the windy city is mighty pretty


I might say I don’t like to repeat myself on this blog, but a quick search proves that to be delusional, so I must cop to something: today being Oprah’s last taping, I’m going to retell the story of The Day I Was on the Oprah Winfrey Show. Along with an addendum. Anyway…

It’s April 1994, and I’m 26 years old and just getting back from the usual afternoon game of hoops at the Lodge. The phone rings and it’s the lady in charge of booking at the Oprah Winfrey Show – she says they’re doing a whole hour on the movie “Reality Bites,” there’s going to be some “stars” there, and they want me – as Official Spokesman of Generation X – to be on the show.

The year previous, we’d put out the 13th-GEN book, and that particular month I was one of sixteen writers that had put together Next: Young American Writers on the New Generation. The anthology didn’t sell that well, but it was on President Clinton’s booklist, and we had all sorts of great parties when it came out.

So I said yes, and two weeks later they flew me to Chicago and put me up in a swanky hotel. By airtime, it became clear that this show was no longer going to be about “Reality Bites” nor was it going to have Ethan Hawke or Winona Ryder as guests: it was going to be a Baby Boomers vs. Generation X slugfest and whomever had the most snark was destined to win.

The Oprah show, at that point, had two “green rooms” – in one, they stuck a bunch of Baby Boomers in their 40s, and in our dressing room, we had a cool chick from an indie bookstore in Atlanta, a wonderful 25-year-old schoolteacher from Missouri (hello, Melanie Finnell!), a 26-year-old junior exec at American Airlines, a very shy girl that ditched college to be a kayak instructor, and me.

Nervous as hell, we all began to blather at each other, and in the hour leading up to the show, had the best “generational” discussion I’ve ever had – honest, heartbreaking, funny, and precisely the sort of thing that should have taken place in front of the cameras. Obviously, they were keeping us separate from the Boomers so that the fireworks would happen on stage, but the strategy backfired.

The show starts, and those not on stage watched the action on the monitor in the green room. First up: the American Airlines guy had to go head-to-head with some lady who had been in an email war with him for months. Next, the indie bookstore chick had to justify her existence to a “self-made millionaire” in his late 40s whose only expertise seemed to be getting Reagan-era economic facts completely wrong.

Then came the schoolteacher who said she didn’t want to be a schoolteacher anymore, with a round of opprobrium from the audience. Worse yet, the shy kayak instructor basically got booed out of the studio for not “getting a real job.” Leading the charge were two African-American women in the front row, who said their lives had been fraught with hardship, and that all whiny Generation Xers should probably kill themselves and save America the trouble.

I mean, how do you complain about your rotten job, lack of real romance, and pervading depression when there are two ladies who “clean toilets in Toledo” every time you say anything? You can’t, actually.

Finally, they called me out to the stage, along with Susan Mitchell, who edited “The Boomer Report.” All I could think was, “thank God they mentioned my book.” Oprah’s head was very, very large. The lights were amazingly intense, the audience surrounds you like a Roman gladiator amphitheater, and the whole energy of the place is positively nerve-fraying. The last thing the producer tells you before you go on stage is, “You are about to be seen by 10 million people in 43 countries.” I wanted my mommy.

no, you’re right – that haircut was ghastly even in 1994

I was hoping that the argument would turn into something intelligent now that us “experts” were on stage – remember, this was days after Kurt Cobain’s suicide – but it only got worse. More name-calling between audience members, silly irrelevant stories about young hardship, sprinkled with a few confusing statistics to keep things misleadingly sociological. Half-baked tangents were swirling around me, the audience was getting riled up, I felt my hair start to get large, the lights pounded… when suddenly Oprah turns to me and says “Ian.” My stomach tightened. “What do you think about all of this?”

And for a split second, I’ve never had less to say in my life. In a mad rush, my brain wanted to say “I think this is the most pathetic argument I’ve ever eavesdropped on in my life,” but I managed to tell them a nice paragraph full of bullshit. Basically that the two generations can’t play tit-for-tat because it’s an argument that nobody ever wins. And that dreams are not transferable across eras – what causes me great pain may seem like a luxury to you, but I still feel pain nonetheless. And that it’s okay to be a kayak instructor.

Oprah said, “I don’t really get what you mean,” then cut to the last commercial. And that was it. There were 40 seconds left in the show, they started playing that Oprah “time’s up” music, and I couldn’t believe it. Oprah herself wondered aloud if they had accomplished anything, and I got the feeling it had been one of their worst, most pointless shows. I buried my head in my hands.

They unhooked the mike from my flannel shirt and I wandered off the stage in a daze, very angry, very confused and wondering why they would ship us across America to embarrass us like that in front of 43 other countries. And as us Gen Xers wandered out of the studio together into the cold Chicago wind, we saw the Boomers – including the women who had “cleaned toilets in Toledo” – all drive off in a limo together. The ladies had been a plant.

So we spent the rest of the day walking around downtown Chicago. We felt like we’d been used, like we’d been reduced to the same idiots who sit in those very chairs on stage in years past, the transvestite mothers who eat their children. We’d sold our private moments to Oprah for a chance to suckle at the great giant teat of the American underbelly, and we were all horrified.

Four hours later, we were still doing tequila shots at the hotel bar.


I should mention a few things here. First off, this was just weeks before the “secret gay crush” episode of erstwhile-Oprah-rival Jenny Jones led to a murder and a general soul-searching of daytime tabloid television. Oprah herself seemed genuinely nice, and I don’t think it’s an accident she started dedicating her shows to Dr. Phil-twinged self-empowerment soon thereafter. She evolved, and that’s how she managed to stay so umbilically-connected with normal Americans for so many decades.

The other thing is this: after seeing myself on television, I realized I should never be on any kind of film or video ever again. I was so chagrined at the way I looked that I awoke from wisdom tooth surgery two weeks later, convinced that Oprah had turned me into a frog with gelatinous gills. It took my mom 2 hours to talk me down from my post-op nightmare haze.

Which is fine. A man’s gotta know his limitations. There’s also the story of how my Oprah episode was pre-empted by Fat Teen Week for everyone not in the Mountain Time Zone, but there’s only so much self-plagiarism I can muster before I start feeling like an old farting uncle who keeps repeating the same stories until he’s eventually just left in the car for the holidays.

0 thoughts on “the windy city is mighty pretty

  1. litlnemo

    I thought you looked fine on tv, for what it’s worth.
    And I’m glad to hear this story again. I had forgotten about the women from Toledo.

  2. Bud

    I’d like to see this….
    I re-read Generations recently and the predicted Baby Boom vs GenX “war” doesn’t seem to me to have been nearly as big a deal as Stauss & Howe predicted. Ditto our alienation and hardships. And the predicted Boom tendency to forgo material reward in return for moral authority.
    Maybe the huge role of new technology (which surely gives GenX an unexpected edge), and globalization, have changed the script.
    What’s your take, Ian? And do you ever talk to Neil Howe? It’d be interesting to hear his take on the last twenty years….

  3. John

    I agree with Bud. Now that Gen Xers are entering (or firmly ensconced) in our 40s, what’s changed with us? Do we look at the Millennials with the same disdain that the Boomers used on us? What’s your take on it, Ian? Write another book about it! (Seriously)
    I live on the Lower East Side, and frequently have to pass scores of barhopping twentysomethings on my way home at night. And yes, I do look at them with a mixture of disdain and envy: Disdain that I think they’re wasting their youth; envy that there’s a relaxed attitude toward sexuality that we missed out on because we were bombarded with warnings about AIDS, date rape and sexual harassment (and justifiably so). Or maybe I just missed out on it. But there’s also some wisdom and gratitude there – wisdom that I’ve learned what I’ve learned since then; gratitude that I don’t have to go through it again. And then I smirk because I know that in ten years they’ll all have guts and thinning hair and bum knees and be thinking the same things I am now.
    I don’t know. The older I get the more I believe that every generation goes through the same damn things at the same damn time, and always looks back on the upcoming one with that same mix of disdain and envy and, ultimately, wisdom. Hey you kids! Stop playing your rock-and/or-roll and get off my stoop!

  4. josie

    I love this post too; But I feel short-changed. I need to see the video. These days, you can’t get away with talking about something like this without showing us video. :)

  5. Didu

    You must have been on Oprah during our, “where did Ian ever end up” period. So glad facebook reunited us and so glad you told this story again although for me, it’s the first time. Love it. Wish I’d seen it. You were perfect.


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