The North Side golden hour encompasses a small condo with a view of the city below at the corner of Addison Street and Lake Shore Drive. A woman sits at her kitchen table and pops open a Diet Coke. Barbara Hoffman, known as Barbie to some friends and family, is waking up for the day with the sunset.

A decorative bowl full of sunglasses sits on an end table nearby, maybe to ward off some of the damage from all the strong sunsets she sees through the windows and keep the degeneration in her right eye at bay.

“I always had beautiful views,” she said.

This isn’t considered one of those beautiful views for Hoffman, who’s more accustomed to a high-rise in downtown Chicago than a golden-blue view of the North Side, spotted with the other condominiums, shorter diners and friendly Mexican restaurants of Boystown. Youth clustered the streets on a Friday night as Hoffman reflected on her own youthful experiences in the city, arguably much different than that of the small figures of adolescence below.

However, the idea remains the same. For Hoffman, sometimes play was work and work was play.

This was certainly the attitude at Playboy magazine, where Hoffman worked on the 10th floor offices on Michigan Avenue as an assistant secretary for Arthur Paul, an art director at Playboy known simply as Art by friends, family and coworkers. Paul was the man to design the famous Playboy bunny logo, and to first have the idea of bringing illustrations into the magazine instead of just photographs, which, according to Hoffman, not a lot of other magazines were doing at the time. Back then, Playboy was a revolutionary socialite magazine, enthralling its readers in the clubs and party scene of ‘70s Chicago, sometimes drawing sharp controversy for its portrayal of women.

Hoffman now spends her days working on crossword lottery tickets or going out with friends from Playboy, according to granddaughter Alexandria Dravillas.

“Playboy was her life and it still is,” Dravillas said. “Whether it’s dinner, a show or playing cards, she’s booked five out of seven days of the week.”

Hoffman’s platinum blonde hair rests in beehive style on top of her head. The all-black outfit she wears contrasts with the blue eyeliner under her lids, and her large, silver jewelry glints in the sunset. Her shoes shine. Around the living room sits a collection of art books, framed art, small sculptures and plants – and that’s about it. Save an L-shaped couch, coffee table, television and small kitchen table, furniture numbers few. She doesn’t have room for much else, as the crowded yellow ‘70s kitchen is filled up with plants and art.

“I did all sorts of crazy things for Art,” Hoffman said. “But at the same time he taught me about the art and what they do and how they do it. It’s the job that was so interesting.”

When Hoffman started working for Paul, tasks were strictly secretarial – making coffee, planning the meetings, preparing anything else he might need as an art director. She didn’t care so much about the art as she did having a decent job. That view quickly changed.

Hoffman, who worked at Playboy for the 32 years between 1973 and 2005, saw shipment after shipment of famous, contemporary artwork in and out of the offices, from Dali to Picasso. She developed a bond not only with her coworkers, but with the art collected by the magazine. It became her job not just to know all about the art, but to look after it. No one else had the caretaker personality of Hoffman – every single art director in her time there was male.

So Hoffman took charge.

When Paul left Playboy and Hoffman became secretary for art director Tom Staebler, her secretarial position didn’t last long. She soon became art curator, changing up the exhibitions in New York City and L.A.  —  traveling for work, redesigning all the major offices, cleaning the artwork and even sometimes looking after all the art directors when they went out for a celebration and got rowdy. After one particularly turbulent night, Maxine’s, a restaurant on the Near North Side, asked the bunch not to return.

While all the art directors were artists themselves, it was Hoffman who stepped outside of her mandatory duties and began archiving all the art Playboy collected, studying it as she went. In 2010, about five years after Hoffman left, Playboy sold part of its collection – 80 photographs, more than a dozen contemporary works and 24 cartoons brought in nearly $3 million. They had an archive of 5,000 contemporary artworks and more than 20 million photographs as of 2010.

“Strangely enough it was all there in front of me, and nobody was seeing it because nobody was doing it,” Hoffman said. “That’s when the computers came in.”

Hoffman took on the job of organizing all the art archives on computers in the late ‘80s, when digital archives were on the horizon. Hoffman has a knack for trendsetting and forbearance, having worked alone on the entire project except for one younger assistant, Frank Folino.

She also started a group called the Association of Art Curators, which acted as a support group for art curators and directors across the country. They would provide feedback to each other, and have the opportunity to discuss what was and wasn’t working in their exhibition designs.

Hoffman’s desire to preserve and collect art didn’t just stay in the office though.

Her condominium walls burst with artwork she’s been collecting since 1973. Hidden on the wall between the kitchen and the living room hangs a provocative line drawing of a man and woman by Art Paul himself, given to her by former CEO Christie Hefner, daughter of Playboy founder Hugh Hefner. Christie was one of the first to advocate for Hoffman’s promotion to art curator, and they still get together from time to time.

Hoffman flips through an old scrapbook, the insides a shiny mauve. She saves all the old notes and illustrations from her coworkers at Playboy in one large book, the insides just as bursting with art as the walls around her. Coffee-stained letters followed cutesy illustrations of Hoffman at work from the art directors.

One illustration, which acted as a note from Paul, shows Hoffman asleep on a pillow at her desk. “Mrs. Hoffman is on her lunch break and will return in a short time.”

Hoffman knows that all work and no play makes everyone dull. The whole office seemed to live by this saying, she said.

“I [get] in about 9:15 [a.m.] every day,” Hoffman said. “I should be there [at] 9 [a.m.] but I live across the street and I get there at 9:15, and I’m not a morning person, so about 10:30 [a.m.] I put a little note on my door and say early lunch, back in a half hour. I had a little blanket and a little pillow and I’d take a little nap.”

Hoffman still lives by the same saying. She complains about her small condo far away from downtown, but doesn’t have the money to move where she’d like to live, she said. She spent too much of it when she was young and didn’t think enough about her retirement fund, which is now too small for her to move elsewhere.

But the fun was worth it.

“The parties that we would have were parties you read about,” Hoffman said. “They were wild. Everybody had fun.”

There’s a picture in her scrapbook of what everyone supposed was Hoffman’s 40th birthday party at the apartment of Chester Suski, another art director. It was really her 45th birthday.

“Are you kissing him? With your eyes open?” asked Dravillas as she looks at the scrapbook memories.

“Yeah, that’s me!”

At the party, Suski had everybody wear a print-out mask of Hoffman’s face. There were semi-nude dancers, a 6-foot cake with sparklers and a man in a bikini to jump out of it, according to Suski.

“When she walked in the room she saw herself everywhere, 50 or 60 people, everyone had this image of her face on their body,” Suski said. “Back then everybody dressed up…it was another world.”

Suski, Hoffman, Paul and the others still keep in touch to this day. They see each other more than some family members.

“It seemed as if not another magazine would last as long, except for maybe the Bible,” Suski said.

Hoffman saves a lot of memories in her giant book, and even more in her head. “Partygoers Peek at Playboy’s New Sky-High Hutch,” reads a Chicago Sun-Times headline that she has clipped out for the scrapbook. According to Hoffman, Playboy won more art awards than any other magazine during its heyday.

While Hoffman still makes time for Playboy friends today, she has some favorite locales in her Boystown neighborhood, too. There’s a Mexican restaurant on Broadway Avenue, about five blocks away from her condo. She and Dravillas take an Uber to get there, taking it easy on Hoffman’s bad knee. At El Mariachi Tequila Restaurant, the server hugs her hello – “It’s been a while!”

After dinner with a blue margarita, it’s coffee for dessert.

“Caffeine does nothing to me,” Hoffman said.

Header illustration by Victoria Williamson