He's the son of a veterinarian, the oldest of four rambunctious siblings, and has been reading the Wall Street Journal since age 11, according to various online biographies. He grew up outside Philadelphia's Main Line, near both old money and Amish frugality. He got a degree in economics from the University of North Carolina, married his wife Lynne and took a job at Atlanta's second-largest global investment firm. He has written two books, hosts a local talk radio show, writes a column for the New York Daily News online, and runs a website filled with enthusiastic financial planning advice. (We counted a dozen exclamation points on his home page alone.)

But Wes Moss' main claim to fame, until now, was his stint on The Apprentice with Donald Trump. He was fired half-way through the second season for ceding control of a Levi jeans photo shoot to a woman who, in his words, "flew into the studio on her broomstick." In the boardroom Trump canned them both — the show's first double-firing. "I would have at least liked my own cab," Moss quipped on the way home.

Today he is the face of Microsoft's (MSFT) Zune digital music player and star of Redmond's latest Apple (AAPL) attack ad. As with the Laptop Hunter series, Microsoft goes directly for Apple's pecuniary jugular, stacking the cost of filling a 120GB iPod with songs purchased from the iTunes Store ($30,000) against the cost of a monthly Zune Pass subscription ($15).

"People worry about the capacity of their iPod," Moss says on screen. "What about the capacity of their bank account? At a buck a song, they'll run out of money way before they run out of space." (See video below.)

It's a catchy spot, delivered by Moss with plenty of exclamation points. But it's really an argument between two business models — à la carte vs. subscription — that the market has so far settled in Apple's favor.

And once again, there are holes in Microsoft's argument large enough to drive an army of Apple blogs. Here's Emil Protalinski's take on it in Ars Technica:

"So where does Microsoft get the $30,000 number? Well, seeing as the 120GB iPod appears in the ad, I'm thinking the company is estimating each song at about 4MB, which really isn't much of an exaggeration. Of course, it's not exactly $15 versus $30,000. The $15 is a monthly fee, so you're likely going to be paying more if you plan on playing music for more than a month. That said, it would take you 166 years and 8 months to shell out $30,000 for the Zune Pass; many of us won't be living that long.

"As of November 2008, the Zune Pass allows its users to keep any 10 songs per month. In other words, if you wanted 30,000 songs for keeps, just like the iTunes Store, you would have to wait 250 years. The cost would be a whopping $45,000, however. In other words, it's only really worth it if you're OK with the fact that you have to keep paying the monthly fee to keep access to the songs that you don't yet own. Otherwise, iTunes (or any other à la carte model) is the way to go."

Worth a visit: Moss' ZunePass MAX'D CALCULATOR. As you adjust the capacity of your iPod from 4GB to 120GB, the image changes, with swooshy sound effects, from tiny shuffle to big black classic. Cool.

See also:

• How Microsoft put Apple users on the defensive
• All about Microsoft’s ‘Lauren’
• Behind Microsoft’s ‘Apple tax’ gambit
• Is the Apple press falling into Microsoft’s trap?
• Apple slams Microsoft with rubber chickens

Below the fold: The Zune Pass ad, via YouTube.

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When Apple announced Tuesday that it was finally lifting the so-called digital rights management (DRM) restrictions that iTunes music customers found so onerous, it left one thing out: the cost of doing so — in money and, as we learned overnight, time.

“We are thrilled to be able to offer our iTunes customers DRM-free iTunes Plus songs in high quality audio," said Steve Jobs in a press release.

"It's really easy," said senior vice president Phil Schiller in his Macworld keynote address, "to go in and convert your entire music library" with one click.

He didn't mention that it would cost you 30 cents per song, 60 cents per music video, and 30% of the cost of an album to do it.

Leave it to Apple (AAPL) to turn the lifting of restrictions into a profit center. If users convert every one of the 6 billion songs purchased from the iTunes Store over the past six years, a rich new revenue stream will flow toward Cupertino. Techcrunch's Erick Schonfeld calls it a "$1.8 billion music tax."

Of course, not all of those 6 billion songs will be converted. Apple's DRM protection scheme made it difficult to move music from one computer to another, share it with friends or play it on a non-Apple music player, such as SanDisk's (SNDK) Sansa Fuze or Microsoft's (MSFT) Zune — restrictions that don't affect every iTunes customer.

Besides, as AppScout helpfully points out, you can still make your songs DRM-free by burning them on a disk and ripping them back into iTunes.

But the burn-and-rip process is cumbersome and wastes a lot of plastic, so we decided to try the Schiller one-click method.

The first thing we learned was that it's not quite as easy as he made it sound.

When I went to the iTunes store, the little "Upgrade My Library" button, which usually appears at the bottom of the Quick Links box in the upper right hand corner of the front page, was mysteriously missing.

It took some time to figure out why. If you have several iTunes accounts — as I do — you have to log in on the account you used to purchase your songs before you can convert them. (Note to Steve: Removing a button is not the best way to send this message to a user.)

When I finally situated myself in the proper account, the button appeared. I clicked it and held my breath. I have a lot of stuff in my music library — 4,579 songs, to be precise. Converting all that music could be prohibitively expensive.

As it turned out, the bulk of my songs had nothing to do with Apple. Most of them were copied legally from my — and my friends' — CD collections.

But 231 songs — consisting of 100 individual titles and 6 albums, according to iTunes — had been purchased from the Apple store and were eligible for conversion at a cost of $50.60.

OK. At 12:25 a.m. PST, I clicked and waited.

Seven hours later, I'm still waiting.

"Your iTunes Plus upgrade is now processing," my computer tells me. "When your iTunes Plus music is ready to begin downloading, you will receive an email with download instructions and other information about your upgrade."

Either a lot of people decided to convert their music Tuesday night, overburdening Apple's iTunes servers, or this is a more cumbersome process than I — or Phil Schiller — imagined.

UPDATE: Three days, six error messages, three phone calls to Apple, two intercessions by iTunes customer support and $109.47 later, I've successfully update all the copy-protected items in all my accounts — 473 songs and 14 albums. I think I may need a better sound system to hear the difference in audio quality.

"30 Rock," "The Wire" and "Battlestar Galactica" are among the TV shows honored in iTunes 2008, Apple's (AAPL) comprehensive — and surprisingly opinionated — year-end review. [iTunes link]

Available through what used to be called the iTunes Music Store, iTunes 2008 covers all the media the online venue now serves up: movies, TV, audiobooks, podcasts, iPhone apps and music in genres ranging from Alternative to World.

Most categories are represented by software-generated lists of top sellers — often a good way to find out what your kids are listening to or what you might be missing. The lists of free and paid iPhone Apps are particularly useful — and have been getting the most attention in the blogosphere (see here).

But who knew, for example, that videos of talks from the TED technology conferences, which cost $3,750 if you want to watch them live in Monterey or Palm Springs, are now available for free through iTunes? In 2008, TEDTalks were the No. 2 most popular podcasts in the Classics: Video slot.

In several categories, however, Apple has gone beyond simply publishing top-10 lists and started making judgments about which books or shows are not just popular, but worthy of our attention. Apparently, it's not enough that Apple delivers the lion's share of our digital content; now it wants to dictate our tastes as well.

This is not the first time Apple has offered opinions through iTunes; witness its regular "staff favorites" and "what we're watching" lists. But this is the first time the iTunes Store's editorial voice has come through quite so forcefully.

"Proof positive that TV can be literature," begins the 54-word review of "The Wire, Season 5," iTunes' choice for best drama of 2008. "Human tragedies and triumphs are always center stage."

Or see its thumbnail summary of the pilot for "Breaking Bad," iTunes' pick for best single episode in a dramatic series:

"Bryan Cranston's slow-burn descent into dealing crystal meth is less a guilty pleasure than a tragic look at the unexpected choices we have to make to support our families. Desperate measures, indeed."

Who writes this stuff? And what's next, Ebert & Roeper on Koi Pond and Lightsaber Unleashed?

Last we checked, the full catalog of Beatles songs was supposed to be available for sale on the iTunes Store before the end of 2008.

Well, it's not happening this year, according to one of the band's two surviving members, and for all we know it may never happen.

"The last word I got back was it's stalled at the whole moment, the whole process," Paul McCartney told reporters gathered Monday for the media launch of his latest album, Electric Arguments. (link)

Where's Fake Steve Jobs when we need him?

Nobody was better at cutting through the posturing, lawyering and stonewalling by Apple Inc. (AAPL), the Beatles' Apple Corps and EMI that have kept the world's best-selling musical act off the world's largest digital music store lo these many years. (EMI owns the rights to Beatles recordings, but must get permission from Apple Corps to release them in new formats.)

A year ago, McCartney told Billboard.com that the deal was all but signed. "The whole thing is primed, ready to go — there’s just maybe one little sticking point left, and I think it’s being cleared up as we speak, so it shouldn’t be too long. It’s down to fine-tuning.” (link)

"Let me put that statement into American English," Dan Lyons (a.k.a. Fake Steve Jobs) wrote at the time. "Paul wants more money." (link)

Now, a year later, the sticking points seem to have multiplied.

At Monday's press conference, Sir Paul was asked once again when the Beatles were coming to iTunes. Here, according to Billboard.biz, was his full reply:

"That is constantly being talked of, we'd like to do it," said McCartney. "What happens is, when something's as big as The Beatles, it's heavy negotiations.

"We are very for it, we've been pushing it. But there are a couple of sticking points, I understand. So the last word I got back was that it had stalled, the whole process.

"They [EMI] want something we're not prepared to give them. Hey, sounds like the music business.

"It's between EMI and The Beatles. What else is new." (link)

EMI, in response, issued this statement:

"We have been working hard to secure agreement with Apple Corps. to make the Beatles' legendary recording catalog available to fans in digital form. Unfortunately the various parties involved have been unable to reach agreement but we really hope everyone can make progress soon." (link)

Translation: Paul wants more money.

Or maybe Yoko Ono is the problem. One of the classic entries in the Secret Diary of Steve Jobs — before Lyons gave it up to write full-time for Newsweek (and before Newsweek finally muzzled the Real Dan Lyons) — was the scene in which he imagined Jobs and Yoko trying to thrash out an agreement in John Lennon's old apartment in Manhattan. (The deal falls apart on Yoko's insistence that the band be billed as  "John Lennon and the Beatles" with Yoko listed as the fifth Beatle.) (link)

The irony is that the parties involved have dragged their heels for so long that much of the deal's original value may have evaporated. Most everyone who cares about the Beatles has already filled their iPods with songs ripped from the CDs. Meanwhile, as Peter Kafka reports on All Things Digital, the boom in digital music sales seems to be slowing, which could make even the digital Beatles harder to sell. (link)

If Sir Paul is really waiting for a better offer, he — and the Beatles fans — could be waiting for a very long time.

[Photo: The Beatles' Feb. 7, 1964 New York press conference, courtesy of Apple Corps.]

One of the unintended consequences of the success of the iPhone is that it has rendered the classic iPod and its diminutive sisters — the nano and the shuffle — nearly irrelevant. What do you need a second MP3 player for if you've already got a few hundred tunes in your pocket?

Apple (AAPL) was able to goose sales for a while last spring by sharply cutting prices on the iPod shuffle, but the tide is drifting away from the company's iconic product — which once accounted for nearly 50% of its annual revenue. By last Christmas, sales of iPods, which enjoyed triple-digit growth as recently as 2006, had nearly flattened out. If something isn't done, they could soon be headed south.

Enter Steve Jobs, who is expected to appear in person at the Yerba Buena Center for the Performing Arts in San Francisco next Tuesday for a special media event entitled "Let's Rock." Jobs has made an annual ritual of introducing new iPods in September — giving the company plenty of time to ramp up for holiday sales. In 2005 the star of the show was the original iPod nano. Last year it was the iPod touch.

This year, according to several converging rumor threads, Jobs will introduce a brand new edition of the iPod nano, a slightly modified iPod touch and a jazzed up version of the iTunes software that feeds content to them both. The details:

• iPod nano. Adding to — and correcting — last week's rumor of an iPod nano with a long, curved screen, iLounge on Wednesday released blueprint-like specifications for what it claims is the new nano. The specs suggest that this will be the longest and skinniest iPod yet. A new image carried by MacRumors Thursday appears to show the same device.
• iPod touch. iLounge also published blueprints for the iPod touch, which seems to be getting a more modest redesign to bring it (and its manufacturing processes) more in line with the iPhone 3G. The device is also rumored to be due for a simultaneous memory upgrade and price cut to bring the $299 8 gig iPod touch more in line with the $199 8 gig iPhone 3G.
• iTunes 8. According to Digg's Kevin Rose — whose credibility as an Apple prognosticator rose after he correctly predicted the date of the Sept. 9 event (see Apple's Fall product lineup) — iTunes is set for a "big update" that includes a Pandora-like music recommendation engine and new tools to let users download HD versions of their favorite TV shows and sync them to selected iPods (specifically, the 4th generation nano, the 2nd generation classic and the 2nd generation touch). [See below the fold for a guide to the various generations of iPods.]

Will these changes be enough to bring back the days of double- or triple-digit sales growth? Probably not. But if the price cuts are steep enough and there are enough new and interesting things you can do with iPods — like download applications from the App Store — the latest versions could find their way onto Christmas wish lists for a few more years.

Below the fold: A taxonomy of iPods, past and present:

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Apple issued two nice round numbers on Thursday.

First, it announced that the number of songs purchased and downloaded from the iTunes store since it opened on April 28, 2003 has passed the 5 billion mark. This represents a continued acceleration of music sales. It took Apple (AAPL) nearly three years to sell its first billion songs (Feb 23, 2006), ten months to sell its second billion (Jan. 6, 2007), seven months to sell its third (July 31, 2007) five and a half to sell its fourth (Jan. 15, 2008), and five months to sell its fifth (June 19, 2008).

It's harder to put Apple's second announcement — that movies are now being purchased or rented from the iTunes store at the rate of more than 50,000 a day — in perspective. Apple has been selling videos since 2005, but at first those were strictly music videos and TV shows. Movies came later, mostly from Disney. By April 2007, Apple was able to announce that it had sold more than 2 million movies. Movie rentals didn't start until January of this year, when Hollywood finally opened its film vaults, but it's probably fair to assume that rentals represent the larger part of the more than 50,000 titles being downloaded every day. At that rate, Apple is selling or renting 1.5 million movies a month and should have another nice round number for us by Macworld 2009.

Apple now claims that the iTunes store is the No. 1 music retailer in the U.S. and the world's most popular online movie store.

The company has never revealed how much money it makes on each song or video it delivers; it claims to run the iTunes store at "just above break even." Independent estimates put its profit margin on music sales at 10% to 30% percent.

No more ad-free episodes of The Office, 30 Rock, Scrubs or Friday Night Lights for $1.99 each.

As promised, NBC (GE) removed all its content and that of its affiliates from the iTunes Store over the weekend after its contract with Apple (AAPL) expired.

That means no shows on iTunes from Bravo, mun2, NBC, NBC News, CNBC, NBC Sports, Sci Fi, Sleuth, Telemundo or USA Network. (Some shows aired on NBC but produced by other Hollywood studios such as Viacom, Disney or 20th Century Fox are still available.)

NBC has put some of that content on NBC Direct, an ad-supported download service that runs only on Windows machines; a Mac version is due next year. Its shows will also be available on hulu.com, a joint venture with News Corp. Both services are still in beta.

NBC had been Apple's single largest partner for digital video, with more than 1,500 hours of programming representing either 30% or 40% of iTunes video content, depending which side you believe. Talks to renew the contract reached an impasse last August. NBC wanted to be able to charge more than $1.99 for its most popular shows. Apple insisted on a flat per-show rate and claimed that the network wanted to raise prices to as much as $4.99 per episode. (See Apple to NBC: Drop Dead.)

In a recent interview, NBC Universal CEO Jeff Zucker insisted its demands were "modest" and complained that Steve Jobs was undervaluing video content in order to sell more iPods.

“We don’t want to replace the dollars we were making in the analog world with pennies on the digital side,” he said, according to Variety.