Sinatra Fans Climb Harbour Bridge

This story was covered on Episode 10 of SUDDENLY, The Sinatra Kids. All photos courtesy of the State Library of New South Wales unless otherwise noted.

Plenty of hacks have written about the 1940s bobby-soxer era of Frank Sinatra fans. The story always hits the same few beats: riots, screaming, the egg-throwing, the supposed wet seats. The setting is always New York. It’s become a rock’n’roll cliché.

Others have written plenty about Sinatra’s impact on Australia. The 1974 incident gets trotted out again and again. There’s usually an afterthought about the 1988 concert at Sanctuary Cove, Queensland. If you’re really lucky, you might even get to hear about the legendary 1959 Melbourne concert with the Red Norvo Quintet.

But there’s a part of the story that everyone missed.

On January 19th, 1945, Sinatra’s film Step Lively opens at Sydney’s Empire Theatre. (It’s long demolished now, but it used to be right near Central Station and adjacent to triangular bus terminal Railway Square.)

The Empire Theatre under construction, 1927.

Inside the Empire Theatre, circa 1930s.

That night, 30 teenage Sinatra fans get off the train at Central and walk excitedly down to the theatre. It’s easy to imagine how excited they must have been. It’s worth remembering that at this time there’s absolutely nothing like the internet at all. You’re a teenager with a favourite singer and this is basically your only chance to see what he actually looks like, singing, moving and walking around. It’s also wartime, and it’s been wartime for six years. People are bored, frustrated and fed up - especially teenagers. They need diversion and entertainment, and friends. They need a club to belong to.

When they arrive at the Empire, they are met by a waiting angry mob of 300 adults who are there specifically to assault and harass them.

A young woman, Shirley Ryan, has her arm twisted behind her back. Kicks and punches fly. The mob jeers and boos these kids. Bruises form. The word “swooners” is heard, spat out in the manner of a derogatory slur.

Imagine being 14 or 15, going to something like this, and being met by 300 adults who are there to hurt you. Outnumbered ten to one.

Police arrive and break it up. But the angry mob have also themselves bought tickets to the film, so the incident carries on inside. When Sinatra appears on screen, a noxious mixture of screaming, crying and loud, aggressive boos fill the room. His presence on screen is an emotionally loaded thing for everyone. You could almost miss that it’s a boring and not very good movie.

After the film ends, the angry mob stalk the young fans through the streets on their way home.

What the hell was all this about?

To understand what happened, we first need to remember that there was a time when it was very much uncool to like Frank Sinatra. Today, he is very much considered “real music.” He is a “man’s man”, a “they don’t make ‘em like they used to.” He’s a bastion of authenticity, widely considered one of the most definitive voices of the 20th century.

But here’s what mainstream Australia thought about Frank Sinatra in 1944, as reflected in an editorial in Melbourne’s Advocate:

I have yet to meet an Australian who can appreciate the nuances of Mr. Sinatra’s art.” (This is meant to be sarcastic.) “He must be regarded, like flood, fire and famine, as a temporary disaster from which the world with its wonderful recuperative powers will soon recover… The fact that Sinatra has managed to strike deep into the heart of a certain type of American co-ed is taken as sufficient justification for circulating his monotonous and unpleasant recordings… He will not last, of course. I would be willing to tip that in twelve months he will be a thing of the past and some other foghorn, wheezer or vocal ghoul will be dribbling his undigested art into a microphone.

Weak, feminine - Sinatra. Not real music - Sinatra. Can’t sing, won’t last - Sinatra. It is now difficult to even understand.

To be fair, this was long before Capitol Records, Nelson Riddle and most of the timeless Sinatra hits most people listen to today. The early 1940s was the era of his Tommy Dorsey “crooner”-style recordings. Don’t get me wrong; Sinatra of this period is still a great artist in fine voice, and Dorsey’s arrangements were masterful. It’s just safe to say that this era is not the one people most associate with Sinatra today.

Still, the fact a “he can’t sing” level anti-Sinatra mentality was once common thought now feels pretty surreal. It has been all but memory holed in the Australia of today.

Next, we need to know about Alexander Dorogokupetz, the boy who threw eggs at Sinatra in New York.

Alexander Dorogokupetz, photo from New York Daily Times.

Dorogokupetz has been written about extensively elsewhere. In 2019, J.P. Robinson wrote a fantastic article about him, The Egging of Frank Sinatra. Seventy-five years after the original egging, Robinson definitively sets the record straight about who Dorogokupetz was and where he ended up. It is highly recommended reading.

For our purposes it is sufficient to note that in 1944, Dorogokupetz became briefly world-famous at age 18 after throwing eggs at Frank Sinatra at a concert in New York. In Australia he was even considered a national hero, though the media here misspelt his surname “Dorogokleepetz.”

The Melbourne Advocate editorial went on:

This kind of thing (Sinatra and his fandom) has gone on for too long now, and I feel, along with many others, that something must be done to stop it… Will anyone come with me on a record-smashing expedition? What about unfurling the flag of the Dorogokleepetz Society?

Similar articles appeared around the country. In The Argus:

Only a few weeks ago, I saw and heard Frank Sinatra on the screen at the Capitol. While he was making his noises … (my thoughts ran) on the pleasures of heaving something heavy at the source of the outrage. But my mind has always toyed with ideas of half bricks or road metal. I think that Mr. Dorogokleepetz has the more practical and constructive mind. I envy him his courage. I would never be game enough to translate these thoughts into deeds.

Two weeks later, follow-up articles appear. Apparently people have written in, earnestly supporting this “Society.” A farmer has offered to supply eggs.

Dorogokupetz is even referred to as “our beloved Führer.

Third, we need to understand the “bobby-soxer” phenomenon. This is another topic that has been widely written about elsewhere.

Essentially, bobby-soxers were teenagers. Teenagers who liked teenage music and did teenage things. They weren’t frivolous people, but they were enthusiastic about their interests and knew how to be fun and silly.

They really, truly loved music. Their signature garment was white socks, pulled up high. They liked their favourite singers and hung out with their friends.

Once again, they were basically just human beings in their teen years, going through normal developmental stages. And a lot of them were really into Frank Sinatra.

This all seems like nothing now, but it was a relatively new social concept in the 1940s.

In the US, an entire episode of the famous newsreel series The March of Time was devoted to the topic of “Teen-Age Girls.” This is a surreal watch now. Though it is of American origin, it makes for helpful context to the Australian story we are now in the middle of. This is a time in which the fact teenage girls exist is literally considered breaking news.

If this all seems familiar to us, it should perhaps also come as no surprise that bobby-soxers were the target of much scorn from wider society in the mid 1940s, both in Australia and the US. We can pin that one down to just your garden-variety misogyny. Young women like something, so hey, guess what - it’s considered a stupid thing to like. We’ve seen this mentality many times in the decades since, and we’re nowhere near done with it.

One thing that people really hated bobby-soxers for was “swooning” over Sinatra. The concept of swooning comes up a lot in the rest of our story. Basically, the haters saw the enthusiasm for Frank as pathetic, weak behaviour. Deep down, I have no doubt they were jealous of the attention.

People don’t think of Sinatra as gender-ambiguous anymore. Sensitive, yes, but not effeminate. But in early 1940s Australia, there’s only one word for how he was considered: queer. He was something closer to the David Bowie or Prince of his time than we now realise.

So, when Step Lively opens at the Empire Theatre in Sydney on January 19th, 1945, these are the three incendiary factors at work:

* the general public’s hatred of Sinatra, largely because he is perceived as feminine;
* the misogynistic backlash against “swooning” “bobby-soxers”, and;
* weeks of anti-Sinatra incitement in the Australian media, largely as a result of the Dorogokupetz egging.

And this is why 300 adults turn up to a theatre to assault and bully 30 teenagers, just for going to see a movie with their favourite singer in it. It’s frankly embarrassing behaviour, far more juvenile than anything a child could ever do.

The hot takes that follow are painful to read. One comments that the riots should have been “followed up at home with a little old-fashioned slipper work”, i.e. beating your wives and kids. Another openly articulates the unspoken incel sentiment behind it all: “Women and girls who pretend to faint when they hear Sinatra should undergo medical treatment… They would not go out of their way to give a cheer to men who have earned the decoration for bravery, yet they would willingly surrender their bodies to a hideous wailer.

And here’s what Joy Wilson of Mosman has to say, writing in to Sydney’s Daily Telegraph:

The mob behaved in a similar way to a mother who, shocked and baffled at bad behaviour in her child, turns on it and punishes it for actions for which she herself, in her ignorance, may be responsible… This report of misdirected adolescence (of the Sinatra fans, she means) must be regarded as a cry for help! What perfect victims these children would be for a fine uniform and the drug of Fascist emotionalism!”

Joy thinks that the Sinatra fans going to a movie for fun with their friends are the potential fascist recruits, not the violent gang of adults who beat up on teenagers and call Dorogokupetz “Führer.” She goes on:

Something must be done, and done at once. We must have a good children’s library in every suburb. We must have permanent, all-the-year-round play centres… that every child can pursue whatever creative interest they may choose.

Oh, Joy. You’re so, so close to getting it.

In February 1945, with the Step Lively riots still making national news, the Sydney/Melbourne rivalry is projected onto the classic Bing Crosby/Frank Sinatra rivalry.

And so, apparently, someone in Melbourne starts an “Anti-Sinatra Club”, or “Bing Crosby Club”, out of a RAAF base. Basically just to spite these teenagers in Sydney.

They claim their logo is a scarlett raspberry, and their motto is “In Fealty to Dorogokleepetz.” It’s not clear how much of this is a joke, or how much actually went ahead.

It’s interesting, actually: in all the articles about this new Anti-Sinatra Club, they can’t seem to make up their mind about whether they’re against crooning in general or specifically for Crosby and just against Sinatra. The two positions seem to be interchangeable. Crosby, it seems, is the “man’s man” variety of crooner - Sinatra is not. This too is difficult to wrap one’s head around today. One of the members is quoted as saying:

"We don't want this club debased into a crooning fan organisation. It is meant to be an intelligent process against the pandemic of erotic hysteria, which has followed the hypothesis of Sinatra."

Reading between the lines, let’s be real: being “anti-Sinatra” really means hating young women.

Astonishingly, the Anti-Sinatra or Bing Crosby Club later had their own riot. In May 1945, a Crosby-themed dance is organised at the Melbourne Town Hall. Three thousand tickets are sold, and just as many people on top of that show up demanding to be let in. When barred from entrance, they try to smash windows and kick in doors. Only police involvement puts a stop to it. Whenever Sinatra’s name is mentioned, the crowd boo so loudly that the marble walls rattle. This evening becomes the second Sinatra-related incident of mass public disorder in Australia in less than six months.

Inside, it’s so crowded that there’s no room to dance.

Later in 1945, Australian journalist Colin Simpson interviews Sinatra while in New York. The article runs in Sydney’s The Sun as “Sinatra: A Decent Bloke.” This is a remarkable interview that is really worth reading in full. I have never seen it referenced or quoted elsewhere. Simpson seems to have caught Sinatra giving no fucks, defending his fans and sounding as politically radical as perhaps ever in his career.

It is noteworthy that in the middle of all of the post-Step Lively riot ruckus, Sinatra was quoted in the Australian media as saying the following:

The prejudice in this country that calls itself a big Democracy - it stinks! It’s just lousy! It’s worse than when I went to school!… If I had my way, I’d wipe out negro segregation like they have in the South, right away. If it’s wrong for me to speak out about what I think is right, then to hell with my career!

Kids are not born with any racial or colour prejudice. Someone has got to put the prejudice into their heads. A lot of parents do it… Bigotry is as much part of American history as Puritanism. I am ashamed there is so much of it in our democracy. It’s a bad situation, and corrupt politics and slanderous mobs are part of it… I guess I like people and I hate to see them denied their rights and kicked around.


Listen, I was just a kid from 115 Monroe St, Hoboken. It’s very much the wrong side of the tracks. You know where a lot of the other kids from that street are now? They’re in gaol. I got a break. Those other kids didn’t get breaks. I don’t see why!… I never knew any kinds who wouldn’t have turned out all right if they’d got the right steering and a break… Get right down to it, there aren’t any juvenile delinquents. There are only parental delinquents.

(The fans don’t swoon.) That’s a lot of bunk. They act up, they scream, but they don’t swoon. They yell for the same reason that when I take a night off I go to the fight at Madison Square Garden and sit up there and yell my fool head off. I like to have a yell and so do they!… I don’t see any harm in it.

It’s music, isn’t it? What’s wrong with kids yelling about music?"

So what becomes of the Sinatra Club? What’s it like being caught in the middle of a national scandal, just for going to a movie with your friends?

This is where the story gets really lovely.

In March 1945, two months after the Step Lively incident, an article defending the young fans runs in PIX magazine. PIX was a photography-based news magazine based out of Sydney that wasn’t afraid to run offbeat stories and showcase alternative perspectives on life. Much of their success came from the work of one particular photographer, Ivan Ives.

The intention of this article is to show through Ives’ photography that the kids in the Sinatra Club are not “swooners”; that they are, in fact, thoughtful young people with a passionate interest in music, socialising and bonding over their common interest.

A range of photos run in this article. Here, we see the club returning to the Empire Theatre for another screening of Step Lively. Notice that they are shown to be calm, interested and intellectually engaged - not hysterically weeping, as the conservative media kept insisting.

In these shots, we see them just hanging out in the wild. They’ve brought their portable gramophone out with them, and Sinatra’s records accompany them on all their adventures - even while swimming. It’s as if a holographic Sinatra is standing right there with them. The voice, the photos say, is what bonds them together.

Most remarkable are a series of candid portraits that capture the young fans’ emotional responses as Frank Sinatra records play in the background.

We don’t see weeping, swooning, or hysteria. We just see young people, lost in great music that they love.

And here, the two-page article ends.

While brief, this is a remarkable piece of photojournalism that deserves to be remembered for its courage, empathy and kindness.

But only a small number of the photos that Ives took of the Sinatra Club actually ended up in the article.

The full photo set sat in a archive somewhere, unpublished, for over 70 years. Eventually, that archive was donated to the State Library of New South Wales. Then, at some point in the 2010s, a volunteer scanned and digitised them all and uploaded them to the Library’s website.

And so I am thrilled to share these precious, beautiful photos with you:

You can view the entire set of 31 photos at the SLNSW website here. I’ve also backed them up myself, along with other clippings from relevant news articles of the period, to Internet Archive.

To me, Ivan Ives emerges as the hero of this story. There is one remarkable photo from this set in which a third party has taken a photo of Ives at work, directing the club and setting up the shot of them listening to the gramophone around a bench in Wynyard Park. You can almost hear his voice saying something like, “Just act natural. Listen to the music.”

This photo probably would never have made it into the article, which raises the question: who was it for?

I can only think of one answer: Us.

Meanwhile, in Melbourne, a very different kind of Sinatra fan club is formed.

Years before Sinatra’s Mafia associations are common knowledge, the St. Kilda Sinatra Swooning Slaves Society are running in the streets and not to be fucked with.

Their leader is Oliver Gilpin Jr., a rich kid behaving badly, son of the chain store proprietor of note. At one stage, police arrest four of the “Slaves” after finding them standing over a man lying on the ground with a bleeding face, late at night in Alma Park. Batons are found in the Slaves’ possession. They later tell the court they need to carry them, as they’re in the middle of a rivalry with another crew from South Melbourne.

And they become infamous for their parties. One night in 1947, a rager is thrown for Gilpin’s 18th birthday at his mother’s house in Inkerman Street. The story of what happened that night was later reported in great detail in The Truth.

This in itself requires some context. In Russia, where the official state newspaper is named Pravda (Russian for “Truth”), they have a saying: “Pravda ne pravda.” In English, this translates as “The Truth is not the truth” - a phrase that would have worked just as well in 1940s Australia. Anything written in The Truth was understood as having been written with dramatic flair, and needing to be taken with a grain of salt.

Even allowing for this, what seems to have happened is that the Sinatra Slaves fucking trashed this guy’s mum’s house:

The house, ablaze with fairy lights, was wired for sound so that the noises made by Mr. Sinatra could be heard by not only the neighbours but by most of the suburb as well. The hepcats hepped and the chicks cheeped. Rugs were cut and everybody got in the groove. (Then,) a red-headed woman was the cause of it all… This red-head put down her glass and said, for all to hear, ‘Sinatra stinks.’

In the near melee that followed, ornamental garden plots, garden seats and tree branches were tossed into neighbouring yards. About 100 crystal glasses and bottles were smashed with youthful abandon on the back lawn. Intoxicated youths rushed girls who were lined up giving away kisses, and some who were not… 20 guests had to be given a shower, clothes and all. Eight taxis had to be called to get rid of the fans after they nearly overturned Mrs Gilpin’s crystal cabinet.

The party was officially over at 2:30am, but when the morning dawned, six slaves were found lying on the glass-strewn lawn.
Oliver says he doesn’t mind what happened.

And it gets wilder from there. Apparently, after this story ran in The Truth, the gang went back to the house and home invaded Mrs. Gilpin, demanding that she correct the record. They stormed the Truth office too, who wouldn’t pull the story. They then went back to this lady’s house, and she had to barricade the door to stop the Sinatra Slaves from getting in. Again, who knows how much of this is true, but what a yarn.

Yet for all this, apparently the Slaves deep down had their hearts in common with the wholesome Sydney club after all. They apparently host “listening parties” in which they sit in silence and enjoy Sinatra’s music:

The 'out-of-this-world' singing is allowed to cloud the listener's mind in much the same way as opium. As the record plays there is rapt silence among the young audience. Teen-agers rest their heads against chairs, close their eyes — and just listen.

That’s what it always comes back to: The voice. That damned voice.

This is either a photo of the St. Kilda Swooning Sinatra Slaves, or another Sinatra fan club from Melbourne at this time - I am not sure.

There’s so much more I want to know about all of this, plus some details that made the podcast episode and didn’t make it here, and vice versa. But there’s one more detail I’m going to share with you, because I think it wraps up this whole thing perfectly. In August 1947, this story pops up in Sydney:

I don’t entirely know what to make of this.

Some context for people who don’t live in Australia: These days, every tourist climbs the Sydney Harbour Bridge. You’ve probably seen photos of various celebrities climbing it. Anyone can do it now through a company called BridgeClimb. But that only started in 1998. If you “climbed the Harbour Bridge” in 1947, that really means you climbed it. You manually climbed up without help. That means Spiderman sort of shit. An incredible achievement. Some people used to do this back in the day. It’s not unheard of among a certain generation. But it would be absolutely impossible now.

I did find one other article on this in which one of the two Sinatra climbers is quoted. “We did it just for the hell of it”, he says. “We like the risks but don’t fancy any court appearances. We have explored every railway tunnel in Sydney and climbed every railway tower.”

Is it serious? Part of me thinks that maybe these are completely unrelated people who mentioned Sinatra’s name as a joke. But no, I want to think that this is legitimate. I think there is just as much chance that it is. I want to think that out of the original Sydney fan club, two of them started an urbex offshoot the went on to climb and explore the city.

I’m imagining two of the guys in the above photo getting to the top of the Harbour Bridge just after midnight, and taking in the view of Sydney.

I want to close the curtain here, because I love this as an ending so much. I really, really want it to be true. So let’s say that it is.

There is much more to this story and possibly more will come to light in the future. It was explored in detail on Episode 10 of SUDDENLY, The Sinatra Kids.

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