What, after five decades of sticking mainly to standards, possessed Paul Anka to cover Duran Duran? As odd as this development may seem to long-time fans of the Ottawa crooner, it’s his swinging take on a slate of more contemporary tunes that has revitalized his career. His 2007 album Classic Songs, My Way—which reinterprets the work of Foreigner, Billy Joel and the Killers and mixes it with such much-loved Anka originals as the epochal title track—recently reached number two on the Canadian album chart. The author of hits for everyone from Frank Sinatra to Tom Jones knows a thing or two about what makes a good song.

It’s your golden anniversary year as a performer. How does it feel to have made it this far?
Heartwarming and somewhat cathartic. It takes the lid off a lot of things I wouldn’t normally look at. It brings me back to certain times in my life, and I wonder where the hell the time’s gone.

You’re working on a memoir, too. Why now?
I’ve been talking about doing this for years, but I’ve always said I’m waiting for a few people to die. Because I’ve been around so long, in the arenas that I’ve hung around in and the people I’ve hung out with, there’s so much stuff to write about. It’s just a question of figuring out how much I’m gonna tell.

Can we expect some juicy stories about Frank Sinatra?
There are a lot of things about the ’50s and ’60s that I think are important, and Sinatra is certainly one of them. So is Sammy Davis Jr. and many other performers, too. And people are fascinated with the environment of Vegas and the mob-driven situation there—they don’t really realize how deep it went.

On the new record, you sing duets with Michael Bublé and Jon Bon Jovi. How did you know Bon Jovi’s voice was right for “My Way”?
Jon is a great rock singer. He’s into that Sinatra thing, plus he’s Italian-American and has a feel for it. Here, his voice is allowed to flourish in a setting I don’t think he’s worked in before.

Speaking of stuff that hasn’t been done before, why Duran Duran’s “Ordinary World”?
The lyrics. A lot of those songs get lost in form-over-content issues, because they’re very particular to the group or the writer. But a good song is a good song. And we really stripped that one down—it’s very meaningful and fits me more as a ballad than any other vibe I could’ve put into it.

Paul Anka plays Massey Hall Dec. 4. $82.50–$135.50. 178 Victoria St., 416-872-4255, www.masseyhall.com.