In the 50 years that Peter Asher has been involved in the entertainment industry, he's worn every hat imaginable -- from child actor in his native England to artist as one-half of the '60s duo Peter and Gordon, he later transitioned to A&R man at the Beatles' Apple Records, then manager (James Taylor), producer (Linda Rondstadt), major label executive (he was a senior vp at Sony Music from 1995 to 2001), and, most recently, back to management again (Asher was named co-president of Sanctuary Group in 2001, a post he left five years later).

So it should be little surprise that his latest career move would be nothing short of extraordinary: the 66-year-old is returning to the stage with a one-man show.

"Peter Asher: A Musical Memoir of the 60s and Beyond" is a multimedia experience that mixes video clips, photos and storytelling from Asher's illustrious history. It's scheduled for three inaugural performances, the first this Friday at New York City's Iridium, the next on Sunday, Dec. 5 at the Coach House in San Juan Capistrano and at L.A.'s Grammy Museum on Dec. 7, after which Asher will continue onto another of his passion projects: a tribute to Buddy Holly featuring reinterpretations of classic songs by the likes of Jackson Browne ("True Love Ways"), Jeff Lynne ("Words of Love"), Stevie Nicks ("Not Fade Away"), Cobra Starship ("Peggy Sue") and Fall Out Boy's Patrick Stump ("Everyday").

THR spoke with the accomplished music man on the day the Beatles iTunes announcement was made. Among the topics covered: the lengthy Apple v. Apple litigation, which he says seems "silly" in retrospect, but also "not a mistake."

Where did the idea for the show originate?

I've done a few keynote speeches and lectures that seemed to go very well. People were interested and asked a lot of questions, some would say, "How cool, we haven't heard that story before," so it was fun. Then when Gordon tragically died [in 2009], and I realized there would never be another Peter and Gordon show, I didn't want to give up on singing some of those songs or singing at all for that matter, so I had this idea for a mixture of hazy memories, storytelling, some multimedia, video clips, photos, reminiscences, plus some songs and call it a Memoir of the 60s and Beyond for want of a better title. We tried it out in Edmonton, Canada, where people really seemed to like it, so I was encouraged and thought, "What the hell? We'll do New York and L.A. and hope for the best."

How do you remember details from so long ago?

I don't. My particularly failing is dates. People always ask me, "How long were you at Apple? What year did you sign James Taylor?" I never know the answers. I have to look them up like anybody else. But I do remember how things felt, how they looked, what generally happened. I remember hearing certain songs for the first time. I remember James coming over to my house for the first time and playing for me. I remember these important key moments that were artistically and emotionally resonant at the time. And the good thing is that so much of this stuff is on the web now and dated. If I can't remember seeing Jimi Hendrix at the Saville Theatre for the first time, you just poke around online, find the damn poster and there it is, that's the date. So there's a lot you can check and wherever we can, we do.

The Beatles catalog is finally available digitally. Are you surprised it took this long?

It does seem silly, but it doesn't seem like a mistake. I know they had been talking forever, what suddenly made everything done, I don't know, but where people used to go, "How terrible that the Beatles haven't been on iTunes for so long." Now they're saying, "How cool that it hasn't been on iTunes this long?"

Do you think it was mainly the ongoing battle of using the name Apple?

That was part of it, of course, but I think there were bigger issues with Capitol, as I understand it.

What does it mean for the Beatles at this point in the band's legacy?

More money. [Laughs] Like everything in their career, it will turn out to be exactly right. Because the Beatles are so unbelievably good, whatever they do, like putting out CDs or going to iTunes way later than everybody else, appears to be a brilliant move. I remember when all the CDs suddenly hit the charts at the same time. Now I look at the iTunes chart, they're all over it. It just maintains the extraordinariness -- in the literal sense of the word -- of the Beatles. The regular rules don't apply to them at all.

In the music business, it's not uncommon for British executives to come work in the U.S., but bringing an American A&R man to England seems like it's rarely done. As someone who's worked on this side of the pond for a long time, do you see a disconnect between British and American taste?

I don't know about a disconnect, but there is a difference. I think the answer is probably less between any two people regardless of nationality. In other words, musical tastes vary enormously. Now, of course, as an A&R person, to some extent you're trying to guess what the nation's taste is going to be. Perhaps if you haven't lived in America or haven't been talking to American fans, or listening to American radio, you might not know that. It's very interesting. Traditionally, and this goes back to the old days when we started Apple, we brought in Ron Kass to be head of the label because we thought we wanted a proper American record man to be the boss, but it was never our intention for him to have anything to do with who we signed -- we wanted him to apply American business savoir faire and get-up-and-go marketing techniques. But we never thought he'll be the ripest to pick the act, so maybe it's an old prejudice and an old phenomena.

Looking back, the A&R-ing at Apple seemed way ahead of its time. Was that partly to blame for the label's downfall?

I think there are all kinds of reasons Apple folded in the end. It was stuff within the band, it was Magic Alex's bogus inventions -- but actually the record company on its own probably had about the same success-to-failure ratio as most record labels.

You're equally passionate about the music of Buddy Holly. Tell us about the tribute album you're putting together.

I am a huge fan. Buddy Holly was one of the things that brought Gordon and I together at school, back in the very formation of Peter and Gordon. I was more of a folkie, Gordon was more of a rocker and he pretty much taught me about Buddy Holly. Those songs always meant a lot to me, so when I was approached to take on the production of a Buddy Holly tribute for the 50th anniversary of his death, I was happy to do so. We've done seven tracks so far: Stevie Nicks, Lyle Lovett, Jeff Lynne who produced his own version of "Words of Love," which is brilliant, the Fray, Chris Isaac .... Who have I left out?

Cobra Starship, featuring your daughter Victoria on keytar!

Yes, they did "Peggy Sue." It was great was fun working with them in the studio and it's a cool version, if I do say so myself. The amazing thing about Buddy Holly was that he was a brilliant record producer as well as a great songwriter. A lot of his records were very unconventional -- the drum parts, weird percussion like using a cardboard box, all that kind of tippy-tappy stuff he did ... quite spare, but also very imaginative, cool stuff. So we tried to apply some of that philosophy.

And you're producing every track?

So far, the only one I didn't do is Jeff Lynne because he does all his stuff in his own studio, his own way. So I was happy spectator and visitor, but everything else has been tracked in L.A. at Conway Studios.

When do you hope to have it out and who will release it?

I'd like to see it come out in late spring. It may be a direct-to-retail deal, it's still a bit up in the air.

Are you still managing any artists?

Yes, I manage the Webb Sisters, two girls that I love dearly who are singing with Leonard Cohen at the moment and are releasing an album in the States early next year. I've been doing things more on a project-to-project basis, and spending a lot of time in the studio, but I don't have a full-on management operation at the moment. I would plunge back into it given the right circumstance. If the next James Taylor walked in, I would probably get just as excited as I did last time but it hasn't happened yet.