The news that Steve Jobs is leaving Apple has rocked the tech world over the past week. Beyond that, Apple’s momentous rise over the past two years has made it one of the most valuable companies (and stocks to own) in the US.

But that success hasn’t been going on forever. Sure Apple gave us the iPod, iPhone, and iPad, but here are five products that just plain failed. Rotten apples, you could say:

5. Pippin (1996)

Ah the Pippin, with its AppleJack controller, 14.4 modem, and $600 price point.

Nintendo 64 it was not.

This gaming console PC cost way too much back in the day, and it’s modem made things impossibility slow, even by 1996 WWW standards.

Considering that N64 was about $200 back then, the Pippin never stood a chance.

4. Twentieth Anniversary Macintosh (1997)

There were some innovations here. The TAM was one of the first desktops to use an LCD screen. It also had a Bose speaker system that sounded amazing, and its design was futuristic and playful. For that reason, it was not a total failure.

But its $7,000 price was unheard of, even by Apple standards, even in the 90s.

When you throw in the fact that the TAM was just a Power Mac 6500 with speakers and a monitor for more than $4,000 extra … yeah …

3. QuickTake (1994)

If the QuickTake came out in the late 80s or even 1990, it would be marveled, up there with the Apple II, as something revolutionary, that helped usher in a new generation of tech toys.

But it came out in the mid 90s, when a dozen other companies were racing to put out much better products.

The QuickTake was one of the first digital cameras.

But it only took pictures in 640×480 resolution, had no focus, and only stored eight photos.

The camera was also designed to work with a Mac, instantly limiting its market share.

2. MobileMe

The technology is there. The clouds are there. There is and was nothing revolutionary or impossible or really even that difficult about what MobileMe was designed to do: allow users to access and edit their photos, files, contacts, and calendars from a remote location.

The problem was simple: It didn’t work correctly when it launched. The buggy launch of MobileMe helped usher its demise, along with a 50-cal slug from iCloud.

1. The Apple Lisa (1983)

Reportedly named after Jobs’ daughter, who was born when development started, the Local Integrated Software Architecture computer was Apple’s first try at a GUI-driven computer.

The computer was marketed at businesses, but it’s $10,000 price tag drove away even the hungriest greasy-handed IT department computer nerds.

Some would say the Lisa was a success because it helped usher in the Macintosh in 1984, but that wasn’t the case at all. Businesses and home users flocked to IBM’s cheaper personal computers in the early 80s, cementing the PC as the dominant platform. Apple would never recover.

For that reason, we name the Lisa the biggest failure, in our minds, in Apple’s history. The company rules the tablet PC market and a good chunk of the mobile phone market. It has a monopoly on the portable music market. But it has never, and will never, dominate the desktop computer market, and part of the reason is because IT departments almost always buy the same “type” when they upgrade, partly because of software costs. Therefore, WINDOWS is still what’s in nearly every office and most homes.

Purposefully not on the list

The ROKR.

OK, so nobody likes the ROKR. They still bought it — a lot of them did.

At least 16 different Motorola ROKR cell phone models have been built since 2005, with the latest coming out in June 2009. It is a phone designed to carry your iTunes music. If that’s all you want, and some phone calls, then the phone worked fine. No reason to add any additional hate. No matter how lame the piece of crap is.

NeXT

Not an Apple product, but it was a Steve Jobs product. Apple bought it eventually. The computer didn’t sell well, and the platform it was built on was short lived, but this product is not a failure for one simple reason: In 1991 it was used to create the first web server.

Newton

Can’t call the Newton a failure. It was the first PDA ever. Apple CEO John Sculley actually coined the phrase “Personal Digital Assistant.” So what if it cost too much and the Palm Pilot would soon demolish it?

With a name like, ‘The Penal Zone,’ you know you’re in for something ridiculous. Sam and Max: The Devil’s Playhouse: Ep.1 – The Penal Zone from Telltale Games is a pretty casual experience that is heavy on dick jokes and, sadly, somewhat short on overall entertainment.

Sam and Max are a 50-style cartoon detective crew (animals — mind you: a chubby, insecure dog and a twisted bunny) that seem to have gained most of their popularity through the consistent release of games they are featured in (3 seasons worth now), rather than through traditional comic book success. Previous games in this series have reviewed reasonably well, though this game was my first experience with the franchise.

The Penal Zone is the first in a 5-episode series of point and click adventures that relies heavily on nerdy bathroom humor to try to coerce you through a series of elaborate brain teasers. You walk around as Sam, the dog in a suit, and collect items of various consequence, after a suspicious space-gorilla has landed in the middle of your block. It’s up to your crack detective work to determine what to do with the items and when to use them. Some can be given to other characters in order to advance the story, some will be useful only through further analysis and others will be placed in the environment at appropriate spots to trigger puzzle solutions or advance plot points.

Sam’s sidekick Max serves as a wild card character that has been bestowed with a set of powerful psychic abilities. He is able to use the ‘Toys of Destruction’ that give him the power to see the future and teleport between phones, in addition to some other briefly used but notable abilities. One very interesting trick is the ability to teleport to a phone that you have on you. You can leave it in places or get separated and teleport back to it for clever solutions to several problems and puzzles in the game.

There are some fun elements to The Penal Zone — just saying it for one – and a number of wacky tools the game offers you to be used in a number of creative ways. The lead villain, General Skun’ka’pe, meaning skunk-ape, is for sure the best character in the game. He’s an overly articulate space gorilla with a a heavy penchant for BS-bravado and a bitchin’ ship that has been crafted to resemble his own likeness. With the general headlining the show, much of the voice acting is extremely good – even if the dialogue is mostly so-so.

Blast Factor: What you realize as you get into it is that The Penal Zone is really attempting to be a comedy vehicle more-so than it is a video game. The main problem for me was that I never quite felt like the comedy aspect of it ever got off of the ground. There is an onslaught of jokes, many of which are just not funny and yet very long-winded at the same time. This led to impatience for me, as I often just wanted to get to the point. The game does allow you to skip through all the jabber-jawwing, but it’s easy to miss important clues in doing so. You are faced with the painful choice of enduring bad dialogue or run the risk of severe frustration down the road.

Sam and Max will have to get a lot funnier to interest me in ‘The Devil’s Playhouse: Ep.2′.

In spite of all this, you do drive a really sweet car — a 1960 DeSoto Adventurer. Its usefulness is limited with the ability to teleport, however.

Apple proudly boasted on Thursday that their highly successful iTunes Store has passed Wal-Mart as the top music retailer in the US.

iTunes has sold over four billion songs to over 50 million customers since opening in 2003.

“We launched iTunes less than five years ago, and it has now become the number one music retailer in the world,” said Eddy Cue, Apple’s iTunes vice president. “We are thrilled, and would like to thank all of our customers for helping us reach this incredible milestone.”

The ranking comes from market research data from NPD Group’s MusicWatch survey that tracks consumer purchases. iTunes topped Wal-Mart based on their January and February 2008 sales figures, Apple said in a statement.

This is yet another blow to the hard copy, “old way of doing things” music shopping experience. And yet, it is has shown that legal music downloading can and does succeed in the US.