Chicago: Going Native

Why is Chicago so like a long sausage in a soft bun? Just ask Craig Leffel, director of production of ONE at Optimus, and his dinner guests Dali and Freud

What is the best thing about working in advertising in Chicago?

The ad community here is pretty tightknit for a city of this size. I’ve worked here for over 20 years, and there’s a camaraderie within the creative community that’s rewarding to be a part of. There are a good number of agencies that we are fortunate to work with who consistently do good work for their clients. There’s an incredible work ethic too.

And the worst thing?

Winter. Wind. Horrible cold. And that there’s an incredible work ethic here.

What advice would you give to a visitor?

Get out into neighbourhoods. Don’t give more than a day to seeing Michigan Ave, Bean, the Loop, anything downtown really. You’ll find the real character and charm in Chicago out in the more ‘lived in’ areas of the city: Bucktown/Wicker Park, Ukrainian Village, Lincoln Square, Andersonville, Roscoe Village. The list goes on.                       

What is the best Chicago ad you have the seen in the last few months?

DDB Chicago’s 9/11 tribute spot for State Farm. All politics aside, it’s an emotionally resonant piece of film.

If you’re booking a hotel in Chicago, where would you choose to stay?

The James. Just enough pampering and cool factor to make you feel special along with a good location in River North.

If Chicago was a product, what would it be? 

A hot dog. It’s a collection of humble parts working together to create something truly world class when done right. No surprise it’s what we’re known for. 

What is Chicago’s favourite pastime? 

Obsessing over our sports teams, drinking beer, working hard, and being nice with a slightly sarcastic tone.

What do you miss when you are out of the city?

The food. Funnily enough, no matter where I am I always wonder if I couldn’t get the same thing or better back in Chicago. I’m usually right, as long as it’s not fresh seafood.

Who do you/would you love to work with in the industry?

I have always wanted to work with Muppets, Inc. It would be crazy fun to work with the people at [Adult Swim] or The Daily Show. The truth is, as an integrated production services company, we’ve already had the chance to work with some of the best people in the business at ad agencies and production companies. as I’m now running our production arm, I would love to keep all of those relationships going full tilt boogie, far into the future.

Where’s the best place to eat in Chicago?

Since it’s impossible to answer that question, I’ll tell you the best place to get a Sloppy Joe, which is almost as important: Tommy’s Guitars and Café near Humboldt Park. Tommy’s is a guitar shop, first and foremost. No mistaking that. They also operate as a little café, and their Sloppy Joe is probably the best in the city, if not the state.

The best place to drink?

We have over 2,000 options. A few of my favourites: Clark Street Ale House, Rossi’s, Hopleaf, Violet Hour, The Matchbox, Fernandez, Big Star, Clutch.

One dinner table, four places. You and who?

Salvador Dali. Freud. Plato.

What’s your one-line life philosophy?

Work hard to be lazy.

What’s your favourite memory of Chicago?

So far, it’s when the Blackhawks won the Stanley cup and the parade that followed. The outpouring of support and love from the city – downtown no less – was amazing to be a part of.

If you could say just one thing to God, what would it be?

Seriously? That’s my actual answer. I would just walk up and say ‘seriously?’.