1. The Simpsons head-box DVD sets

Starting with the sixth season of The Simpsons, Matt Groening and company offered up DVD sets encased in limited-edition "Simpsons Head" boxes, slick plastic shells modeled after the show's stars. (Season six was Homer, Season seven was Marge, and so forth.) But as is so often the case with poorly designed packaging, whimsical form far outstripped functionality. For one, the heads are extremely difficult to open, equivalent to cracking the seal on a jelly jar with grease-slicked fingers. Once opened, they sprayed out a bunch of loose, unsecured material (special-offer cards, an X-ray of Homer's brain with a pencil jammed inside it, etc.). And over time, the flimsy paper jacket covering the discs and keeping the liner notes in place inevitably fell apart. The outrage over the Simpsons Heads was so strong that Groening set up a website where disgruntled buyers could exchange their heads for the boring old box packaging of the previous seasons. But first, he castigated fans for failing to embrace his whimsical conceit.


2. The Herbie Hancock Box tower


Columbia's vault-clearing Miles Davis CD sets established a high standard for jazz reissues. A CD set dedicated to Herbie Hancock's tenure on the label—during which he helped pioneer fusion, funk, and electronic music while still keeping one foot in his post-bop '60s past—was no exception. And the packaging only added to the appeal. Its four discs arrived in a clear plastic cube that made them appear to float in mid-air. But problems began when purchasers actually tried to listen to the discs—they tended to fall out as soon as the box was opened, and it required Michael Jordan-esque levels of coordination to return them to their original positions. As an objet d'art, The Herbie Hancock Box lived up to the material inside, but it made that material even more inaccessible than its subject's wildest excursions.

3. Fargo snow globes

Even the best VHS tapes made for unsatisfying viewing. Even if they looked and sounded great (which they almost never did), their clunky size and the way even minimal repeated use wore them out made them pretty damn uncollectible. Nonetheless, studios kept trying to start a collectors' market, often adding incentives for those who needed to watch, say, Cliffhanger at a moment's notice, but remained too cheap to shell out for a laserdisc player. In 1997, Polygram cleverly marketed Fargo by selling the VHS packaged with a snow globe depicting a tiny Frances McDormand kneeling over a corpse in the snow. A second globe, featuring the infamous wood-chipper scene, followed a bit later. Great idea, but unfortunately, Polygram didn't bother to create particularly good snow globes. The water turned yellow with exposure to light, leaving poor McDormand drowning in what appeared to be a sea of urine, a grimmer image than even the Coens imagined. Worse yet, the things tended to leak over time, leading to "urine"-soaked tapes on store shelves.


4. Public Image Limited's Metal Box canister


PiL's second album continued John Lydon's attempts to move beyond the punk of the Sex Pistols and toward something more abstract, and sometimes aggressively unmusical. In keeping with that spirit, Metal Box was originally released on three 12-inch 45s, and packaged in a film canister. The hi-fi vinyl format suited the songs—"This is tactile music," Trouser Press raved—but the canister itself proved problematic. Aside from being difficult to file, Metal Box's metal box dinged easily, making it tough to fit the records back inside. Plus, the records themselves sometimes warped after spending time in the can. After an initial run of 60,000 copies, Metal Box was reissued as a standard double album, and re-titled Second Edition. The sound suffered, but not the storage.

5. Sex And The City's thin-plastic DVD sets

Say this for the Sex And The City DVDs: At least their makers had the courage to see a horribly botched conception all the way through. The show's six seasons (including half-seasons at non-budget prices) were all packaged in a transparent tinted plastic that, on the surface, cleverly mimics the suggestiveness of high-end lingerie. But the plastic is as brittle as Sarah Jessica Parker's heart: After a few uses, the spine tends to break off on all the individual discs, leaving collectors to arrange the seasons in a series of color-coded piles.


6. Spectrum's Soul Kiss (Glide Divide) oil-blister sleeve


Pete "Sonic Boom" Kember's first post-Spacemen 3 full-length was a doozy, both sonically and in its limited-edition packaging: Soul Kiss (Glide Divine) came in a supposedly watertight PVC sleeve filled with a goopy mixture of colored oil and water. It looked pretty great, except when it burst in transit and ruined the records around it. Or when, years later, it dried up into a hard, crackly rock. On top of that, getting the LP (and presumably the CD) out of the sleeve was tricky. No album should require its own waterproof storage area.

7. Spiritualized's Ladies And Gentlemen We Are Floating In Space drug-themed containers


Sonic Boom's Spacemen 3 partner, Jason "Spaceman" Pierce, has had plenty of goofy packaging ideas, too, but none more completely insane than for his masterwork, Ladies And Gentlemen We Are Floating In Space. He had to top the glow-in-the-dark plastic box of Pure Phase, so Pierce offered Ladies in various drug-related configurations. The front cover was designed to look like a box of medicine, and Pierce took the idea even further: You could get the single disc version in a special cardboard-and-foil package, so the CD popped out like a pill. (And once you cut the aluminum, it would never be in mint condition again.) That's fine. But for the super-limited version, Pierce took things even further: The album was available on 12 individual 3-inch CDs, all held together in a foil blister pack that looked like a box of pills. Awesome idea, but horrible if you just want to listen to the record.


8. The Total Recall: Special Limited Edition DVD Mars box


Paul Verhoeven's 1990 Philip K. Dick adaptation is set on Mars. Mars is round. DVDs are round… So why not package the disc in a Mars-shaped tin? Here's why: Round objects don't shelve well. Artisan's solution of resting the tin in a flimsy cardboard cradle didn't solve the problem. Once the cardboard piece bent, tore, got lost, or got sat on, Arnold Schwarzenegger's quest to bring a blue sky to Mars was free to roll under the couch.

9. Sting's Soul Cages puzzlebox packaging

Back when Sting released his third solo album in 1991, CDs were an affront to the environment: They were not only housed in landfill-clogging, non-biodegradable jewel cases, they were also displayed in "longboxes" composed of cardboard sleeves three times the size of the actual product. So tip of the hat to Sting-a-ling-ding-ding for trying to break the mold on The Soul Cages by fusing the two together in a more green-conscious way: Compressing the cardboard longbox into a multi-fold, biodegradable digipack for easy shelving. Unfortunately, this opened the door for another bad packaging habit by forcing listeners to unfold gate after gate after gate to finally reach the CD. And in this case, all that work yields little reward.


10. The Durutti Column's Return Of The Durutti Column sandpaper sleeve


One of the many ways Manchester's Factory Records strove to set itself apart from the rest of the UK punk pack was with its record covers, which were often more like modernist art than commercial design. The 1980 release The Return Of The Durutti Column was packaged in a jacket made of sandpaper, borrowing an idea from Guy Debord's Situationist art-and-essay collection Mémoires. Anything the cover touched—particularly the albums next to Return on the shelf—got scuffed, marred, or outright destroyed. It was a clever, aggressively punk concept in theory, but obnoxious in practice.

11. The Memento limited-edition DVD features barrier

Most complaints about the limited-edition double-disc Memento DVD have to do with its not-as-cool-as-it-sounds special-features menu, which requires users to correctly respond to a series of vague psychological tests in order to access goodies like a poster gallery and a chronological edit of the film. (The tests are fun at first, but impractical and annoying in the long run.) But just as bothersome is the actual DVD package: a fake case file on the movie's protagonist, "Leonard Shelby." The box looks neat, but the papers in the file are packed so tightly that it's difficult to remove the DVDs. Tugging at the box causes the dossier to permanently loosen, letting the papers inside flop free. Over time, the package degrades further—just like Leonard.


12. The cassingle


As a music-delivery device, 7-inch 45-rpm singles were sublime. They were cheap and portable, and people who bought them knew they were getting easy access to a song they already liked. But when vinyl started to lag in popularity behind cassette tapes, the industry had to find some way to keep the singles market active, so they introduced the cassingle, which put all the molded plastic and tiny gears of a cassette tape to work on delivering two or three songs—or in some cases, only one, repeated on both sides. Cassingles were easy to lose, easy to break, and—given that most were packaged in flimsy cardboard sleeves—tough to store. The standard cassingle "storage case" was the floorboard of a car, between an empty plastic bottle and some stale french fries.

13. Whatever: The '90s Pop & Culture Box's coffee-top


To capture the essence of the '90s, Rhino packaged a decade-summarizing CD set in a box with a plastic cover sleeve containing actual coffee beans. The coffee smell is strong—and persistent, lingering for years after the purchase—but the bigger problem with the box is that if the plastic cover gets breached, then beans and coffee dust spill all over the floor every time the set is touched or moved. (Though come to think of it, the '90s were a time of powerful odors and inconvenient messes.)

14. UNKLE's War Stories "treasure chest"

The limited-edition version of UNKLE's War Stories required the band to post instructions on how to open it. We'll let those instructions explain the calamity: 1) Pull the sides apart for about a minute to loosen up the outside package and let air in. 2) Grab the box with the sliding end facing away from you and shake it hard for a couple of minutes. 3) Once the inner case slides out a bit, grab it and pull. 4) Smile because you've opened the new UNKLE treasure chest. 5) Put the CD in, turn up the volume, check out the artwork in the booklet and enjoy! (Alternate suggested step five: Don't kill us for making you ruin your expensive disc!)


15. Mad Men's season-one DVD lighter box


Although it's now available in a standard cardboard box, the original release of the hit AMC series Mad Men came in a metallic replica of a Zippo lighter bearing the show's logo. This was embarrassing enough on its own—it resembled a big novelty lighter from Spencer's Gifts, or the nearest roadside Stuckey's—but it also necessitated stacking the discs in a tiered foam holder that made it easy to scratch the playing surfaces. Worst of all, it took the show's lovingly crafted, precise evocation of the hard-drinking, chain-smoking world of early-'60s ad execs and swapped it out for cheesy novelty appeal. Plus, it wouldn't even light your Lucky!

16. The Strangers With Candy: The Complete Series Trapper Keeper


When Amy Sedaris' cult hit Strangers With Candy was released in a series-spanning collection, the designers hit on the idea of making it look like a Trapper-Keeper, the ubiquitous high-school notebook binder of the 1980s. It was a neat idea, perfectly suiting the afterschool-special-gone-horribly-wrong vibe of the surreal sitcom, and it allowed them to throw a bunch of jokes, photos, drawings, and quotes onto the interior of the package. Unfortunately, for practical use, it was a mess: The fuzzy Velcro tab used to close the package either didn't work or fell off, the discs were held loosely onto flimsy cardboard instead of sturdy plastic, and the whole package was angled like a binder, which meant that it didn't look right on a shelf, and couldn't be stacked. It soon became the laughingstock of Flatpoint High.

17. Goddamn motherfucking security tape

The little strips of tape that seal the tops, corners, and edges of new CDs and DVDs have become, alongside airline food and car alarms, a favorite target of hacky standup comics. But just because a lot of rotten comedians hate security tape doesn't make it any less sucky. Security tape has replaced the dreadful Blister-Pak as the single most infuriating development in the history of consumer packaging; it's incredibly difficult to remove, yet totally flimsy, so cheap that it comes apart in your fingers when you try to pull it off the product, but so tenacious that it often leaves the case permanently marred with glue residue that picks up dust and lint. And in the case of DVDs where the inner paper sleeve isn't completely centered within the protective plastic, the security tape frequently attaches to the paper and rips it apart in chunks. You know you're dealing with truly epic bad packaging when it actually destroys the thing it's meant to protect. The crowning insult is that security tape isn't even necessary: it's placed beneath an external layer of shrink-wrap that already prevents theft, and is often combined with a magnetic "screamer" on a product that usually costs no more than $20 in the first place. There's a special place in designer's hell for whoever invented security tape; there, he will forever shred his fingernails clawing through endless layers of his own creation.


18. Kenny G CDs

The vast majority of CDs released by soft-jazz saxman Kenny Gorelick suffer from packaging that is, if anything, designed too well. The jewel cases hold the discs firmly in place, preventing them from coming loose inside the case, where they can become scratched and unplayable. If that isn't bad product design, we don't know what is.