The Lisa (1983)
In all fairness, most of those early personal computers from the 1980s are pretty hideous. But there’s something particularly unattractive about this model (which was also a commercial failure), from those prominently displayed twin floppy drives to the boxy, one-button mouse. Plus, y’know, beige. Luckily, the company would eventually realize the importance of color in design…
JLPGA PowerBook 170 (1992)
Aaaacckkk! Bring back the beige! In all fairness, Apple only manufactured 500 of this PowerBook 170 variation, specifically for the 1992 JLPGA golf tournament in Japan. But if you’re making a special collectors’ computer, why would you want to make it look like a beginner’s Crayola box threw up?
The eMate 300 (1997)
Apple’s first attempt at a low-cost, student-geared laptop only lasted a year — partly because it used the less-than-beloved Newton operating system, but surely done no favors by the unfortunate clamshell design. The dark green version was most popular, but get a load of that orange monster. Yikes.
The iBook G3 (1999)
The orange monster strikes again! The original iBook looked like the bastard child of the eBook and an original iMac, with a dash of toilet seat thrown in. The orange was, again, the most unfortunate of the color choices; the designers also tried to sell us on a plastic handle, allowing students to carry it like a little briefcase, a look which literally nobody could pull off. Evidence:
Power Macintosh G3 All-In-One (1998)
Inexplicably developed at the same time as the sleeker and far more commercial iMac, this attempt to create an all-in-one unit died a quick death — though it’s worth investigating its influence on the look of Pixar’s WALL-E.
The “Flower Power” iMac (2001)
Look, I know there are only so many colors you can slap on an iMac to keep it fresh. But I think I speak for everyone when I say this model is more blech than far out, man.
Twentieth Anniversary Mac (1997)
As advertised, this “luxury” Mac was developed in celebration of Apple’s 20th year, yet somehow they ended up with what looks like a keyboard attached to one of those wall-mounted CD players. Or maybe one end of a home security system. But that’s okay — it was priced at a super-reasonable $7,499. Hey, the keyboard palm rests were made of leather! That stuff costs money!
The Newton MessagePad (1993)
Now fondly recalled as the “original iPad,” Apple’s first personal digital assistant device was, let’s face it, a big ugly black box that looks more like a supermarket credit-card interface than the future of tablet computing.
iPod Shuffle (first generation) (2005)
Though the iPod mini-player would ultimately shrink down to roughly the size of a silver dollar (thus ensuring an endless cycle of losing/re-buying among absent-minded consumers), the first iteration was a strange, memory-stick-reminiscent device that looked less like an mp3 player than a home pregnancy test. It’s a boy… band!
The iPod U2 Special Edition (2004)
At risk of looking even less cool than I already am, here’s my confession: I love U2. And even I didn’t spend the $349 for this 20 GB “special edition” iPod ($50 more than that year’s regular model), which adopted the band’s How to Dismantle an Atomic Bomb color scheme and came with their autographs engraved on the back. (It also included a coupon giving buyers $50 off the $150 “Complete U2 Digital Box Set,” since anyone who was enough of a U2 fan to buy their personal iPod would obviously not already have all their mp3s, but I digress.)