1996. | Sun-Times Files

Fans display Steppenwolf tickets. | Sun-Times

Letterman had defected to CBS by the time he next brought his show to Chicago, for a single night in November 1996. It was the height of Rodmania, and the Bulls bad boy took Letterman on a Chicago tour that culminated in both buying and wearing dresses at Marshall Field’s. Guests on the storied Halsted Street stage included Anthony Edwards, Natalie Cole and a bunch of pets from the ‘burbs doing stupid tricks.

3.  Chicago night at the Ed Sullivan Theater

"Late Show" fans line up at Midway Airport for their trip to New York in 1998. } Sun-Times Files

“Late Show” fans line up at Midway Airport for their trip to New York in 1998. | Sun-Times

By April 1998, Letterman was sick of traveling to his fans, so he brought the fans to him. Three planeloads of Chicagoans were flown to New York to watch an episode devoted to Windy City weirdness. Boos greeted lead guest Jerry Springer (back when he still was based at NBC Tower) and a taped piece showed “Late Show” staffer trying (in vain) to penetrate Harpo Studios. A bluesy Top 10 was a highlight — even though it starred a musician from Massachusetts, Taj Mahal.

4. Dave vs. Oprah

Though she never set foot on Letterman’s shows throughout the ’90s and early 2000s, Oprah Winfrey was always a looming presence. Sensing the Chicago daytime talk powerhouse had soured on him, Letterman reacted by making her a frequent punchline. He goofed on her weight and her magazine, and he brought out two droll stagehands to act out transcripts from her show. The running gag took a wistful turn in 2001 when Letterman started campaigning to be on Winfrey’s show or host her on his for a “Super Bowl of Love.”

Jay Leno, Oprah Winfrey and David Letterman appear in a "Late Show" ad during Super Bowl 2010. | CBS

Jay Leno, Oprah Winfrey and David Letterman appear in a “Late Show” ad during Super Bowl 2010. | CBS

Eventually, Winfrey thawed, breaking the ice by sending Letterman a tub of children’s books when his son Harry was born in 2003. Two years later, she succumbed and appeared on “Late Show” — just in time to hype the Broadway opening of her musical “The Color Purple” across the street. Since then she’s been Letterman’s obedient ally, appearing in Super Bowl ads for his show in 2007 and 2010 and journeying to Muncie, Ind., to appear with him at his alma mater, Ball State University.

The feud’s origins finally became clear when Letterman appeared on “Oprah’s Next Chapter” and Winfrey pointed back to that 1989 Chicago Theatre chat. “It was a terrible experience for me,” she said. “The guy in the audience started yelling, ‘Get her, Dave!’ You were sort of baiting the audience, and there were a bunch of drunk guys down the front. I was trying to like, you know, mitigate the whole thing, and it felt so uncomfortable to me. I didn’t want to have that experience again. That’s really all it was for me.” Letterman said he didn’t remember the moment but added, “I’m sorry. I’m very sorry.”

5. The Phil Donahue Countdown Calendar

Phil Donahue

Phil Donahue

For a decade Donahue originated his daytime talk show from Chicago, but what caught Letterman’s interest was when it was leaving. After Mr. “Is the Caller There?” announced the show’s transplant to New York in 1984, Letterman anticipated his arrival by ticking off days on calendars that started out huge and got huger. One night, Donahue himself stepped out to wordlessly do the marking.

6. Kid scientists

Spun off from the “Late Night” demos by Naperville teacher Lee Marek, these segments feature his young students showing Letterman experiments with a little educational value and a lot of fire and noise. The host never seemed to learn the city isn’t called “Napierville.”

7. Rod Blagojevich

Rod Blagojevich chats with David Letterman in 2009. | CBS

Rod Blagojevich chats with David Letterman in 2009. | CBS

Two months after his arrest on corruption charges, the ousted Illinois governor took a grilling from one of his most scorching roasters. In the classic sound bite, Letterman responds to Blago’s comments about “wanting to be on your show in the worst way” with, “Well, you’re on in the worst way, believe me.”

8. Eye popping

In 2006, Chicago’s Kim Goodman astonishes America with one of the more dramatic Stupid Human Tricks: popping her eyeballs almost half an inch out of their sockets.

9. The Kankakee gazebos

When the Places Rated Almanac named Kankakee the nation’s worst place to live in 1999, Letterman couldn’t stand to see a Midwestern city suffer. First he sent the gift of a gazebo. Then he sent another gazebo and proposed the downstate community market itself as the home of the twin gazebos. Sixteen years later, as Letterman prepared to retire, Kankakee high school students refashioned one of the gazebos into a rocking chair and presented it to a Letterman rep in a ceremony aired on the show.

10. Bill Murray

Bill Murray customizes Letterman's desk on the first "Late Show" in 1993. | CBS

Bill Murray customizes Letterman’s desk on the first “Late Show” in 1993. | CBS

Though he shuns most talk shows, the funny man from Wilmette is a dedicated Dave devotee, often augmenting his appearances with costumes and elaborate bits. He was the first guest on Letterman’s NBC show and his CBS show, and his “Late Show” swan song is scheduled for Tuesday.