Some of our memorable covers and stories in the last 40 years. For more covers from the past four decades, click here »

Perhaps you’ve heard this publication is turning 40, an occasion that affords us a certain amount of navel-gazing because so few magazines survive this long. Some titles sound good but fizzle fast (Talk, Cookie); some burn bright and flame out (Spy, Jane); others probably never should have launched to begin with (I’m looking at you, Mary-Kate and Ashley). In honor of our ruby anniversary, I venture farther into the umbilicus to celebrate my favorite moments in Chicago’s history. I would have listed 40, but I only got one page.

Editor’s note: We tried our best to locate the stories referenced in this column, but some articles were published before we started keeping electronic files. For those, we have linked to pdf files.

Best Launching Pad
Studs Terkel, a contributor, publishes excerpts (pdf) from his new book, Working, which becomes a bestseller and inspires a Broadway musical, a Second City revue, a graphic novel by Harvey Pekar, and a song by James Taylor. (March 1974).

Story That Still Gives Me Nightmares
Dangerous Therapy, by Cynthia Hanson, about a woman who became convinced during hypnosis that she possessed 300 personalities, had feasted on human flesh, and had sexually abused her sons. (June 1998)

Most Enticing Headline
The Strange Case of the Dentist and the Pimp, Bryan Smith’s bizarre crime story about a dentist. And a pimp. (October 2006)

Triggered the Most Canceled Subscriptions
That time we put a naked lady on the cover (above, left), seated at a typewriter and wearing only a hat and high heels. (December 1993)

Angered the Most Foodies
That time we took away half of Charlie Trotter’s fourth star, prompting a storm of letters and e-mails that only stopped seven months later when he got it back. (March 1999)

Angered the Most Celebrities
Those times we published photos of homes of the stars, drawing the ire of Michael Jordan, Billy Corgan, and Ed Burke, among others. (October 1994 and 1995)

Most Significant Quote, in Retrospect
“I’ll run [for office] if I feel I can accomplish more that way than agitating from the outside.” —Barack Obama, the “tall, affable workaholic” we profiled (above, second from left) for his voter-registration efforts among African Americans (January 1993) Read the story and check out our collection of stories about Obama.

Most Prescient Award
Louise Erdrich—a broke 28-year-old—submits a piece of short fiction, “The World’s Greatest Fisherman,” (pdf) which wins our inaugural Nelson Algren Award and launches her career as a novelist. (October 1982)

Loopiest Cover
A surreal pastiche (above, right) for Before They Were Famous that includes Donald Rumsfeld dressed as a Boy Scout and David Hasselhoff as Hamlet. (February 2007)

Eviscerating Irv Kupcinet in 42 Words
“He is the verbal equivalent of a fucky-knuckles; a person, that is, who is always dropping things. Kup drops language. . . . Saul Bellow swears that on his one appearance on Kup’s Show, Kup cited his novella Seize the Day as Seize the Dog.” —Joe Epstein, in a profile (pdf) of the legendary Sun-Times columnist (July 1977)

Photo That Influenced a Presidential Election and Still Pisses People Off
Jeff Sciortino’s incendiary shot (above, second from right) of the former Communist revolutionary Bill Ayers standing on a U.S. flag, which resurfaced during Obama’s 2008 campaign. (August 2001)

Biggest Gross-out
Riding with the Rat Patrol (pdf), Edwin Black’s gonzo tale about three city workers attempting to eradicate a swarm of rats overrunning the Chicago Park District. (August 1971)

Best Lead
“Early August, 1969. During my first hour in Cook County I was offered a bribe. By my prospective father-in-law. To not marry his daughter. Goddamn, I’m gonna miss this place.” —from Friendly Confines (pdf), by Lenny Kleinfeld (January 1987)