For our amusement (and yours, too, we hope) we dug up 40 covers that made us laugh, puzzled us, or—in many cases—freaked us out. Click the thumbnails below to launch the gallery. For more covers, check out our archives.
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1 / 40
1970: Our first cover was a nightmarish composition that foresaw Cirque de Soleil, Blue Man Group, and Devo. -
2 / 40
1971: Because nothing sells magazines like a culturally insensitive pastiche involving a smug Godzilla slurping indistinct Asian food. -
3 / 40
1972: The lesson here is obvious: Whatever burning question is keeping you awake at night right now will, in 38 years, make no @#$%ing sense. -
4 / 40
1973: Tennis: Everybody’s doing it! Except the fanatical kid near the middle of the cover, who would rather behead his sister than play tennis. -
5 / 40
1974: “OK, Sergeant Bailey, now let’s try some shots with the pants off . . . No, no, keep the gag on. The handcuffs? I’ll loosen them in a minute.” -
6 / 40
1975: That was the year every one of our covers looked like an Emerson, Lake, and Palmer album. -
7 / 40
1976: What’s in that apple? PCP? These two look like they’ve been running naked through Lincoln Park for two days. -
8 / 40
1977: This one is so bizarre I don’t know where to start. Is it the cooing Vincent Price on the left? The constipated Vincent Price on the right? Or the fact that we put two frickin’ Vincent Prices on the cover of a restaurant issue? -
9 / 40
1978: Let’s see, we’ve got doves, campaign buttons, a guy on a horse, and a dude in a gas mask. Was this a riot or a freak show? -
10 / 40
1979: “Well, no wonder you couldn’t sleep last night, honey. You’ve still got that El train, Picasso sculpture, and tiny boxer in your pillowcase!” -
11 / 40
1980: You should see its genitalia. -
12 / 40
1981: Who serves the best steaks in town? The Kelsons know! And mini Carlton Fisk obviously has no idea. -
13 / 40
1982: The presence of the model’s Witness Protection Program liaison complicated the photo session considerably. -
14 / 40
1983: Ah, who doesn’t long for the halcyon days when Chicago’s Top Restaurants served culinary classics like pearls on dehydrated bananas? -
15 / 40
1984: Ah, the notorious pop-up cover that terrorized newsstands, broke subscribers’ noses, and launched the seven-figure class-action lawsuit. Our lawyers warned us, but did we listen? No. -
16 / 40
1985: Federal Judge Prentice H. Marshall proves once and for all that justice isn’t blind. But it’s nearsighted and has cataracts and astigmatism. -
17 / 40
1986: Can the defense do it again? this provocative cover asks. If “it” means “Get their asses handed to them by the Redskins two months later in the playoffs,” then the answer is an emphatic yes. -
18 / 40
1987: Few remember now, but it was once the height of fashion for swimsuits to come equipped with their own retractable butt-flags. -
19 / 40
1988: The Genius of Jim McMahon? The custom-made sunglasses that sprayed whiskey directly into his corneas. -
20 / 40
1989: The irony is she looks cold and dry. Guess that’s the danger of shooting a June cover in April in Chicago. -
21 / 40
1990: Long after her Boogie Nights ended, the ever-plucky Rollergirl still clung to her modeling dreams. -
22 / 40
1991: If I had a dime for every night that ended with a bushy-haired chick in a red dress serenading me with a saxophone on a rooftop downtown, I’d buy us all a round. -
23 / 40
1992: The original headline, “Shrimp! Four of ’Em!” was overruled at the last minute by the editor-in-chief. -
24 / 40
1993: The original headline, “How to Convince Old People to Cancel Their Subscriptions,” was overruled at the last minute by the editor-in-chief. -
25 / 40
1994: I’ve always loved this one, not only for the impeccable composition, but also for the fact that she looks like a girl who rejected me in college, and I’m thrilled that she ended up a bartender. -
26 / 40
1995: Ah, yes. Crippling budget issues at the end of 1995 forced us to do this cover with scissors and a magic marker. -
27 / 40
1996: Whoever put the reflection of the Chicago skyline in her earrings was a genius. Or did she buy Chicago skyline earrings from one of those kiosks at Navy Pier? -
28 / 40
1997: You can tell these two hate the water, hate each other, and hate the whole concept they’re being subjected to. That’s newsstand gold! -
29 / 40
1998: Shortly after this picture was taken, a cockatoo flew out of her hair and attacked the photographer. -
30 / 40
1999: The guy on the bottom right, we found out later, had actually been dead for a month. Cutest rigor mortis ever! -
31 / 40
2000: Another couple that obviously can’t stand each other. (She: “Your breath smells like regurgitated tapioca.” He: “I peed in your popcorn.”) -
32 / 40
2001: Surviving O’Hare? Not as easy as you think when you’re in danger of having planes fly into your fur hat. -
33 / 40
2002: And when the judge found him in contempt of court, he tore off his pants and showed his “habeas tuchus” tattoo. -
34 / 40
2003: Thumbs! They’re overrated. No, wait, they’re underrated. -
35 / 40
2004: Maybe it’s just me, but Nicole Kidman’s last facelift finally took things too far. -
36 / 40
2005: This is a still shot from the pilot of TV’s little-known precursor to Mad Men: Vaguely Dissatisfied Men. -
37 / 40
2006: Great Getaways, huh? The first getaway must have been the flesh from this malnourished rack of bones. -
38 / 40
2007: Her look cracks me up. It says, “I’m mysterious and aloof, yet enlightened,” when it should be, “Holy shit, I’ve got a @#$%ing monkey on my shoulder!” -
39 / 40
2008: I believe I fought for the exclamation point on this one. You know, because 64 ounces of a charred bloody cow didn’t make the issue’s editorial focus clear enough. -
40 / 40
2009: Apparently the exclamation point thing worked out well the previous year.