I started managing the classifieds section just days after I started working at the Reader, in fall of 2019. I was the new administrative assistant, so I was doing things like checking the mail, making coffee, and ordering office supplies—all of that fun stuff. But I quickly got the sense that, for some reason, covering classifieds was seen as the true grunt work of the office.
My boss told me I’d be running the section, and of course I nodded along, eager to impress and not so eager to admit that as a fresh 22-year-old, I’m embarrassed to say, I wasn’t quite sure what classifieds were. But I caught on quickly, learning the less-than-smooth process that had changed hands a few times just before I started: answer repetitive e-mails, field phone calls, pick up the occasional fax, and dump it all into a Google doc to prepare it for publication. I could tell from coworkers’ jokes and my predecessor’s lack of grief in handing off the responsibilities that working the classifieds section was something of a rite of passage at the Reader. There was a general attitude that the newbie covers it for a few months until positions shift.
And who was I to complain? I was fresh out of college and new to the city, and once I got it down to a science, I didn’t mind the work of placing ads. I didn’t mind that it was a little tedious, and I was able to suck it up and push through my younger-than-millennial-but-
older-than-Gen-Z hatred for making and answering phone calls.
But here I am, almost hitting my two-year mark of working at the Reader, and the section is still all mine. I won’t lie and say that running classifieds is my favorite part of my job, but it’s a part of my daily routine, and I’ve found moments of excitement along the way.
There are kind people who I interact with almost every day. I’ve gotten to play a key role in automating the classifieds process with our new website, to make it easier than ever for people to place classifieds. But the most exciting part about managing Reader classifieds has been learning about the history of the section, and its evolution from its 70s inception, to its glory days in the 80s, 90s, and 00s, to its steady decline as Internet ads exploded in popularity, to its present as a beloved but humble page or two of local advertisements.
A history of Reader classifieds
The first issue of the Reader, published in October 1971, had one page of classifieds. It was a spaced-out list of four categories—For Sale, Personals, Services, and Wanted—loudly sponsored by ABC’s WLS Radio 890.
“It was said the owners and earliest Reader employees would copy postings down from billboards in lakefront-area grocery stores and run them as classified ads in the next week’s paper,” remembers David Jones, who was hired as the Reader art department’s production assistant in 1976, and shortly thereafter became production director.
Of course, by the fifth anniversary of the paper, when Jones started, there was no need for anyone to hunt down ad content for the classifieds section. The October 1, 1976, issue includes ads for Notices, Rides, Help Wanted, Personals, Pets, Services, Housing, Vehicles, For Sale, Wanted, and Instruction, spanning a full 20 pages, including some comics and display ads. That said, 20 pages is still nothing compared to the following decades; longtime Reader readers will remember the sheer volume of the paper in the 80s and 90s, with the classifieds section existing as one of four massive standalone sections in the weekly publication. Still, by 1976, it was far from a one-person operation, the way it mostly is today.
In fact, it was such a collegial group effort to put the classifieds out each week that that’s mostly what Jones remembers from back in the day. He described the process to me in an e-mail—since I’m over here googling “galleys” and typesetting practices, I’ll just let him explain it:
“Every Wednesday morning—with press deadline falling Wednesday/Thursday night—the classifieds galleys would arrive from our typesetting office at Herringshaw-Smith on West Washington St., tightly scrolled strips of 11-pica-wide typeset photo paper that we’d lay out on worktables in shorter strips cut by category (Housing, For Sale, Help Wanted, etc.) shortly after we’d fired up the coffee pot.
“Classifieds director Mary Jo Madden and her small staff of ad-takers would have the galleys pre-headed with those general categories sent over to Herringshaw on Tuesday evenings, but then virtually everyone else in the company (production, editorial, and advertising staffers) would be packing in first thing the next morning to cut and sort those galleys to run through the Schaefer Coater hot wax machine, to be pasted by hand into appropriate sections of the classifieds pages. Production would do most of the paste-up, but editorial staff (often including founding publisher Bob Roth, and eventual publisher Jane Levine, from advertising—gifted eyes, both) would sit and proof the paste-ups, looking through the long gray stream of tiny agate type for minuscule typos and mis-sorts.
“Errors in the paste-up pages would then be fixed with X-Acto knives and Scotch tape, most notably by ad director Tom Yoder, who was known for his skills cutting and repairing galley errors with his Swiss Army knife, tucked ever handy in a khaki pants pocket along with his trusty pocket watch. Two most important tools for that task—a sharp, ready knife and a keen sense of time.”
(Maybe others get waves of nostalgia hearing about such processes? I learned something new today.)
Vera Videnovich also described this foreign printing process to me. She was hired at the Reader in 1990 as a part-time classifieds rep. Backed by a typing test and a reference from an SAIC college professor, she was later promoted to part-time classifieds shift manager (That’s when she became the boss of current Reader theater and dance editor Kerry Reid, who worked part-time from 1992-1993 writing and renewing ads) and eventually started typesetting for the editorial department.
She wrote, “I picked up a shift in editorial typesetting in the days before many writers had PCs, Internet connections, or even floppy discs to hand in copy to their editors. I’d type anywhere from 1/2 to 1/3 of the entire editorial copy—when the paper was in four large sections. This included typing in classified ads that had a weekly revenue total that was more than I made in a year working that classifieds shift.”
Overlapping with Vera Videnovich was Monica Brown, a receptionist at the Reader from the time she moved to Chicago in 1992 until 2008. An artist by trade living in Wicker Park (“back when it was very Bohemian”), Brown fielded classifieds inquiries in person, over the phone, via mail, and with the then-new e-mail and voicemail systems. She looks back fondly on her Reader days, noting that many people worked part-time and were encouraged to be creative and follow passions outside of work. Like so many other Chicagoans, she got to know the city through the paper. Her first visual art exhibitions even ran in the Reader listings.
Not only was I fascinated to hear about Videnovich and Brown’s roles at the time, but I also enjoyed discovering some similarities between us. Brown and I both learned the city from inside the Reader. Videnovich and I both started at the Reader at age 22, working in classifieds. She also recalled, “When I was first hired, I asked if there was a dress code. Pat Davis (a great and patient classifieds manager) pointed to a man dressed in Hawaiian shirt, shorts, flip flops, and a ponytail. It was Bob Roth, one of the owners. It was clear there was no dress code.” That same thing happened to me, except it was my coworker Teddy Piekarz in a velour tracksuit and baseball cap. (The Reader is a fun place to work.)
Although I’m extra thankful to be typing in a Google doc right now, the process of creating the Reader didn’t magically get easier once computers came into the picture, especially as ad volume steadily increased. Videnovich, who did a bit of everything in her 17 years at the paper, also served as an archivist and web editor: “I manually converted and edited all the print files to HTML before there was an automated way to do it. I remember using dial-up to post the paper. It would take a while.”
Brett Murphy—classifieds advertising director from 1996 to 2008, advertising director from 2008-2010, and then digital sales director from 2010-2012 (for all Creative Loafing publications, including the Reader)—wrote to me about the transition into the Internet age for classified advertising.
He told me how Bob McCamant, a founding owner, along with others in IT, developed an in-house proprietary system for placing classifieds online with a credit card. People could browse ads in print and online for the first time, and especially for apartment rentals, this was a one-of-a-kind service in Chicago. Revenue exploded, and new customers flocked to the Reader. Around the same time, Reader Matches started booming as a dating service; Murphy noted that the “section was a very early model for what has become a vast stream of national online/mobile-based dating sites.”
In the mid- to late 1990s, Murphy saw the classifieds staff expand to manage the section, but “In the early 2000s, Craigslist expanded their free-listing business model for apartment listings into other markets including Chicago, and the popularity of Craigslist’s ‘free’ model slowly chipped away at the Reader classifieds business model until what was a slow drip of revenue decreasing became a gush of falling revenue for the entire company.”
There were efforts to explore new digital revenue streams in the following years, but Murphy wrote, “These streams paled in comparison to the ‘golden years’ of the classifieds department, when not only did we consider ourselves the best and most innovative classifieds listing database in the area, we believed we were the best in the entire country, producing multi-millions of dollars in revenue each year.”
The Reader classifieds section was truly something special for a while, and not just as a business practice. I can’t even count the number of people who have reminisced to me about the countdown to Thursday each week, knowing where and when the nearest Reader would drop, giddy to pick it up and devour it cover to cover—even back when it was the size of a college textbook.
David Jones remembers going just about anywhere in Chicago and seeing the Reader spread out on bar counters and restaurant tabletops, more often than not flipped open to section four, with eager highlights and pen markings from locals looking for a job, an apartment, or a date.
There was even a time when the classifieds section hit the black market, as copies snatched from a door ajar at the printer were sold on Wednesdays—one day early—for $1 each.
“Who knew?” Jones mused. “People were willing to pay a whole dollar for just a single section of the Chicago Reader, ‘Chicago’s Free Weekly.’”
And despite its fall from grace, Jones’s faith in the classifieds section as a Chicago institution, not just a Reader revenue-generator, hasn’t wavered: “The strength and the draw of our Classifieds section was undeniable all along, right up to the ‘Dawn of Craig.’ Yes, the money made there was always a big part of our meal ticket anyway, but there was also a sense of true community that formed around section four that transcended the commerce transacted there.”
Homes, careers, and other life-changing ads
When I decided to write this retrospective on classifieds, I wanted it to be more than just a history lesson; I wanted to directly include the voices of Chicagoans whose lives were altered by the Reader. So, I placed an ad in my own classifieds section about my classifieds article, seeking current or former classifieds clients who got a job, found an apartment, met a partner, or just generally changed course because of a classified ad (pretty meta, right?).
The positive responses were overwhelming, and it took me no time at all to learn that in Chicago, during a certain era of time, the Reader classifieds was the place to go, for almost anything you could imagine. (One of the greatest purposes the Reader served was in helping people find love—but I’m saving that for a different article.)
First of all, the pages of job ads were endless. Monica Brown, mentioned in the previous section, recalls that she probably got her job at the Reader through the Reader classifieds. Another source, Richard Knight Jr., was one of many people whose career paths were totally shaken up because they happened to be poring over the classifieds one day.
In late summer of 1985, Knight was three years deep into an office job in the Loop, playing Chicago clubs with his band on the side and seeking a change. He happened to spot an ad for an event planner (or party planner, he can’t remember) at Limelight, the “oh so chic mega nightclub that had just opened in River North and caused such a ruckus.” It felt like everyone in town was talking about Limelight, so he decided to call and ask about the job.
Knight remembers being abruptly and coldly denied—until he realized the voice on the other end was a mutual friend. Suddenly, the position wasn’t filled after all. The Limelight rep offered Knight an interview, noting that he was just turning away people who sounded too “straight.”
Knight notes, “The word ‘straight’ as Samuel used it didn’t mean heterosexual. It was a code word at the time for squares, bridge and tunnel types, 9-to-5ers, anyone who wasn’t cool and stayed up until 5 AM and kept vampire hours.” It turned out to be a good fit, and Knight got the job that pivoted his career completely.
To illustrate what a big deal house-hunting was in the Reader, I went back to the archives. The first issue in 1971 had no housing section at all, but two decades later, by 1991, there were 1,016 housing ads in the “one bedroom apartment” section alone. By 2001, there were 1,215 one-bedroom listings (I counted!). By 2011, just 122. Today, the Reader doesn’t have housing subsections, and the last issue had one, maybe two housing ads all together.
Trudy Ring, a journalist who lived in Chicago from 1984-1997, described that “picking up the Reader on Thursday afternoons was an absolute must! I did find my apartment through the Reader—the apartment in Edgewater that I stayed in the whole time I lived in Chicago! But I was a particular fan of the Personals . . .” (more on that later).
Betty Lark Ross found apartments in Old Town and Edgewater in the Reader, and she found a factory building for sale that she was able to convert into a home and studio. But she also used it to satisfy a treasure-hunting streak within the Reader classifieds buying and selling marketplace. She wrote to me, “During the home renovation, I discovered a classified ad that featured a brand new gigantic Kohler hot tub that could hold 6-8 people for $500. We opted to buy this and have it installed while it could be included in the design, and since money was tight, we chose to live without ceilings for a few years! We also only buy used cars, and to help with our move we bought a van advertised in the Reader for $500. We used it for two years and then sold it ‘as is’ for $500 when it needed brakes! While I truly miss the Reader classifieds, I am still a regular hunter-gatherer and seller on Craigslist, Nextdoor, and Facebook Marketplace.”
A final source, Elizabeth Mayer, wrote to me, “When I was getting ready to move here from Philadelphia in 1999, I found my apartment like this: A few days before a planned trip here, my in-Chicago sister got a paper copy of the Reader on the day it came out and priority-mailed it to me via USPS. I called several people whose listings sounded good (No pictures! So crazy!) and made appointments for when I was going to be in town a couple days later. It worked great—I found a place I really liked on Damen in Roscoe Village.”
A few weeks after that, Mayer helped move her sister into a Logan Square two-flat with a roommate she’d found in the Reader, who remains one of her closest friends.
“I realize neither of these stories is out of the ordinary—but that’s the point, right?” Mayer noted. “The classifieds were just how all that stuff got done.”
Free and freaky
I wouldn’t be painting an accurate representation of Reader classifieds if I didn’t talk about those Personals that Trudy Ring mentioned. Truly, before there was shitposting on Reddit, there was the Reader Personals section.
Pre-Internet, the alt-weekly was the best free public forum out there, where the chance for anonymity created an entire subculture of clever pseudonyms, cryptic exchanges, graphic messages, and a vast audience for those truly seeking to let their freak flags fly.
Ring told me, “I looked forward every Thursday to seeing the messages from Sparkler at 15, Basil Metabolism, Mental Floss, Boris and Doris Clitoris, Fritz Quadrata, Man of Many Pseuds, and more, even from resident conservative Rogers Parker,” she noted, revealing an impressive memory for the pseudonyms, some of which would appear in every issue. “They would comment on politics, movies, a little bit of everything, and some even offered little snippets of poetry—I remember Boris and Doris submitting some doggerel with rhymes including ‘adore us’ and ‘abhor us.’”
One of these characters, known to the Reader audience of 1975 as TigerLady, reached out to me to share her perspective. Today, she just goes by Kris Slawinski, but she fondly remembers poring over the Reader weekly in her early 20s. She started participating in the Personals dialogue in response to ads placed by Alex Hirka, aka ZaZa Lipsoidic. Around 1976, the Reader put out an interview with Hirka; Slawinski remembers, “[Hirka’s] ads were flavored with literary references and quotes, musical criticism, social commentary, and philosophy, which is what interested the Reader journalist who sought him out.” He was into punk rock and Patti Smith, which Slawinski notes was a “very rare thing back then.”
“ZaZa set a new standard for ads, sparking a flurry from an array of misfits who were looking for a virtual playground, before what we are familiar with today was even conceived. It was a very fun and interesting time,” Slawinski wrote to me in an e-mail. “I wound up meeting Alex/ZaZa through a series of provocative classified ads about music, and had a relationship with him beginning in very early 1977 (before La Mere Vipere, the first Chicago home for punk/new wave music, opened), until he moved to NYC in fall of 1977. We used to dance until closing at La Mere every night, where many of the new denizens of the Reader classifieds hung out.”
“I participated in the classifieds for several years,” Slawinski recalls, “with what I’m sure I’d now call pompous screeds.”
Other “screeds” that longtime Reader readers might recall include Critter Lady, Beautiful Dreamer, Jedi Knight, Manuel Dexterity—the list goes on. While many will go down in infamous obsolescence, others eventually came forward with their true identities. Some even met on a yearly basis to celebrate the camaraderie of the section, according to the Tribune.
They’re a part of Chicago history, like it or not—the anonymous, often snarky Personals contributors were conducting their own form of journalism back then, commenting on politics and pop culture and niche aspects of life in Chicago, albeit practically in code only some can decipher.
The classifieds section has changed so much over the years, and—unless Gen Z suddenly decides to adopt and prioritize print advertising and old-school dating methods—it’ll likely never be what it once was. But that’s OK!
I’m working with the rest of the Reader staff to create a classifieds section that caters to more than just ad agencies and a handful of less-than-tech-savvy local clients. We’re working on a brand-new website, a fully self-service option for anyone trying to reach our readers. All ads run both in print and online (unless requested otherwise), with focus on and discounts for categories like Mutual Aid, Community, and other local causes that help the people and culture of Chicago.
Classifieds may not have the mass that it used to, but as long as the Reader is around—and we’re hoping for at least another 50 years—it will remain an invaluable archive and incredible time capsule of the pre- and post-Internet-creation days of Chicago. Whether it’s job hunting, house hunting, buying and selling, or whatever else you can imagine, the classifieds section of the Chicago Reader is iconic in the way that it allows community members to interact with their local and independent alternative newspaper, and frankly, that’s a legacy I’m proud to be a part of.