In the spirit of Father’s Day, we’ve unearthed four examples of children dearly disappointing daddy dearest.



Fatherhood. As far as I’ve experienced it, it is a series of moments underpinned by rewarding doubt, mistakes made and clutch decisions made under duress which have lasting effects on your progeny’s psyche. It’s a tough gig. However, beyond the surface challenges, I feel that what you want most for your kids is that they surpass you, learn from your mistakes and make their own.

Saying that, if the trail blazed by the father was up a mountain too far for the next generation to ride, what happens then? What of those who seek to emulate their father’s example, but alas, fall short? Well, in the spirit of the day, let’s have a quick silent peruse at those who didn’t make it out of Daddy’s long shadow.


Vincenzo Galilei

Who? Son of the transformative Astronomer and round-earth truther, Galileo Galilei.

Vincenzo did as many sons before and after did and will do; he disappointed his father by becoming a hipster/artist. Dropping out of law school to play the lute, Vinnie spent most of his time (and fortune) investing in musical instruments, doing acoustic covers of Baroque classics, jousting maidens of ill repute and arguing with Pa.


You're learning to play the...what?

You’re learning to play the what?


Frank Sinatra Jr

Who? Trifle obvious, but the son of the king of croon (and 1950’s exceptionalism) Frank Sinatra.

Poor Frankie Junior. In a tale older than the Galilei’s, he decided to climb the wall of ignorance erected by his father by becoming just like him. It started well, but after being kidnapped in 1963, he was soon released to murmurings that it may-or-may-not have been a career stunt orchestrated by the old man (figure that one out). His career stalled by virtue of looking and sounding a lot like his father, but not being his father.

A tragic combination of timing, a passing of a generation, and the passing of his father, Junior said in 2004 that his “(lack of) success does not trouble me at this stage in my life,” before summing up his life in the grating sentence: “I was trying to sell antiques in a modern appliance store.”

Frank Sinatra Jr passed away in 2016.




William Burroughs Jr

Who? Son of the original beat poet and heroin addict extraordinaire, William S Burroughs.

Oh, Billy Boy. The Burroughs could be seen as the parallel of the Sinatras. A towering brilliant talent, and a son desperately seeking his father’s attention. However, if the Sinatra family gene is swing music and tuxedos, the Burroughs family affliction is drugs, and taking it much too far. To put it simply, Father was not a very nice man. Brilliant, but a bit of a massive you-know-what

Anyway, young Billy’s life was a trifle rough. The Burroughses momentarily relocated to Mexico, where much merriment was had. William Sr fighting his own sexuality and his own demons (drugs, booze) decided to spice up the family vacay by killing their mother while trying to shoot a drinking glass off her head à la William Tell.

What followed was Father’s success as a writer with Junky, Queer and Naked Lunch, which discussed compressed sexuality with a heavy sprinkling of drug abuse. William Sr quickly became an icon and the king of literary heroin. Or, heroin in general.

Now, Billy, desperately seeking his Father’s attention wrote Speed, a novella about his encounters with the drug speed, before the book flopped (seen as a pale imitation of Pa), and then decided if he was not going to out-write his dad, he’d get as hedonistic as him, diving into the bottom of many a bottle.

Incidentally, Billy Burroughs was the first man in America to receive a liver transplant but died in 1981 at the age of 33. Which is a pale shame, because his prose is beautifully bent.

“Had it been sublime to be born in time, hospital halls unknown, mother soon to be blown from the face of the earth, a bullet hole in her head, father pale, hand shaking as he lit the wad of cotton in the back of a little toy boat in a Mexico City fountain. The boat made crazy circles as the poplar trees trembled, and our separate fates lay sundered, he to opium and fame, bearing guilt and shame. And I, the shattered son of Naked Lunch, to golden beaches and promises of success.”



Santino Corleone

Who? Impetuous son of Vito Corleone, the Don of the Corleone crime family.

Yes, he doesn’t exist. But there’s truth in the fiction. The next in line to the throne, Santino embodies everything that his father does not. He eschews logic for rash, impulsive thought, he chooses to forgo good family values by remaining unfaithful to his wife, and chooses violence over the business. Add up all of that, and this happens:



Anyway, the reason why I brought the sordid tale of butchered youth, is to close on a statement uttered to subtextually undermine Santino, passed by the (God) Father of us all, Vito Corleone.

Don Corleone: Tell me, do you spend time with your family?

Johnny Fontane: Sure I do.

Don Corleone: Good. Because a man who doesn’t spend time with his family can never be a real man.

Antiquated bravado perhaps, but to all those fathers out there, and especially to those who have the responsibilities, but not the title, have a wonderful Father’s Day spent with your family, whatever that may be.






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