What’s with Steve Paikin’s Frank Sinatra obsession?

The host of “The Agenda” explains his love of the Great American Songbook
By Daniel Kitts - Published on Dec 10, 2020
Ring-a-ding-ding. (Shutterstock/Kraft74)

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On Wednesday, The Agenda aired its annual music show — a TVO holiday tradition. This year’s edition featured a segment on Ruth Lowe, a Canadian who penned some of Frank Sinatra’s most popular songs.

This is a perfect guest for Steve Paikin, because Steve loves Frank Sinatra. I’ve worked at TVO for more than 20 years, and I’ve always found Steve’s taste for mid-century crooners such as Sinatra and Tony Bennett surprising. Not that there’s anything wrong with it: you’re never too young or too old to like a certain type of music. Still, it’s unusual for someone who grew up in the era of rock bands such as Led Zeppelin and Pink Floyd to be into tunes that were on the charts in the 1950s — or even earlier. So I called Steve up to talk about the roots of his taste in music.

TVO.org: How were you introduced to the music of Frank Sinatra?

Steve Paikin: My father. He certainly got me into jazz and the Great American Songbook — which would be Frank Sinatra, Tony Bennett, and all of that. And it basically made me a person who should not have been born in 1960 but rather in 1930 or 1940.

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TVO.org: Well, that's the thing I was wondering about, because usually someone your age is really into classic rock or pop music.

Steve: And I am.

TVO.org: You are, but it seems that the music of Sinatra and Tony Bennett speaks to you in a way that more recent music doesn't. Why is that?

Steve: It's an accurate observation on your part. I think the music that they sing from the so-called Great American Songbook does speak to me in a way that, obviously, louder, more rock-and-roll-type stuff does not. And I'm the least introspective person you know, Daniel, so I'm really not sure how to answer the question other than: I love the music because it's great. I love the music because Frank and Tony sing it, and they are legends. I love the music because it also connects me to my folks. I've seen Frank perform three times; I think I've seen Tony perform three or four times.

Man singing into a microphone
Frank Sinatra belts out a tune in Chicago on Sept. 10, 1986. (Shutterstock/Mark Reinstein)

TVO.org: What was it like to see Sinatra perform?

Steve: Everything you could imagine. It was like being transported back to the Rat Pack days of Las Vegas in the 1950s and ’60s — even though, when I saw him, he clearly wasn't the ring-a-ding-ding kid anymore. His voice might not have had quite the power and the range that it would have when he was younger. But it was still him. It was still Frank Sinatra — in my view, the greatest singer who ever lived.

TVO.org: Your father introduced you to the music of Sinatra. You have four kids. What do they think of Sinatra and Bennett?

Steve: They all know it. I'm sure it was a form of child abuse that I introduced them to it and forced them to listen to it. But they absolutely all know it — they all grew up with it. From the time they were a matter of hours old. As I was holding them in my arms, I was singing Frank's songs to them.

Frank Sinatra performs "I've Got You Under My Skin" in 1965.

TVO.org: Do they like it?

Steve: They say they do. And I’ll tell you what — I think they're telling me the truth. Because it was loaded on their iPods (when they had iPods back in the day). They do know the music. They know how to play it; they know the songs; they can sing it. So, they do like it, because they know all sorts of music. Their musical tastes are even more eclectic than mine.

TVO.org: What are some of the more contemporary artists that you like?

Steve: I can't confess to liking them as much as the folks that I loved back in the day. But when I hear my daughter, who's 17, playing stuff, I listen. Every now and then I'll say, “Oh, who's that? That's good.” You probably know these names better than I do. But you know, Post Malone and Eminem. Drake — okay, sure. Amy Winehouse to be sure. Lady Gaga — love her.

Lady Gaga performs “New York, New York” for the Sinatra 100 All-Star Grammy Concert in 2015.

There are a lot of great singers from this generation. They're just — I'm reminded of something Ken Dryden once said to me. I once asked him, “What was the greatest era ever for hockey?” And he said, “Whatever you were watching when you were 12 years old.” And that’s so true of everything. The music I was listening to when I was 12 and in my teenage years — none of that stuff is ever going to be bested by anything I hear today.

This interview has been condensed and edited for length and clarity.

Much more music show

Check out these other segments from Wednesday’s program.

Singer-songwriter Emm Gryner discusses her career in the Canadian music industry:

Heidi Van Vlyven, general manager of Toronto’s Jazz Bistro, talks about the unique challenges of running a jazz-music venue during a pandemic:




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