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Dan Callahan on His New Book, Bing and Billie and Frank and Ella and Judy and Barbra

In the last 12 years, Dan Callahan has written seven books, bringing to bear his capacious knowledge on cinema, acting, directing, cultural history, turning his detail-oriented gaze onto a variety of subjects. On writing about the art of acting, he has few peers. He started in 2011 with Barbara Stanwyck: A Miracle Woman, and followed it up with the first official biography of Vanessa Redgrave (I interviewed him about for it this site). He then wrote two excellent books on the history of American screen acting, spanning from 1912 to today. These are an essential survey course on the development of acting styles, and the important figures—from Katharine Hepburn to Al Pacino—who elevated the craft. Callahan helps you seek out the gems and guides you to watch and listen closely. His The Camera Lies was a fascinating analysis of actors’ performances in the films of Alfred Hitchcock. In 2018 came his first novel, That Was Something

His new book, Bing and Billie and Frank and Ella and Judy and Barbra, published by Chicago Review Press, is an ambitious collage, weaving together the journeys of six of the greatest singers of the 20th century. He examines what makes each singer distinct and explores how these singers and their extraordinary voices communicated to one another and to us. Reading this book is such a rich, rewarding experience. Every page sent me to YouTube, Spotify, or iTunes to pull up clips so I could hear what he described. Dan Callahan makes you pay close attention. I met up with Dan over Zoom to talk about Bing and Billie and Frank and Ella and Judy and Barbra

What surprised you in your research for this book?

Bing Crosby was the one I knew the least about, and I got very into him. In promoting these six singers on Facebook, a lot of people don’t like Bing at all. I’ve had comments like, “Bing stunk as a singer.” It’s an uphill battle.

Is it because he was a bad father?

Yes. I think people see his face and think, “Christmas. Bad Father.” But in the ‘30s and ‘40s, he was like the four Beatles rolled into one. He had nothing but #1 hits. Crosby was a steadying influence during the Depression and World War Two. He made a lot of movies. He was fine with doing slapstick. He’s fine basking in whoever he’s with: W.C. Fields, Ethel Merman, Louis Armstrong. He didn’t try to compete. If you start looking into Bing, it becomes very complex. I was bowled over by him, and I hope other people feel the same way. Did you become more interested in him from reading the book?

Yes. It was fun deconstructing my notions about him.

What were your notions?

Basically, he was the old guy standing next to David Bowie singing a Christmas song. As I was reading your book, I would listen to the songs you wrote about. They blew my mind.

He became Mr. Square later on. The early Bing is almost a Bad Boy. He had so much voice in the ‘30s. 

This book is about the human voice. The human voice is a fragile thing, and anyone who’s a singer knows that there comes a point when your voice doesn’t do what you want it to do anymore. Crosby was aware he had high notes, even falsetto notes, and he also had wonderful low notes. Over the course of 1939, you can hear the high notes are starting to go, and he knew it. In the ‘40s and then later, he doesn’t have any high notes left, but his baritone and bass notes always sound great up to the end, and they sound great in the way that no one else has ever sounded. Ella Fitzgerald was crazy about Crosby’s low notes.

You said Bing Crosby held something back.

He held a lot back.

He endured because of this?

Vocally, yes. He knew he needed to conserve his resources. I’m always discovering new things where I have to re-consider him. There are things about him I still don’t understand. Whereas Judy Garland, and Frank Sinatra, I feel like I understand them pretty well. We all know they’re great, but they’re Dickensian characters. Once you know who they are, they always behave in the way you expect them to behave. Ella Fitzgerald is like Bing in that she’s reserved. I love thinking about Ella.

What are your thoughts?

I wanted to get away from the cliches about Ella as an artist and as a woman. The cliche is: All she did was sing, and she sometimes was distant with lyrics because she was more about the music. Sure, but not all the time. She recorded an enormous amount between the mid-'50s and mid-'60s. It was her heyday. Ella recorded almost 40 albums in that ten-year period. There are some passionate, earthy, sexy recordings, too. What she’s doing is more complicated than what she’s given credit for. 

In high school English,
compare and contrast” was drilled into our heads. My understanding is that its not This is good and that is bad,” but “How is this like or different from that?” It assumes both have value. It seems writers now use compare/contrast like: This is good, and that is bad.” Your book is an example of proper compare/contrast.

That’s interesting. What you’re talking about was the most difficult thing in writing the book because I knew I needed to get it right. Nobody wants to read me trashing one version of a song over another. As you say, both versions have value. Sometimes one of the singers is wrong for a certain type of material, and I had to just say that, if that were the case. But I knew I needed to be careful.

Have you heard Bing sing Joni Mitchell’s “Both Sides Now”? When he sings “Don’t give yourself away,” it means something very different than when Joni sings it, but it’s just as touching. It’s not better or worse. Maybe that’s partly what we’re missing now, this give-and-take. It’d be very difficult to do a compare/contrast with contemporary singers.

You discuss what these people brought to the table as artists. So, for example, you have the self-pitying aspect of Sinatra –

It’s very attractive! Self-pity is usually unattractive. His self-pity is fabulous.

If you
re feeling that way, theres nobody better to listen to than Frank.

Billie is the same way. Ella does a version of “Good Morning Heartache,” which Billie Holiday was known for. Billie’s way of doing it is: “Let’s be self-pitying until we pass out.” Ella’s is: “I know about despair. But we are going to get through it.” Everybody asks me, “Billie or Ella?” There are certain singers for certain moods. There are also certain singers for different times of your life. When I was young, I would have said Billie. Now that I’m older, I say Ella. Billie and Ella are like Chaplin and Keaton. You don’t have to choose. Frank would appeal to me more than Bing when I was young. I’m very into Bing and Ella now, but I’m not young anymore. When I was young, I was listening to Billie’s nine Columbia CDs from 1933-1942. She laid down the groundwork for everything when she was young. Ella was the opposite. If Ella had stopped singing in the late ‘40s, she’d be known for that novelty song, “A-Tisket A-Tasket,” and that’d be about it. Ella was a late bloomer. When she did bloom, she wanted it all. She was like a librarian. She kept a book with note cards of songs, even if it was a jingle on the radio. 

A common thread in the book is the presence of Louis Armstrong.

He’s the thru-line, really. It begins with the friendship between Armstrong and Crosby. It was a tough thing. It was a different time. Bing took from Louis, Louis took from Bing. The “mordent” thing that Bing did, the fluctuation between notes, Louis sometimes does that. 

I loved the quote from Armstrong that Bings voice was like gold poured out of a cup.”

He also said Bing had a mellow quality nobody else had. If you listen to their recordings in the late ‘20s, early ‘30s, it’s almost like a conversation. But still. Louis said, “I’ve never been invited to a movie star’s house, not even Bing’s.” These social barriers were there. But like I say in the book, a conversation without barriers was going on in their music.

You capture how these singers were paying close attention to each other. Frank said singing with Ella made him nervous.

Frank was intimidated by Ella. In the ‘50s, they were both recording these long-playing records, and Frank wanted to be the best. Frank had vanquished Bing, but he’s listening to Ella do be-bop and scat singing, and he knew he couldn’t do that. Bing was thrilled by Ella, and Bing actually could do what she did at a modest level, and he was still doing it in the late ‘50s. And then Frank did an interview with Life magazine in 1965, and he takes aim at Ella for what he considered technical flaws. He takes aim at Judy too! Who had been his lover? This incident shows what type of man Frank was. Judy was in bad trouble at that point, and Ella was on the verge of exhaustion. He took aim at them when they were in vulnerable positions. 

Frank then records his September of My Years album, which, to me, is Frank at his most self-pitying and obnoxious. And Ella records Ella at Duke’s Place, which, if I had to choose just one of her albums out of her many great albums, it would be that one. So Frank criticizes Ella publicly, and she then records maybe her greatest album. She didn’t answer his criticisms in the press. She answered it with a great album. I’m being hard on Frank as a person. Listen. I’ve been listening to a lot of Frank again lately. His phrasing is out of this world.

If you had to pick a best album for each of them, what would they be?

For Frank, I would pick—and I believe Frank himself picked—Only the Lonely, because it’s the most emotionally exposed and Billie-like. What’s fascinating is he isn’t in the best voice on that album, but it doesn’t matter. He had a fragile voice, to begin with. When he opened his mouth, he didn’t know what would come out. For Judy, it has to be Judy at Carnegie Hall. For Bing, I would pick two of his singles from the ‘30s: “Out of Nowhere” and “Mexicali Rose.” With Ella, I’d pick Ella at Duke’s Place. With Billie, her greatest work is before the long-playing records. I’d pick the single “They Can’t Take That Away from Me” from the ‘30s. 

There’s also a live concert she did in Germany in 1954 where she sings “I Cover the Waterfront” with Carl Drinkard on piano, and it’s Billie at her best. When she sings a lyric like “the great unknown,” she’s in touch with the great unknown, and she makes you in touch with it, too. Frank was like that. When Frank’s at his best, he delivers a lyric and makes you understand what it means.

You call it method singing.”

Yes. Frank and Billie thought about their own lives when they sang, whereas Bing and Ella did not do that. Although, in the book, I say that sometimes Ella would do that. Like the Clap Hands, Here Comes Charlie album. She had a young Norwegian boyfriend at the time, and I’m listening to the album, going, “Oh, there’s something a little different here.” Ella was human; she wasn’t just a singing machine. She did an interview in the early '70s, and the host Brian Linehan says to her, “There’s a sexy quality about you,” and she looks delighted. If you listen to her music closely, it’s there.

You talk about how Billie Holiday deconstructed songs.

In the ‘30s, she would sing songs we think of as standards now, but they were new then, and she didn’t sing what was written. She was singing songs the way a jazz singer would in the ‘50s, 20 years later. When she would sing live, she didn’t care about pleasing the audience the way Ella did. Billie had negative thoughts about Ella as a singer that she wasn’t shy about expressing, not to the press but to other people. What I love, though, is that by the ‘50s, Billie changed her mind about Ella. She was listening with an open mind, and she heard that Ella had matured. She talked about it in interviews and praised her.

What about Judy?

Judy! On “The Judy Garland Show,” there’s some vocal damage here and there, but her voice is at its strongest. But in 1964, they pumped her stomach after a suicide attempt, and it damaged her vocal cords. They said, “Don’t sing for a year,” but you couldn’t tell Judy Garland what to do. She kept singing and never quite had the voice again because of it. Frank, somehow, kept his voice. He was still singing “Soliloquy” from Carousel when he was older, and he got away with it. He acted it. Frank and Barbra are similar. They both have enormous willpower.

s not forget about Barbra!

If I had to choose an album for Barbra, I would choose My Name Is Barbra and My Name Is Barbra, Two. Her voice is otherworldly on those albums. I also love The Broadway Album because my parents bought it when I was a kid and played it all the time. As a little kid, I thought, “What is this voice?” Especially her outer-space version of “Somewhere.” It really seems like her voice is from outer space. It doesn’t sound like any other voice. Her voice has this weird purity; it’s like a bell or a tuning fork.

A friend posted a clip of young Barbra singing, and what shes doing with her voice is wild, but there’s no strain on her face. Shes a vessel.

That’s the curious thing about her. There’s this ordinary person, and then there’s this extraordinary talent, and they co-exist. I say in the book: it’s like she’s Godzilla. There’s so much in her. There’s anger, rebellion. I love “When the Sun Comes Out.” The crazy high notes she does at the end is the most spectacular showing-off, and it stunned everyone. Louise Lasser said she went to see Barbra at the Bon Soir, and when Barbra opened her mouth to sing, Lasser started to cry, and she’s never been the same. Barbra wasn’t just a singer doing a song. She showed people something else. I had all these preconceptions about Barbra. I kept having to go back and re-write because I felt I wasn’t getting it.

What is it”?

Barbra is difficult to write about because she’s instinctively a negative person, but she wanted to be a positive person. It took an enormous act of will for her to be a positive person, even though she is a fatalist underneath.

When you write about her cover of Youve Got a Friend,” you say, If you call Barbra, shes not going to come running.”

It’s so true. She’s the Queen. The King of England isn’t going to come running if you have a problem. Give me a break! We wouldn’t want her to.

Yes! I dont need her for that! Of her early stuff, Lover Come Back to Me” is my favorite. Talk about deconstructing a song!

She sings that with Judy on “The Judy Garland Show.” There’s a wonderful moment where Barbra does a growl with her voice, and Judy laughs. She is so open to what Barbra is doing. At one point, Barbra’s hair is in her face, and Judy pushes it aside to help her. Judy was a competitive person—although not to Frank’s level—and yet Barbra was so extraordinary Judy takes it in. Barbra goes into their medley guarded, but when Judy moves her hair away, Barbra relaxes. When Judy hits the big note on “You and the Night and the Music,” Barbra throws her head back, like, “Wow!” Here are these two great singers, one on the way up, one on the way down, and they connect with each other.

When Judy sings, it
s life or death. Like OlMan River.” As you say, shes untouchable” there.

Judy sings about the injustices she sees around her. She feels things personally, but she knows it happens to other people, too.

There isn't a death wish in Barbra’s approach. 

Quite the opposite. She's the only one alive of the six in my book, and if anyone could figure out how not to die, it would be Barbra. There's just something about her that feels eternal. I wish she had never met Jon Peters. I wish she had people around her who would have pushed her to push herself. She wanted to play Medea. She wanted to play Juliet. But she stepped back. Let me make myself clear: I love Barbra. She’s done so many great things, but so much of it was early on. But so what? A lot of Billie’s greatest singing is early, too. Barbra’s got a memoir coming out in November, and it’s 1,000 pages long. I’m going to pore over it like the Dead Sea Scrolls. The thing about Barbra is, she chose life over art.

Who has taken up the torch from these six?

Rock ‘n roll and the singer-songwriter changed the game. Barbra is the last one who became a star singing Harold Arlen's songs. Show music used to be popular music. It would be like if Audra McDonald or Sutton Foster had a radio hit with a song from their latest Broadway show. This is why Barbra was slightly stranded. I’ve been a little harsh on Barbra, but you have to see how things changed so quickly. After her first ten years, there weren’t any songs—aside from Stephen Sondheim—for her to sing. What was she supposed to do? She was the last keeper of the flame, she’s the torch bearer. There are still fine singers doing stuff like that but not on her level of fame.

For me, Barbra’s legacy was set early with My Name is Barbra. The first ten years of her career? No one has ever started as strongly as Barbra did.

She was such a phenom.

Like I say in the book, nobody is listening to Barbra for restraint. People criticize her for being over-the-top or over-singing, but I don’t want Barbra to hold back. I don’t want Bing to wear his heart on his sleeve. I want them to be true to themselves. There’s greatness in both.

Bing and Billie and Frank and Ella and Judy and Barbra will be released on September 5, 2023. To order your copy, click here

Sheila O'Malley

Sheila O'Malley received a BFA in Theatre from the University of Rhode Island and a Master's in Acting from the Actors Studio MFA Program. Read her answers to our Movie Love Questionnaire here.

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