The Red Underwear Story: How Crimson Briefs Propelled My Career as an Addy Winner

By Walt Jaschek

Part 1: A Surreal Night for an Addy Newcomer.

I’m heading to the St. Louis Addy Awards at Busch Stadium tonight, to cheer on the nominees, be inspired by the work, and see old friends. It’s with no small bit of nostalgia that I realize I have been attending the St. Louis Ad Club’s annual awards show, on and off, for exactly 30 years.

And though I’ve won my share of Addys over the years, none of them can compare to that first night, in 1989, when I won not one but two “Best of Show” Addys at Powell Symphony Hall. It was a mind-boggling night for which my 33-year-old self was not prepared. I was also not prepared for the article by Jerry Berger that appeared in the St. Louis Post-Dispatch the next morning. 

Here’s a clip of the piece, which everybody from my Mom to my dentist saw. (Back then, everybody read the paper.)

Finding this article again recently, I was reminded: 1,400 guests! No wonder I was a deer in the headlights!

Part 2: Looking Back at 1989 from 2019 (Video and Interview.)

A few weeks ago, the St. Louis Ad Club, to promote the 2019 St. Louis Addy Awards, asked members for “unusual Addy memories” they could capture on video and post on social media. I was happy to recall that first, surreal win, and how it led to what became known as “The Red Underwear Story.” Here’s the Club’s 60-second cut-down of a half-hour interview, taped and edited by Halski Studio. (It’s at the top of this piece.)

Q: Let’s get warmed up. Tell us a little about yourself. Name, title, where you work, a quick journey through your life in the ad business.

Walt: I’m Walt Jaschek, freelance copywriter and creative strategist, and because Jaschek is impossible to spell or pronounce, I DBA as Walt Now, as in, “What Now? Walt Now!” I have been so blissfully self-employed since 1988, and if you do the math, that means more than 30 years. So don’t do the math. 

Q: What’s the difference between a copywriter and creative strategist?

Walt: Pants. Copywriters wear jeans. Creative strategists wear khakis. So today I come to you as a copywriter. But I have some khakis handy.

Q: What’s your perspective on the focus on winning awards in the advertising business?

Walt: Well, I think there are three reasons they are the big dang deal that they are. (1) We work mostly in anonymity – if you write an article or draw a New Yorker cover, you get a byline. They don’t put bylines on ads, though God knows I’ve tried. It’s a way of saying, “Look. I did this. Me. Do you like it?” (2.) Agencies know awards represent a creative culture, and culture attracts talent. And (3.) let’s cut to the chase: ego. Creatives are a roller –coaster of insecurity and egomania. I mean, would I carry this award around with me if I had more self-esteem?

Q: What about the Addys specifically? How does an awards show that is geared towards the local level different than national shows?

Walt: The appetizers are better. Here in St. Louis, you’re far more likely to see toasted ravioli and gooey butter cake. You’re not gonna get THAT at Cannes. No, seriously, I think it’s a matter of building community. Of representing. Saying, “Look at the work coming out of St. Louis. Take that… Austin.” Or to keep it in the district: “Check it out… Des Moines.”

Q. Do you remember your first Addy?

Walt: Sure. You always remember your first.

Q. Do you remember how many Addys you’ve attended?

Walt: No. I’d have to count the hang-overs.

Q. Is there a specific Addy story you’d like to share with us today?

Walt: I won my first “Best of Show” Addy in 1988 when I was 33 years old, my very first year of freelancing, for the ONE and ONLY THING I submitted that year: a one-page piece of a paper — a funny letter announcing my business launch. Unprepared, I had to go on stage at Powell in front of a huge crowd to accept the award from comedian John Byner, and pictures of me from the podium have a shocked, deer-in-headlights quality. I improvised something about being glad I wore my “lucky red underwear.” That was too much information, now and then. 

Q. But the red underwear thing became a running joke, right?

A. Right. That line became a running joke, and at another Addy ceremony years later, when I teamed up with Paul Fey and won a “Best of Show” for radio, we actually brought red underwear up to the podium and threw them into the audience. People were grabbing at them, like Fred Bird throwing t-shirts at Busch Stadium. For years after, people would say to me in public: “I still have your underwear!” Depending on who I might be with, that could be a little disconcerting.

Q: What lesson can we take away from your Addy story?

Walt: My quite serious take-away from that silly story is this: Enter SOMETHING. Even if it’s it’s only ONE thing. And even … if it’s the ONLY thing you got!

Q. What piece of advice would you give to anyone considering entering the St. Louis Addys this year?

Walt: iBuprofen. Take it early And often. Also: have a speech prepared. Just in case. Otherwise, you could end up unprepared. Like me.  (Lifts award with red underwear draped on it.)

Q. Thanks, Walt.

Walt: See you at the show!

Writer Walt Jaschek is a 2018 inductee into the St. Louis Media Hall of Fame.

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