Sixty years ago this fall, the 33-year-old Gay Talese flew from New York to Los Angeles to report a cover story for Esquire, the “It” magazine of the 1960s. His quarry was Frank Sinatra, the reigning entertainment icon of the 20th century, then on the verge of turning the irksome age of 50. To complicate matters, Talese didn’t feel like writing about Sinatra, preferring non-celebrity subjects, while Sinatra, hampered by post-nasal drip, didn’t feel like talking to Talese. (“Which turned out to be a good thing,” Talese says.)
The resulting game of cat and mouse produced what is arguably the greatest magazine profile in the annals of journalism, “Frank Sinatra Has a Cold,” which ran in Esquire’s April 1966 issue.
The cover featured an illustration of the singer done in a style of pure electricity by a 36-year-old artist named Edward Sorel. Talese and Sorel—both making their Esquire-cover debuts—would soon become titans in their respective fields. They are now 93 and 96, respectively, and have had occasional brief encounters with each other since the Sinatra story ran. But they had never enjoyed an extended hang until Air Mail brought them together not long ago at Talese’s Upper East Side town house for an afternoon of recollections, jokes, and insights into the man they captured, one with a portable Olivetti and the other with a Speedball B6 pen point.
MARK ROZZO: Ed, tell us how you caught this assignment from Esquire.
EDWARD SOREL: There’s a story, actually. I had already left Push Pin [the legendary design-illustration studio founded by Sorel, Milton Glaser, and Seymour Chwast], where I was taking $65 a week. When I left, I went over to CBS and got $175. I was very happy, but I didn’t know what I was doing. So, to avoid getting fired, I then left CBS. That’s when George Lois [Esquire’s freelance art director and cover-design whiz] asked me to do this cover. Push Pin was still very hot, because Milton and Seymour were very good and Esquire was using all that stuff. George assumed that I had something to do with it, but I was a weak link at Push Pin. So I got very nervous.
M.R.: And Lois already had a cover idea in mind.
E.S.: Yes—a lot of people wanting to light Frank Sinatra’s cigarette. So I did a rendering of George Lois’s idea.
GAY TALESE: Harold Hayes, the editor of Esquire, had an idea for a photographer doing it. But then Hayes got pissed off at Sinatra’s publicity guy, Jim Mahoney. For spite, Hayes got this guy [Sorel]!
M.R.: So Hayes, being angry at Sinatra for not participating in the story, goes straight to the numero uno caricaturist, who’s known for skewering his subjects.
G.T.: Hayes was so fucking pissed off at Sinatra. So this guy took care of it!
E.S.: But I wasn’t numero uno. I was hanging on by my fingertips! I wasn’t getting any jobs, but George thought I was good. He was a minority. So I did this overworked—Jesus Christ, when I get scared, I overwork everything. So I gave him this lousy drawing, and he rolled his eyes and said, “I’ll give you 24 hours to re-do it.” I had to deliver it the next day. There wasn’t time to do any tracing. But when I trace, it dies; when I work free, it lives. So I just did it, worked through the night. In the morning, I went to George, who had his own agency, and showed it to him.
M.R.: Was he happy?
E.S.: He was happy.
G.T.: Ed, do you remember what they paid you for that?
E.S.: I doubt whether it was much more than $500.
G.T.: And they own it, don’t they?
E.S.: No. I had to fight to get it back.
G.T.: You and Taylor Swift!
E.S.: Now it’s in the National Portrait Gallery. They paid me $15,000 for it.
G.T.: Wow. Really?
E.S.: Yeah.
G.T.: Trump is going to change that, you know.
E.S.: Too late. I got my $15,000!
G.T.: Ed not only did the cover, he did the inside drawings, too. Not that he ever read the article, I don’t think.
E.S.: Who, me?
G.T.: Not you. Sinatra. I don’t think Sinatra ever read my article. He couldn’t get past the cover! Sinatra hated Hayes for that. And it got off onto me. I wrote a good piece, but this cover made him look like a rat.
M.R.: Ed, when you’re looking at Sinatra, what are you trying to draw out of him to create an image?
E.S.: I just wanted to exaggerate the features. I mean the ears. He’s got big ears. He must have had a mastoid operation. When I was 16 years old and on summer break from high school, I was working at the Adelphi Theatre selling “ice-cold, fresh-fruit lemonade” up and down the aisles. On the Town was playing. Sinatra came in one night. He had these scars, so you could see that he’d had a mastoid operation. [The singer did, in fact, have a childhood operation to remove diseased cells from the mastoid bone behind his left ear, a procedure that left him with permanently damaged hearing.] And he was very short.
M.R.: He was five-seven, but he put something in his shoes to lift him up. Gay reported that.
G.T. (inspecting Sorel’s illustration): It looks like him.
M.R.: It does. Was this a breakthrough for you as an artist, Ed?
E.S.: Yeah. Before this, my sketches were always better than my finishes. And so it was a question of getting into my finished art some of the energy that the sketches had.
M.R.: So Hayes obviously loved the cover.
G.T.: Yeah. And Hayes, he was a very good editor.
M.R.: He was your hands-on editor for the piece, wasn’t he?
G.T.: Yes, and I wrote about 30 pieces for him. Easily.
M.R.: Gay, going back to Hayes’s initial idea, were you at all disappointed that Esquire didn’t get a fabulous photograph for the cover?
G.T.: Well, the piece without the illustration had a tone about it that was … mellow. It was a very under-written piece. My writing is basically under-writing. Tom Wolfe was a flashy, pyrotechnical writer. I’m almost the opposite. But this, being illustrated by Ed, gave such a smack to the Sinatra profile. Like I said, he’s a rodent surrounded by sycophants with cigarette lighters. Usually photographers—whether they’re Art Kane or Annie Leibovitz—are somewhat flattering to their subjects. This was not flattering at all, and that tone slipped into the whole article.
M.R.: What was the initial reaction to the piece?
G.T.: That piece, when it first came out, did not have a lot of attention. Later on, 10 years, 20 years, 30, when it started to be reproduced in anthologies and taught on college campuses—that’s when it caught. When it first came out, there was no sensation about it at all.
M.R.: I’ve been teaching “Frank Sinatra Has a Cold” in nonfiction-writing classes at Columbia since 2009, and it only seems to grow in renown year after year. You must be pleased about that.
G.T.: Well, it was not my assignment. I was told to do that piece. When I left The New York Times, in 1965, after 10 years, I was so enamored of my colleagues on the paper, like the managing editor, Clifton Daniel, and the obituary writer, Alden Whitman, that I thought they were stories. I wanted to write those stories, and Hayes said I could. So I signed a one-year contract in 1965 to do five, six pieces. But they said, “You’ve got to do Sinatra.” I tried not to: “No, he’s overdone!” “You have to do it! Cover story.”
M.R.: What were you reading at that time, in 1965?
G.T.: I was reading Irwin Shaw, John O’Hara, Carson McCullers, Mary McCarthy, F. Scott Fitzgerald, John Fowles. A lot of fiction. I wanted to do in nonfiction what fiction writers did in their own work without changing the names of the characters. I wanted to break through as a nonfiction writer into the more elevated life of the fiction writer. I wanted to crack that ceiling—without succumbing to fiction.
M.R.: When Hayes asked you to profile Sinatra, were you thinking it would be a challenge to elevate that story to the level of fiction because the subject was such a celebrity?
G.T.: No, I just didn’t want to do celebrity pieces. I was forced to do Sinatra as a trade-off that would allow me to write about those subjects I wanted to write about, because no one wanted to give a writer 10,000 words to write about a New York Times journalist. You’re not going to sell copies that way. And none of those things were cover stories. But Sinatra was a cover. And I hadn’t had a cover story.
M.R.: In other words, that cover exposure was as important for you as it was for Ed.
G.T.: But a reason I didn’t want to do it was that I sort of liked Sinatra. I grew up with Sinatra. I was from Ocean City, New Jersey; I knew Sinatra had been to Atlantic City. I was Italian-American. My father was an immigrant from Italy, from Calabria; Sinatra’s father was an immigrant from Sicily, right across the Ionian Sea. I don’t want to write about people that I feel close to. And even though I never met him, I felt close to him.
M.R.: It seems almost like Hayes was profiling you with this assignment: Let’s get the Italian kid to write about the Italian superstar.
G.T.: As an Italian-American born in 1932, I’m 10 years old in 1942, and my uncles are both in the Italian Army, fighting Americans. I felt very misplaced, fractured. I felt somewhat half American. My father was a patriotic American citizen, but he also had this emotional connection to his homeland, to his mother and his brothers. Sinatra bridged the gap. He was a person of Italian origin who could be assimilated into the American mainstream. Sinatra did that first. Joe DiMaggio didn’t do that. He was never a public person, even when he married Marilyn Monroe. He was a self-centered guy. Sinatra was not self-centered. He was all over the place. He was outgoing, a great example of an Italian-American who could be liked by all Americans, including the kids I went to high school with and the mothers in my mother’s dress shop, who were not Italian. Ocean City was a WASP-y town. So when I got out to L.A. to do this story and got the brush-off from Sinatra, I was a little bit upset.
M.R.: Yet he let you stay right there on his periphery for weeks, even while refusing to talk to you. Do you think being Italian-American had any bearing? Like, Sinatra thought you were “good people”?
G.T.: You would think it would be an advantage, but it wasn’t. He had a lot of Italians around him, like Jilly Rizzo.
M.R.: Right. And Jilly drove you to Fort Lee so you could interview Sinatra’s parents after you got back from L.A.
G.T.: Yes. I had written a piece on Jilly, so he was in my corner. I said, “Jilly, help me out! I can’t get anywhere with Frank. I’ve got to do this piece. Can you get me to see the parents?” He wants to clear it with Frank, obviously. But the parents agreed to see me. So Jilly drove me out there and later got me to see Sinatra’s son, Frank junior. I think Sinatra reached a point where he realized I’m not going anywhere. And I think he respected that. As long as I didn’t bother him, he wouldn’t bother me. But I would never, without his permission, have been able to see his parents.
M.R.: So you report in November and then come home and write the piece in December, or is it after the holidays?
G.T.: It was January. Or around Christmastime. It took me at least two months.
M.R.: I’ve been playing a mental parlor game for decades, which is imagining “Frank Sinatra Has a Cold” at The New Yorker, with William Shawn, instead of at Esquire, with Harold Hayes—what might have happened in terms of editing, structure, tone. Maybe this is another way of reiterating how singular Esquire was in its editing and in the stories it ran.
G.T.: I don’t think Mr. Shawn would have bought that piece. I never did deal with Mr. Shawn. I just thought, “That’s too beyond me.” Even though his magazine was not that good. When I was a kid, I would have liked to have been at The New Yorker, but Shawn would not have a guy like me around, I wouldn’t think. Now I wish I was younger, because if I was younger I would be writing a lot for The New Yorker.
M.R.: Ed, you did so many classic illustrations for Esquire after Sinatra—people like de Gaulle, Nixon, even the Maharishi.
E.S.: Yeah. They weren’t very good.
M.R.: You don’t think so?
E.S.: I was still learning. They were very tight, with big heads. They didn’t have much life. They looked like 19th-century caricature.
M.R.: Were you inspired by that kind of caricature?
E.S.: No. I was just scared and insecure.
G.T.: But Esquire … Harold Hayes was a great editor. Courageous. He let you do what you wanted. The Times was heavy editing; Esquire was not heavy editing. Space. Time. Three months to do a magazine piece! I flew out there and spent six weeks in a hotel. And they had good writers. Tom Wolfe, Norman Mailer.
M.R.: James Baldwin.
G.T.: I loved him. He was terrific.
M.R.: Gay, do you think that piece could have come together anywhere else, at any other time?
G.T.: “Sinatra” would have been turned down in later years by everybody. I don’t think I’d have had the space—15,000 words! Or the expense account.
Mark Rozzo is an Editor at Large at AIR MAIL and the author of Everybody Thought We Were Crazy: Dennis Hopper, Brooke Hayward, and 1960s Los Angeles
