It’s of those eternal questions of the computing world that never seems to get answered definitively: Does the “Mac Tax” really exist? Some folks are positive that Macs are overpriced compared to Windows computers; others deny it steadfastly. Almost nobody, however, bothers to do the math in any serious detail.

So that’s what I’m going to do. And since Apple manufactures multiple models, I’m going to do it one computer at a time, starting with the MacBook, the company’s consumer notebook.

First, a mini-FAQ on this project:

Q. I see Windows notebooks for $500 everywhere. There are no $500 Mac notebooks–that proves Macs are more expensive.

A. Um, that isn’t a question, but yes, the cheapest Windows machines are cheaper than the cheapest Macs, and probably always will be. But the most expensive Windows PCs also cost more than the priciest Macs; there’s simply a far wider range of Windows computers out there. That’s a point in the favor of Windows systems for sure, since variety is good and some folks want a very basic machine at a very basic price. And it’s true that the average selling price for Windows boxes is around half the average price of Macs. But the only logical way to compare prices is to do so for roughly comparable systems. That’s what I’ve done here.

Q. How did you do your research?

A. I chose a standard MacBook configuration–the middle one, which is neither stripped down nor high-end…

Then I configured laptops as similarly as possible from the country’s two largest PC manufacturers (HP and Dell) and one which, like Apple, is associated with sexy-but-not-dirt-cheap machines (Sony).

The Dell was the XPS M1330…

The HP was the Pavilion dv4t…

…and the Sony was the VAIO VGN-SR190.

I did all my shopping at the manufacturers’ sites, since they all provide extensive tools for custom configurations, letting me pick machines that were as close as possible in specs.

Q. How do you take into account the fact that OS X is so obviously superior to Windows Vista?

A. I muse about how the operating systems compare a bit towards the end of this article, but I didn’t factor the question into my overall conclusions, since this is a price comparison, not an attempt to answer the overarching question of which platform is better. I also considered only purchase price, not overall cost of ownership. (You might make a case that Macs are cheaper to own than PCs simply because you spend less time worrying about spyware, adware, and junkware.)

Q. How do you take into account the fact that OS X is so obviously crummy as a gaming platform, or the fact that I can’t run my favorite accounting software on it?

A. See above answer. Whether a Mac is a good gaming or business PC is a different question from whether it’s cheap, pricey, or somewhere in between.

Q. Will you tell me which of the four machines I should buy?

A. Nope, this isn’t a review–I did no hands on testing or speed benchmarking.

Q. Are you going to make me read this entire article to learn whether the MacBook is expensive?

A. Oh, all right, here’s an executive summary: It’s in the same zone as the Dell and HP, while the Sony is around $300 more. If Macs are overpriced, the MacBook isn’t very good proof.

Q. Will you get on with your conclusions, already?

A. Sure–just click on to the next page.

(UPDATE: I answer even more questions about this project in this post.)

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I started to put together this video timeline starting in the 1970s and working my way forward to the present day. Then I realized that it’s more fun–and much bloggier–to begin with current commercials and travel backwards in time. Join me, won’t you?

iPhone (2008): If you’re discussing Apple ads in 2008, you gotta begin with an iPhone one. Here’s “Unslow,” which I’ve already written about in excessive detail.

MacBook Pro (2007): I have mixed feelings about the “Get a Mac” campaign–the best ones are very funny, and John Hodgman is a gem. But sometimes their portrait of the PC–as a machine that’s mostly good at spreadsheets–feels like it hasn’t been updated since, oh, 1992 or thereabouts. I do, however, confess that I was tickled to no end when PC called my former employer, PC World, to complain about one of our articles. (Fun fact: A second ad that mentioned PCW was made at the same time, but shown on network TV only one evening before Apple decided to kill it–I’ve never seen it.)

iPod Touch (2007): Gazillions of Apple fans have uploaded homemade ads to YouTube. Nick Haley is the only one whose creation went on to become a real Apple ad. This is Nick’s version, but Apple’s is nearly  identical.

iPod Nano (2007): With its use of multiple Nanos in different colors, this ad for the current-generation Nano feels like it’s practically an explicit homage to ads for the multicolored original iMacs. Music by Feist–not to be confused with Ellen Feiss.

iPod (2005): Apple pulled its iPod ad with Eminem from the airwaves almost instantly–maybe because footwear manufacturer Lugz complained that it was eerily similar to a commercial it had released in 2002. Here’s a mashup that a YouTube user spliced together, mixing bits and pieces of both ads almost seamlessly.

PowerBooks (2003): This ad for Apple’s portables remains entertaining, but mostly, it makes me nostalgic for the 12-inch PowerBook, a computer I thoroughly enjoyed owning. If Apple made something comparable today with an Intel chip inside, I’d buy it in a heartbeat.

“Desklamp” iMac (2002): I never owned one (or, come to think of it, any desktop Mac), but I loved the design of the second-generation iMac. It had a sense of humor, and I can’t think of another computer, Apple or otherwise, that I’d say that about. Apparently, though, it didn’t sell all that well, panache and clever ads notwithstanding.

Switch (2002): When this ad campaign premiered, trying to convince the teeming masses to dump their Windows boxes for Macs was a more idiosyncratic, unlikely quest than it became by the time the later “Get a Mac” commercials debuted. The most famous of the “Switch” ads featured teenager Ellen Feiss–this particular commercial is a follow-up to that one, and supposedly never aired. (Fun fact: I went to the same high school as Ellen, two decades earlier; back in my day, we used Radio Shack TRS-80s.)

iPod (c. 2001): Is this ad really from only seven years or so ago? The guy is goofy, the iMac looks retro, and even though it, like iPod ads to come, shows someone rocking out, it also feels obligated to try and explain the benefits of digital music. Eventually, iPod ads would become lifestyle celebrationse that assumed you knew what they were for, but this one is about a early-adopter gadget and why you might want it.

Power Mac G4 Cube (2000): When folks bring up the Cube–the only famous flop of Steve Jobs’ second Apple tenure–I always admit, in the interest of full disclosure, that I drank the Kool-Aid and gave it a good review in PC World. It had its issues as a workaday computing device (it was hard to get at the CD drive without shutting the machine off), but this much is undeniable: It looked fantastic in TV commercials.

Original iMac (1999): These days, so few computers are beige that it’s been years since I had reason to use the phrase “beige box.” When the original iMac debuted, though, the notion of a colorful computer was new and divisive: Some people bought the original iMac because they came in colors, while others spurned them for precisely the same reason. Here’s Jeff Goldblum, perhaps the last famous person to appear in an Apple ad as a more-or-less traditional pitchman.

Original iMac (1999): More Goldblum–in 1999, there were still people who were intimidated by e-mail and the Internet, and the original iMac was aimed at them.

Think Different (1997): The rational reaction to this ad, one of Apple’s most famous, is probably to scoff at its implicit comparison of people who buy a particular brand of computer to a collection of the last century’s greatest statesmen, artists, and scientific types. I gotta admit, though, that I find the ad moving. We Mac owners don’t deserve the comparison; Steve Jobs, in some ways at least, does. And this ad sure made clear that his return to Apple would not be business as usual. (Side note: The voiceover is by Richard Dreyfuss.)

Macintosh (c. 1995): It’s been an Apple tradition of surprisingly long standing to run both ads bashing Windows and one bragging that you can run it on a Mac. Here’s one from the Windows 95 era; it’s not specific about what means of putting Windows on a Mac it’s talking about, and I’ve forgotten what it was. (It’s not unreasonable to say that Boot Camp, Parallels, and VMware Fusion are the first means of running a Microsoft operating system on an Apple computer which are actually worth bothering with.)

Macintosh (c. mid 1990s): I’m not sure exactly when this Mac ad dates from, but it apparently comes from a forgotten age in which the Internet didn’t revolve around the Web (I do see Netscape Navigator briefly, tucked behind another window) but schools effortlessly streamed full-motion video over the Net.

Performa (c. mid 1990s): I include this commercial–dating from an era in which some Apple ads were still dedicated to simply explaining what a home computer could do–mostly because it includes a glimpse of eWorld, the short-lived Apple online service which is so obscure that nobody even bothers to make fun of it.

Power Macintosh (c. 1994): This ad was produced at a time when a bald guy in a suit was still visual shorthand for “important businessperson,” the After Dark screensaver was ubiquitous, and a Mr. Potato Head signaled wacky rebellion from corporate tradition. It was also a period in which Macs were so bedraggled that the only claim it appears to make about them is that they can read DOS floppies–which is just plain sad.

Newton (c. 1993): The comparison between the Newton and the iPhone has been made so many times that it’s incredibly trite–but it’s impossible to watch this Newton ad without thinking about it.

PowerBook Duo (1992): Many Apple innovations have had lasting impact on the computer industry. The idea of sliding a laptop into a desktop case like a giant VCR tape, however, did not.

PowerBook (c. early 1990s): The first Mac notebook ad involving a basketball player on an airplane–the great Kareem Abdul Jabbar.

PowerBook (c. early 1990s): I include this ad in part because “What’s on Your PowerBook” ranks among the better-known Apple campaigns–but also because the buttoned-down, bespectacled guy bragging about the mundane business applications he runs on his Mac (“org charts!”) is practically a proto-John Hodgman, except he’s arguing that Macs can be just as boring as PCs. Note also that the Internet only comes up in passing when he mentions e-mail, pegging this as an early-1990s commercial rather than a mid-1990s one.

Macintosh (c. 1990): After “1984,” Mac ads got incredibly tedious for years–in the Sculley era, they were full of guys in pinstriped shirts standing in anonymous offices discussing ROI. It’s as if Apple’s primary goal was to convince the world that Macs were just as lacking in personality as PCs. This is an ad of that sort, but it’s not bad, and it makes me nostalgic for the days of “portrait” displays.

Mac Portable (c. 1989): The Mac Portable was ungainly, illegible, and unaffordable ($6500), but Apple managed to make it look pretty appealing in this commercial. Note that in the late 1980s, it was still logical to address an ad for a pricey computer at people who weren’t very comfortable with computers. Also, setting the ad in an airplane terminal associated it with flying without showing someone trying to use this behemoth aboard a plane.

Apple IIgs (c. 1986): Here’s minimalism for you–this ad for the last iteration of the Apple II line makes no claims for the machine other than that it can be used to do homework.

Macintosh (1980s): This ad from Australia sports elaborate special effects, at least for a 1980s Apple commercial. In Australia, as in the U.S., wearing half-glasses is a sign of fabulous business success.

Macintosh (c. 1984): Twenty-four years ago, bitmapped fonts were kind of dazzling–even in blocky black-and-white–and Apple saved the exotic input device known as the mouse for the grand finale.

Macintosh (1984): Sorry to be sacrilegious–this ad, directed by Ridley Scott, has been called the best TV commercial of all time, but I’m not even sure if it’s ony of my ten favorite Apple spots. (I dunno–maybe it’s the utter lack of humor.) 1984 may not have turned out to be like 1984, but those IBM-using lemmings only grew in number in subsequent years, while the Mac struggled.

Apple IIc (c. 1984): In 1984, laptops as we later came to know them didn’t exist yet, and you could market a fairly svelte desktop (although I don’t think that term existed yet) as a sort of portable computer. I’m not sure how Apple got away with the image of a CRT monitor disappearing into the carrying case, though.

Apple II (c. 1981): As far as recall, Dick Cavett was the first celeb to do Apple ads, years before Jeff Goldblum, Eminem, and Mahatma Gandhi. Unlike those guys, he donned a jacket and tie for the occasion. For all the radical differences in Apple ads circa 1981 and circa 2008, they’re consistent in some ways: The voiceover performer in current iPhone ads has an urbane vibe that’s not unlike Cavett’s, as do multiple other narrators of Apple ads over the years.

Apple II (c. 1978): This ad, the earliest Apple-related one I can find, is from some local (Los Angeles-based?) an Oklahoma City computer dealer, not Apple itself–and even in 1978, its cheapo aesthetics probably gave Steve Jobs the heebie-jeebies. I think it’s kinda adorable, though, and I’m glad that somebody bothered to upload it to YouTube. The family that Pongs together belongs together!

Okay, which Apple ads did I ignore that I should have included? Are my takes on any of the ones I did include off-base? Lemme know what you think…and if it turns out that enough people are as obssessed with old computer ads as I am, I may round up more of ‘em.

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For a dozen years or so now, the Internet has been a mainstream communications medium, and its history has been pockmarked with examples of big-time services choking for extended periods–often a lot longer than today’s Gmail blip. The most famous examples of unplanned downtime have a lot in common: They usually last longer than anyone expected and get blamed on cryptic technical glitches. Almost always, angry consumers announce they’re done with the service in question; almost always, the service eventually recovers.

Oh, and one more thing: The biggest and most embarrassing failures all seem to happen during the summer months. Maybe technology, like human beings, just doesn’t work quite as hard when the weather’s hot and there are distractions like baseball games, picnics, and vacations to contemplate.

Now that Gmail’s back, it’s worth recapping a few other outages that made headlines when they happened–and since the ones that follow are in alphabetical order, they begin with maybe the most famous one of all (hint: it involved a company whose initials are A.O.L.)…

Who? America Online, the company that was synonymous with online services in the mid-1990s.
When? August 1996.
How long? 19 hours.
Why? AOL CEO Steve case blamed it on problems with the installation of “”high capacity switches within the local area network.“
Upshot? The service’s 6.3 million users received refunds for the downtime.
Saving grace? Steve Case’s artful and honest work as chief apologist made him even more famous as AOL’s public face.
Any other problems? AOL suffered multiple embarrassing outages in the era (here’s another one), then pretty much got over having ‘em–though a 5-hour e-mail meltdown in 2006 felt like old times all over again.

Who? eBay, then as now the world’s biggest auction site.
When? June 1998.
How long? Almost a day–reportedly the biggest outage in online history at the time.

Why? “[The] problem resulted from a failure in the software that was used to list items for sale and update bids. He insisted it was not a problem with the site being strained to capacity and said it was not clear why it had failed.” Matters were complicated further by the fact that eBay hadn’t quite finished implementing a backup system.
Upshot? eBay lost an estimated $3-$5 million in sales and was forced to offer refunds, extend auctions, and waive fees by way of apology to sellers whose auctions were affected.
Saving grace? Some eBay users who had bid early on items in auctions that were scheduled to end during the time the service turned out to be down got bargains.
Any other problems? This outage was one of several catastrophic ones that eBay suffered in 1998 and 1999.

Who? MobileMe, Apple’s brand-new service for synching information on iPhones, Macs, and PCs.
When? July 2008
How long? Several weeks of at least sporadic issues for some users.
Why? Apple’s MobileMe blog mentioned multiple technical gremlins, including “a lot more traffic to our servers than we anticipated,” a bug “that was preventing MobileMe IMAP mail folders from syncing correctly between the web app and Mac OS X Mail or Outlook,” and “a serious problem with one of our mail servers.”
Upshot? Apple extended all MobileMe accounts by a month; Steve Jobs said that the MobileMe launch wasn’t “up to Apple’s standards” in a widely-published internal memo and put a new Apple exec in charge of the service.
Saving grace? None to date, although it’s been a rare opportunity to see Apple eat crow.
Any other problems? As I write this, it appears that the worst of MobileMe’s woes may behind it, but grumbling continues; on June 29th, an Apple blog post promised an update later in the week, but none have been published.

Who? MSN Messenger, the instant-messaging service from the world’s largest software company.
When? July 2001.
How long? For some users, about a week.
Why? “[An] extremely rare set of circumstances occurred when one of our database servers had a disc controller fail.“
Upshot? Some unhappy users decamped to AIM, Yahoo Messenger, and other IM services.
Saving grace? The outage didn’t help people feel better about Microsoft’s scary HailStorm initiative for serving as a one-stop repository for all of consumers’ data and probably helped to kill it.
Any other problems? MSN Messenger also went down in 2003 and 2005.

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Dear Windows Vista,

First of all, I’m sorry it took me so long to sit down and write this letter. You’ve been an unusually busy operating system lately, starting with the official (if less than utterly final) demise of your predecessor Windows XP at the end of June. Then you spent some time helping with a Microsoft marketing experiment by pretending to be a new version Windows code-named “Mojave.” This week, however, seems to be a relatively quiet one for you–and so I wanted to take the opportunity to bend your ear.

We haven’t talked, but I’ve been watching you from afar and feeling your pain as you’ve dealt with more than your fair share of challenges. Eighteen months after your debut, you simply don’t have an aura of success about you. Worse, your aging predecessor, Windows XP, has unexpectedly gained armies of devotees who refuse to give it up. It’s a pretty sad state of affairs–your original marketing tagline may have been “The Wow Starts Now,” but many people remain steadfastly unwowed.

The idea behind Microsoft’s Mojave Experiment was to suggest that those who spurn you do so out of ignorance. It’s true that some Vista doubters base their distaste on what they’ve heard about you rather than hands-on experience. But I don’t know of anyone outside of Redmond who’d maintain that long-term exposure to you turns the average computer user into a raving fan. Sure, you’re better than you were when you first showed up, thanks to Service Pack 1 and improved compatibility with applications and peripherals. But I’ve talked to lots of people who have used you for many months, and while some of them are pleased with you there are plenty whose feelings range from ennui to anger.

Even Microsoft admits that you have a reputation as being a disappointment. The Mojave campaign sure implies that, as does the Vista site’s references to “confusion and lingering misunderstandings” about you. How often does any manufacturer of anything acknowledge unhappy customers at all?

So are you a disappointment, or is it all a bum rap? That question has at least two answers, depending on whether it’s about your sales or your quality. Let’s consider sales first.

Microsoft recently said that it had sold more than 180 million copies of you. That’s not chicken feed. But any real analysis of that number would need to be a pretty tricky math problem comparing it to XP’s sales at the equivalent time in its history, taking into account the number of the PCs in the world today vs. 2003. I haven’t seen Microsoft or anyone else undertake this in recent months.

I do know that when I worked at PC World, the percentage of our site visitors who used you was around half of the percentage that had adopted XP at the same point in its life. That can’t be good–surely the folks who visit a site called PCWorld.com are more likely to buy you than the average Joe, not less so. And in Technologizer’s brief life, we’ve received visits from three XP users for every one person who’s been running you. (Actually, for what it’s worth, we’ve had more visitors using OS X than you.)

Then there’s the question of just how many of the people who buy your licenses actually use you. This story from an Australian site has some Aussie HP execs saying that most of the businesses there who pay for you choose to use XP instead. How many of your 180 million sales fall into that category?

The bottom line is that you’re the current version of the operating system used on the vast majority of the world’s computers. If you hadn’t sold 180 million copies a year and a half after introduction, I’d have been startled. But I think only Microsoft has all the data needed to assess how you’re doing in comparison with their expectations previous to your release, and they haven’t revealed it.

Let’s move onto quality. Are you a terrible operating system? A disappointing one? A pretty good one? A gem? Is the Mojave message that you’re better than your reputation a reasonable take on things?

First the good news: I don’t think you’re terrible–when people ask me if they should avoid you when buying a new Windows PC, I recommend against doing so. That may not be a ringing endorsement, but it falls well short of the harshest possible take on you.

Your single biggest problem is that you fall so short of what people expected you to be. For 25 years, Microsoft has had a reputation for over-hyping upcoming products early and often–they even did it with your great-great-great-great-great grandfather, Windows 1.0, which was announced at Comdex two years before it shipped. They sure overhyped you, first by touting features that you didn’t end up having, such as WinFS, and then by claiming that using you would leave people saying “Wow”–or maybe leave them just plain speechless. Microsoft also egged people on to buy PCs that weren’t well-suited to running you, by creating the misleading “Windows Vista Capable” program that ended up being the subject of a class-action lawsuit.

In other words, your maker needlessly set expectations for you far too high. If they’d stuck to previewing features you actually had, avoided absurd claims about you, discouraged people from running you on underpowered PCs, and maybe even shipped you closer to the original schedule, you might have gotten a better reception–even if you were precisely the same operating system you ended up being.

You still would have caught flack, though. It’s not that you’re lacking in advantages; it’s more that most of them seem to come with downsides.

A few examples:

–You’re more secure, and that’s an important benefit–but your User Access Control is such a persistent pain in the neck that when I use you, I feel safer but unhappier.

–You signature feature is your Aero interface, a new look which mostly boils down to your window frames being semi-transparent. I’m not even going to address whether that’s a big enough whoop to consider adopting you–I’ll just note that the $1000 “Vista Capable” computer I bought at the time of your release runs Aero…until it chokes on it and shuts it off without warning.

–While I like some of your new features and interface tweaks (such as your desktop search and non-cascading Start menu) you also have a fair amount of what seems to be change for change’s sake (like your approach to file navigation).

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1) Its primary function is to display a handsome glowing red jewel on your iPhone’s screen:

2) It sells on Apple’s App Store for $999.99, thereby explaining its name: I Am Rich:

(Okay, it does have one other feature: If you touch the “i” in the lower right-hand corner, you get “a secret mantra…[which] may help you to stay rich, healthy, and successful.” Unless Heinrich decides to hand out reviewer’s copies of I Am Rich, I may never learn what that mantra is.)

Heinrich, incidentally, also sells an iPhone calculator app which, at $4.99, most likely appeals to a wider, less well-heeled audience.

Apple’s policy for approving or rejecting iPhone apps has been a bit fuzzy: It keeps approving and unapproving Nullriver’s NetShare tethering utility, and pulled the seemingly innocuous Box Office movie info app. It seems possible that whatever person or automated system put I Am Rich on the App Store was asleep at the proverbial wheel. But if I it stays up–and I have to confess that the jokester in me kinda-sorta hopes it does–one thing’s clear: Practical jokes are acceptable.

At first, all this reminded me of the days when lots of wiseacres put stuff on eBay ranging from babies to kidneys to pieces of space station Mir to their own souls. The auctions sometimes got bids in the thousands, tens of thousands, or millions of dollars; eBay tended to look askance at such hijinks, and shut down the sales as quickly as it could. But those auctions differed from Heinrich’s offering in at least two crucial ways: The items in question were usually illegal or impossible to sell, and  “bids” were clearly pranks that eBay would never have enforced.

Heinrich’s app. on the other hand, is real and seemingly clearly explained, and the App Store presumably automatically charges your credit card once you agree to buy it. Wonder if anyone who isn’t rich has been silly and/or bold enough to make the purchase?

(Via Daring Fireball’s John Gruber on Twitter.)

Further thought: Other than me, most of the people who are blogging about this seem to think it’s an obnoxious travesty, and possibly insulting to iPhone developers who are trying to sell real apps. The non-jokester in me see the point. Betcha it gets pulled down–if nothing else, the hassle of dealing with anyone who “accidentally” buys it isn’t worth the pain for Apple…and neither is the distraction from all the useful, worth-the-money iPhone apps out there.

Further further thought @ 8:19pm: Hey, let’s conduct a poll!

Further further thought @ 4:26pm on 8/6: I Am Rich is now missing from the App Store. Big surprise!

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But for every site that’s been lucky enough to have a long and happy existence, there have been countless ones whose lives were cut short. Sometimes their deaths were huge stories; sometimes they quietly fizzled away. And even though many of their untimely passings were self-inflicted, it’s still worth celebrating the fact that they existed at all.

Here, then, are quick tributes to ten sites that deserved to live longer than they did. My selection process was highly scientific: I compiled my list by thinking over which ones I missed most, and by asking some friends for their input. I tried to stick to ones that didn’t do themselves in by eventually becoming lousy or irrelevant. (That’s why F*cked Company isn’t here–that particular dot-com scandal sheet started out good, then became fetid, then became a ghost town.)

My list of sites that didn’t deserve to die is almost certainly different than yours–it would be pretty startling if were exactly the same, at least. So once you’ve read my picks, why not nominate some of your own in the comments?

My.MP3.com (January-May 2000)
What it was: An online service (part of Michael Robertson’s MP3.com) that let you listen to streaming music from anywhere, once you had proved you owned the CDs in question by inserting them in your PC’s CD drive.

What its loss was tragic: My.MP3.com made it really easy to enjoy all the music you owned, from anywhere you could get an Internet connection. Regardless of what the music industry thought of it–more on that in a moment–you’d have had to have a severe complex to feel guilty about enjoying music you’d paid for in the form of CDs.

On the other hand: You could only listen to a streaming version of a CD if MP3.com had ripped it –and while its library was extensive, it wasn’t all-encompassing.

Where it went: There have been multiple examples of the music industry putting the kibosh on innovative online services over copyright issues, but the rise, fall, and death of My.MP3.com happened with a speed that’s still breathtaking. On January 12th, the service went online. On January 24th, the Recording Industry Association of America sued MP3.com over it. In April, the RIAA won, and in May the service went online. MP3.com lived on, and even tried to revive My.MP3.com in legal form. But it was never the same. Oddly enough, MP3.com ended up being acquired by a big music company–Universal Vivendi–that ended up killing it; the current CNET site at that domain is unrelated to the original one except in name,

Adequate substitutes: I’m not sure if there is one–at least not one that’s both legal and as simple as My.Mp3.com. But software such as Simplify Media will let you stream MP3s you’ve burned from CDs across the Internet, which accomplishes something similar, albeit in a less effortless way.

HotBot (1996-present, but only sort of)
What it was: A search engine from Wired Digital, the online arm of Wired magazine, which was powered by Inktomi’s search technology.

Why its loss was tragic: For its time, HotBot was a remarkably fast, relevant search engine compared to AltaVista and other contenders–and hey, it had a cool name. It felt like the first second-generation search engine. Upshot: There was a time when it was the favorite search tool of many discerning people (such as…well, me).

On the other hand: I can’t think of anything bad to say about HotBot in its prime.

Where it went: In 1998, Wired Digital was acquired by Lycos, which stopped investing in it just as other search engines started to improve in quality by leaps and bounds. Before long, HotBot served as a good example of how a hip, innovative site can become a forgotten laggard in very little time. (Come to think of it, Lycos itself ended up proving the same point.) In a technical sense, HotBot still exists–you can go to HotBot.com and search the Web. But it’s just a prosaic front end for Yahoo, LyGO (who?), and MSN. It makes me a little sad to see the once-beloved site in its current state.

Adequate substitutes: Here’s a useful newcomer among search engines you may like.

Webvan (1999-2001)
What it was: A wildly ambitious online grocer, cofounded by Louis Borders of the bookstore chain that bears his name; at its height, it delivered in ten major cities.

Why its loss was tragic: I confess that I’ve never ordered so much as a tin of deviled ham online. But I have friends who still get a little emotional when the subject of Webvan comes up–they loved it that much, and can still describe produce they received from it close to a decade ago. At least some of these folks haven’t bonded with any other online grocer since.

On the other hand: Webvan wasn’t perfect–despite the millions it invested in infrastructure and technology, it ran out of Thanksgiving foodstuffs in 2000 and its Website couldn’t handle the onslaught of turkey hunters. And when it went out of business, it blamed its demise in part on declining volume of orders, which would seem to indicate that not everyone who tried it loved it.

Where it went: Webvan poured hundreds of millions of dollars into huge, state-of-the-art warehouses, but never got enough business to make the investment pay off; the public company’s stock, once worth $34, fell to six cents. In 2001, it was forced to close up shop, selling off its real estate, technology, and hundreds of Aeron chairs, and donating unsed food to charity.

Adequate substitutes: Peapod, which predates Webvan, is still delivering on the east coast and in the midwest; major brick-and-mortar grocers like Safeway and Albertson’s do online delivery. But seven years after Webvan collapsed, the vast majority of grocery shopping is still done the old fashioned way, by trudging around a supermarket with a cart.

The Secret Diary of Steve Jobs (2006-2008)
What it was: An anonymous (at first ) blog written in the voice of Apple’s Steve Jobs, which was profane, mean, funny, and wildly imaginative–and which got better and better as Fake Steve developed into a character who was distinct from real Steve.

Why its loss was tragic: Few blogs have ever been as clever as Fake Steve Jobs at its best; few games have ever been as entertaining as trying to figure out who wrote it.

On the other hand: For months, people kept thinking they’d figured out who Fake Steve was, but getting it wrong. But on August 5th, 2007, New York Times Brad Stone correctly identified FSJ as actually being Forbes reporter Dan Lyons. The blog went on and remained inventive and amusing, but the end of the guessing game inevitably took some of the zing out of it.

Where it went: On July 9th, 2008, Lyons–er, Fake Steve–wrote a farewell post. The real Dan Lyons, who had recently left Forbes for Newsweek, said he was ending the blog because of worries over Steve Jobs’ health and launched a new blog called, logically enough, Real Dan.

Adequate substitutes: Real Dan reads very much like Fake Steve, except for the unavoidable, unfortunate fact that he must refer to Steve Jobs in the third person. And the Fake Steve posts are still available at the original site as well as in a book.

Full disclosure: Fake Steve once blogged about me.

Productopia (1999-2000)
What it was: A site that set out to be the Consumer Reports of the Internet age, reviewing everything from cars and cameras to shaving cream and sunglasses.

Why its loss was tragic: Just because it was a promising site that did what it did well, with a punchy review format that rated everything on three factors: quality, style, and value. And then as now, Consumer Reports was one of the few sites on the Web that charged a membership fee; Productopia, which attempted to support itself with advertising, was free.

On the other hand: You could argue that on the Web, it’s smarter to get your product reviews from specialist sites such as Edmunds, Digital Camera Resource, TimeZone, and (free plug for my former employer) PC World than to go to one generalist site. It was impossible for Productopia to cover everything, especially since it tried to with evaluations by professionals on its staff, rather than cheap-but-useful content in the form of user reviews.

Where it went: Before the dot-com collapse, investors were giddy enough to give Productopia’s founders almost $22 million; those founders were equally giddy, as shown by moves such as spending $4 million for a huge ad campaign–which appeared only in New York and San Francisco. But Productopia closed after it had spent all its money and couldn’t get more; its 16 months of existence was brief even by dot-com disaster standards.

Adequate substitutes: ConsumerReports.org remains the gold standard in comprehensive reviews sites. Consumer Search–which is where you go if you try to go to Productopia.com these days–is a useful reviews aggregator. And when I’m shopping for something like a blender or an elliptical trainer, I always check out the surging sea of user reviews at Amazon.com.

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1) I worked for a large company that used Lotus Notes–as large companies are wont to do–and there was no good way to get Notes on an iPhone;

2) Every time I tried Mobile Safari, I got depressed by how hobbled such an excellent piece of software was by the slow AT&T EDGE data network;

3) I didn’t want to buy a phone that could only run the applications that Apple itself decided to produce.

Problem one went away when I departed the corporate world to start Technologizer. (Side note: I’ve been using Gmail and Google Calendar to do the stuff I used to do in Notes.) The iPhone 3G solved the second one. And with the advent of the Apple 2.0 software, the iPhone can run third-party applications, of which there are already hundreds in the iTunes Store. So last Friday, I got myself up at 2:30am and braved the lines to buy an iPhone 3G–and a week later, I’m mostly extremely pleased with it.

Already, the library of iPhone apps is impressive: I’ve been downloading and enjoying applications such as Twitterific and Facebook, and am giddy at the prospect of other cool programs to come. But I’m glum about the fact that there’s one major category of software that appears to simply not exist on the iPhone: Utiltiies that change the standard functionality of the phone’s operating system and built-in applications. There are tons of such programs for Windows Mobile, and I used a bunch of them on my Tilt to make it that much more personal.

As far as I can tell, the lack of such programs on the iPhone–the App Store does have a “Utilities” section, but it includes no true utilities–is intentional. When Apple’s explained the architecture of the phone as an application platform, it’s talked about how applications are sandboxed so as to limit the damage that a poorly-written program can do. You can’t both sandbox apps and let them dig into OS itself and change its functionality. That means that other developers can’t build the tweaking tools that are commonplace with Windows Mobile. And even in the iPhone 2.0 software, Apple provides only a handful of ways for users to customize the phone.

So right now, the iPhone interface is what it is. What it is is by far the best interface ever produced for a mobile device, but that doesn’t mean there aren’t lots of ways I’d change it if I could. Such as…

1. On my Tilt–and I know this is geeky and atypical–I’d programmed just about every button I could to do something that made the phone faster to use. (One press on a button normally used for Push to Talk brought up my calendar; two presses on it brought up my to-do list.) The iPhone, of course, has only one real button, and it takes you to the Home screen; Apple does let you configure it to take you to your phone Favorites or the iPod features if you press it twice. At the very least, I’d like to be able to specify that it launch any Apple or non-Apple app I choose when I press it twice. And hey, if you could configure it to do custom things if you pressed it three times–or, God help me, four times–I’d probably use that, too.

2) How about also being able to specify what the Home button does if you press it and hold it down for awhile?

3) Steve Jobs was so pleased with the iPhone’s “Slide to unlock” feature that it was just about the first thing he showed at the iPhone’s unveiling at Macworld Expo 2007. It is indeed a clever and useful feature. Despite that, I’d like the ability to turn it off, or to specify that the iPhone not need to be unlocked for a specific period after it first shuts itself off. Sliding to unlock feels a lot less cool when you do it dozens of times a day, as I’m doing now.

4) Here’s another goofy, geeky idea I’d use: What if you could set up multiple Slide-to-unlock sliders that took you to different apps?

5) Sticking with the iPhone’s behavior when you first turn it on for a moment, the customizable wallpaper is nice, but I wish I could skip the wallpaper and simply see whatever application I’m in before I slide to unlock. I’ve usually forgotten where I was, and it takes a millisecond or two for me to remember; I’d rather be reminded instantly.

6) Speaking of which, the app I was in last time I used the iPhone is often not the one I want to use when I turn it back on. If you could configure the phone to return to the Home screen rather than to the last app used, I might do that.

7) When you return to an app you’ve been out of for awhile, the iPhone takes you to wherever you were when you left–such as a particular inbox of one of your e-mail accounts. Which makes perfect sense, but if I could, I’d at least experiment with returning to the top-level screen of the app. (It can take a lot of thumbpresses to back your way out.)

8) There’s lots of opportunity to let uses program custom finger-swipes. What if you could launch a specific app or perform a certain task by swiping your finger quickly from to bottom–and another one by swiping from bottom to top?

9) I like the fact that you can move your program icons around on the Home screen, and that swiping your finger lets you jump to additional Home screens as needed. I’d be even happier if there was a way to set up Home screens for particular types of apps–say, one for productivity tools and another for games.

10) I don’t understand why the iPhone’s otherwise wonderful YouTube app, when I flip the phone into horizontal mode, doesn’t notice whether I’m holding the phone with the Home button on the left or right. It always shows up assuming that the Home button is on the right, but I always instinctively have it on the left, perhaps because I’m a lefty. Which means that YouTube is upside-down and I need to flip the phone around.

11) On the Tilt, I was stuck with Microsoft’s archaic Pocket Internet Explorer, but it was a lot less archaic once I installed a nifty utility called PiePlus which added most of the features that IE lacked. Safari doesn’t need help in the way that IE did, but I’d still like to see the ability for third-party developers to add features to it.

12) Once you’ve made a call with the iPhone, the on-screen keypad goes away until you bring it back with a press. I wish it could stay onscreen at all times during a call; there seems to be enough real estate to make that happen.

13)  One last wonky desire: If there were a Bluetooth keyboard for the iPhone that I could use instead of the onscreen one, I’d probably buy it. I’m not sure whether third-party developers have access to the iPhone’s Bluetooth, though…or whether they could suppress the on-screen keyboard when the real one was in use.

I could list another twenty things I’d love to see, and maybe I will at some point. My guess is that Apple will eventually implement a feature or two I mention above, and there are others that they’d absolutely, positively refuse to add. That’s their right. But it would be swell if independent iPhone developers made this amazing phone do just about anything that iPhone users wanted it to…

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