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John Lennon went this week.  Paul McCartney a few months ago.  Led Zeppelin is on track for Thanksgiving.  The Beatles too are on the way.  Will Garth Brooks be the next of last major hold outs to come to iTunes?  Better yet, is an announcement about the country star’s catalog imminent?   …  The answers are probably and possibly (or at least, remotely possible).

There is no definitive or confirmed news yet, largely it’s conjecture, more iTunes speculation, but a few facts suggest the stars are beginning to align for Apple.  Notably, taken as a sum of the parts, there is evidence to suggest sooner than later, very possibly by November, Garth too will move from the minus to the plus column in Apple’s musical clubhouse.

Arguably, the biggest obstacle to Garth taking a bite out of Apple has been Wal-Mart.  Garth Brooks, it turns out, is a true rarity in the music business.  Not only has he sold a staggering 115+ million albums, he is also a rare artist that owns his own catalog and has no label affiliation.  In 2005, he both walked away from Capital Records and signed a deal giving Wal-Mart the exclusive distribution rights for his music (though he refused to allow them to sell his songs digitally).  That exclusivity has kept Apple and others from even entertaining hopes.

But now the Wal-Mart obstacle has been removed.  Last week Garth’s Pearl Records label announced it will begin to self distribute his catalog to the entire market.  No more exclusivity.  That makes for the first hint something could be coming. Hint number one.

The second hint: Garth is readying a new retrospective album.  Today and tomorrow, retailers and radio programmers have been invited to a Nashville presentation to preview a  new three-disc box set called the Ultimate Garth Brooks.  It is planned for a November release leaving several months for promotion (and deal making?) .

Billboard and Country Music Television have both reported that the album will have 34 tracks including four new songs and a companion video DVD.   New tracks are a big deal.  Garth formally retired in 2000 and said he was done recording. He also publicly vowed he would not tour at least until his youngest daughter graduated high school in 2015.  The new tracks are a reversal, and while a big tour is probably out of the question, Garth has loosened slightly from his performing stance too.  He’s done several live performances including one for a Hurricane Katrina benefit and the Live Earth concert in July. 

More than a talented singer and songwriter, but a  famed entertainer, someone with an amazing stage presence that hints at a true love for being on stage – its easy to speculate that the recent charity engagements may have rekindled his passion and left him itching to revisit the showmanship and craft he so clearly loves.   Hint number 3?

Further fuel for speculation: Led Zeppelin has a planned retrospective due in November. The Beatles catalog is expected to be done with remastering and available possibly by November as well (other speculation shoots for early 2008).  Garth Brooks would be the trifecta, the Triple Crown for Apple.  Unquestionably, there are people in Cupertino who’d love to connect those dots for that kind of announcement. 

Garth also has  kids in, or near, the iTunes–enabled age bracket.  It’s a safe bet they have iPods.  Maybe they’ve said “Daddy, its time to go digital.” Maybe they’ve convinced him.   Maybe a Garth iPod commercial would make the kids day. 

The last bit of information is the kicker.  Tomorrow, in Nashville, Garth himself has a called a press conference.  That’s hint number four.  Saturday, Garth speaks.

What he’ll talk about is unknown.  Maybe he’s called the conference only to talk about his new retrospective collection.  Maybe its promotional.  Maybe he’s going to use the opportunity to dispel speculation about iTunes, or a tour, or anything else remotely like this article. There isn’t, after all, much to tie him to Apple at this time.  Just speculation. Emerging Possibilities. Just conjecture.     Than again, on the other hand, a new album to promote and a press conference sure makes for a good opportunity to talk about what comes next, including the digital domain.  

We’ll have to wait and see but I’ll admit I have a  bias.   I’ve seen a lot of concerts, from arena shows to small clubs, from famed names to up and comers, Jazz to Rock to Country to Indie and back again.   Once, I saw Garth Brooks perform.  I went begrudgingly, expecting boredom, instead, I was so entertained that a decade later,  I’d proudly wait in line to see him perform again.   His show was the kind of live performance you talked about the next day even if you hated his music.  It was that much of a spectacle.  It was showmanship on the highest level, a real musical extravaganza.  

7 years of retirement, maybe he’s ready for a revival.  Maybe iTunes?  Something’s coming.  We’ll see soon enough what it is.

Update: Garth has held his press conference and the news is out. No tour is in the works (for now) and no iTunes or downloads just yet. Garth will be releasing a new single this month and his latest retrospective collection is on track for November, but digital pricing remains a hang up for him. The “Ultimate Hits” album will release at a discounted price point of around $11 to $14 and include 33 or 34 song tracks (including several new singles). If sold online and priced with the fixed iTunes pricing model, 99cents per song, he feels it isn’t a good buy for his fans. Explaining the logic, he said, “If you want to go online — if you want to pay 99 cents [per track] for all of them — at 33 bucks, the math’s pretty easy.” There’s still hope for album-only pricing or a digital offering down the road, however.