Chicago ConfidentialIt is difficult to get indignant at Chicago. —Jack Lait and Lee Mortimer

This month Chicago brings you our annual Best of Chicago issue (I definitely cosign on CHIRP and Downtown Sound). Having worked at the Reader and now Chicago, I always look forward to Best-Ofs, and similar issues. Not just because they’re fun to work on, both from the editorial and production sides, but because it’s captures the art and public commerce of the city—truth be told, a big reason people move to cities in the first place—at a specific time.

The specific "Best Of" newspaper/magazine concept seems to be relatively new, by which I mean in the past two or three decades (I could be wrong, given that that timeline coincides with how long I’ve been alive). But things like it exist in the annals of history. One of my favorites is the book Chicago Confidential*, by Chicago reporters-turned-New York Daily Mirror bigshots Jack Lait and Lee Mortimer, who also did versions for New York and D.C.

It was published in 1950, and probably seemed kind of dated even then, with its "hurly-burly, rough-and-tumble, guns-and-girls" neon noir sensibility. Not for nothing does it carry a blurb from Estes Kefauver, of the famous Kefauver Committee, who wrote that it contains "a tremendous amount of information." (Seriously, that’s his whole blurb.)

Indeed it does. Much of it is a history of the sordid sides of Chicago, and how not to get into trouble (or, if you read between the lines, how to get into it). But it also focuses on how to live like a swell in mid-century Chicago—how to get a good table, how to pick up women, where to drink—if you’re not yet a bigwig. And if you’ve got money, want a good time, but are new in town, it turns out that if you want to be a swell some things never change:

Clark Street (N-S) [100 W] Theatrical, at Randolph, thoroughly commercial in the Loop, bawdy north of the river.

Rush Street (N-S) [100 E] Deadfall lane, with the plushiest cocktail lounges, the most expensive broads. Once an avenue of fine and aristocratic homes, now sports a pizzeria, tavern, restaurant, or intime cabaret every ten feet. Show gals, models, and kepties live in the vicinity. (p. 297)

That Rush is now the heart of the Viagra Triangle probably just has to do with the aging of the American population. How do you meet these women? The male authors have plenty of atavistic advice.

Late-daters are the best. Let the other chump spend to take her dancing and get her loaded, after which she kisses him off and meets you elsewhere.

The ratio of eligible males to susceptible femmes is so much in your favor that you don’t have to spend to keep them happy. A gag is worth a gem. (p. 130)

Which probably has something to do with their advice for women:

Advice to young girls: do not come to Chicago in search of a career unless you have enough to support you for six months, return fare home, and strong will power. (p. 116)

Not all of Chicago Confidential is how to be a terrible person. Some of it is service journalism:

Artificial Eyes for Animals: We don’t know why you’d be interested in this, but put in just in case you are. Dorothy Flicek, 1151 W. Grand, HA 1-1339

Railroad Cars, Used: Just why you want to buy a second-hand railroad car is beyond us, but if you do, Briggs and Turivas, CO 4-1420, will be glad to supply you.

Worrier, Professional: While you’re waiting for the results [of your venereal test], call Frank Teurfs, HA 7-3994, or James Salach, BE 5-1867, who will do your worrying for a fee.

(Not joking: yesterday I was driving to Munster, spotted a gutted Metra car, and thought "that would make a nice small house." And come to think of it, I would make an excellent professional worrier. In some ways, I was born too late.)

And some of it is just the usual expats looking down at the rubes:

Home-grown big shots never mean as much as the imported variety. The autograph nuts wouldn’t cross the street for the signature of Chicago’s most famous, but a Hollywood bit-player is worth standing in the rain for. Anyway, Chicago is painfully short of local celebrities. Those who fancy the favored must depend on transients from New York or Los Angeles between trains.

Native VIPs who can afford the flossy resorts are mostly gamblers and gangsters, or well-heeled merchants and their fraus or sweeties. The real bluebloods seldom patronize public dining or dancing establishments. These people entertain and are entertained in their homes or private clubs.

The glamour joints are thus forced to exist on the pickings from mobocracy and slobocracy. (p. 224)

Whereas well-dressed Eastern men never have creases in their sleeves, the Chicagoan considers it necessary to show that he has had his suit pressed. Well, what did you send it to the tailor for? (p. 279)

And, of course, everyone looks down on our neighbor to the west:

An overwhelming majority of [Cook] County residents are fine family folk. The people are as respectable as any anywhere. But some towns right beyond the Chicago confines are carnivals of crime and lewdness, outdoing the worst in Chicago at its worst. There is, on first thought, Cicero. (p. 106)

An attitude that was not without its hypocrisy:

It is difficult to get indignant at Chicago. So much is so open, and law-breaking is so obvious that it comes to appear normal. There are thousands of dives running so flagrantly that they would mean jail for everybody connected with them if they operated an hour in New York, which is no Sunday school settlement. One gets used to it. (p. 78)


* I have the same lurid pulp version pictured. On the back is a B-girl, a bookie, a guy pulling a gun… and the lions in front of the Art Institute, because, of course.