Appreciating the Dark Cautionary Tale of Sondheim’s Assassins


When looking back at the endless musicals made about the good old U.S. of A, there’s a handful of big ones that we think about. The two most prominent ones in recent years are 1776 and Hamilton, which both have this reverence for how the country was born and fought over, eager to make it into a land of opportunity. There’s a good reason that we’re likely to play those soundtracks in lieu of patriotic melodies. They fill us with pride and make us see not only the best in this country but in the world of theater’s ability to remind us of the value of telling these stories, buying into a mythology that defines us.

With that said, all I want to do this weekend is put on Assassins.

To back up, I’m not saying that I’m doing it as a greater statement, that it’s somehow more relevant than ever. If anything, the murdering of politicians is a plotline that will always be in poor taste no matter who is on the receiving end. 

However, Assassins is much more than a glorification of a violent subset of people. This isn’t a careless Joker (2019)-like commentary that says “everything sucks so why should I care?” Stephen Sondheim is incapable of making something with such a base-level commentary. What he’s done here is stared into the void of American history and asked us to question these men and women who thought that their only potential in life was to shoot a president. It’s not an embrace of masochism, even if we’re thrown into one of the darkest satires put onto the stage. It’s a cautionary story of a working-class unable to express themselves any other way.

As someone who enjoys collecting trivia about various different presidents, I found myself down a Wikipedia wormhole looking at various information. Somehow a tangent about Squeaky Fromme leads me to realize something that I couldn’t believe. How was there a musical where The Manson Family sang songs? Who would dare to make this mad group of people into characters that took in this great pastime of dancing across a stage like they’re in Oklahoma? It’s called… Assassins? What is even going on anymore?


I didn’t think of it much as a Sondheim work at the time. Had I done so, I probably would’ve recognized its deserving place as a spiritual sequel to Sweeney Todd: The Demon Barber of Fleet Street. Both focus on these murderous figures who become overwhelmed by their actions. I’d argue that Sweeney Todd is more sympathetic, allowing us to revel in Sondheim’s darkest, most twisted songbook ever. 

The big difference between the two is that one is the study of a man whereas the other takes a look at an entire country and its history. There has to be a reason that names like John Wilkes Booth, Lee Harvey Oswald, and John Hinckley Jr. have become footnotes of history, even if they’re the most notorious cautionary tales that you can have. We don’t remember them for their life stories. All we know is that they became ravaged with the obsession to kill a president. Who were these people and why did they do this?

The thing is that Assassins can’t help but exist inside of the phrase “morbid curiosity.” How couldn't it? This is a subject that would only be tackled by a sadomasochist… or a historian, your pick. Still, who would want to see a musical glorifying the darkest corners of humanity? I know that some people would easily embrace a show where the murderers are glorified as misunderstood heroes, but again that’s too easy for Sondheim.

To be honest, I want to call this one of his best, but when you have a career like his what does best even mean? If Assassins was your only credit, you’d be labeled a genius, capable of tapping into this country’s warped perception of The American Dream. People would be eager to see your next project, but alas Sondheim is someone with 30 years of masterpieces by the time this came along, serving as a satire so dark that I worry that it will only ever receive two reactions from audiences: disgust or think it’s a manifesto.

I can only speak to my experience with this show. Prior to COVID-19, I was going to see it for the second time this Fall. With that said, I saw it at The Long Beach Playhouse a few years back now and can honestly say that I regret not seeing it again. Maybe it just speaks to my tastes, but I wanted to study how the show handled this icky subject matter and made it so endearing without ever working as an endorsement. Much like its carnival setting, it’s a tightrope act that could go so wrong so quickly, and I’m amazed that what it does is make me understand the assassins’ perspective to a hypnotic degree while having to walk out feeling scared that I now see their reason a bit more clearly.


The story is presented through John Wilkes Booth. He could be called a narrator, or at least a cipher who exists throughout the many timelines. In the opening song “Everybody’s Got the Right,” he is seen standing in front of a shooter game with portraits of the various presidents lining the spectacle. As people pass, he hands out guns like a barker, asking if they want to kill a president. When put this way we’re exposed to this like a barker trying to get us to play a game. It trivializes the act to such a degree that it removes a layer of an uncomfortable reality. This can be construed as being from Booth’s perspective, where it’s all a game where everyone stands to win something. In every case, it’s infamy.

I love how unconventional the rest of the show feels. Even if it’s a chronological journey through these stories, they’re more vignettes that are meant to personalize each character’s struggle. Booth is our entry point because he’s the one who started this new trend. He infamously murdered Abraham Lincoln. We all know that story. To follow him as he hides from a force wishing to hang him, we’re presented in something tense and manipulative. Over the next song, he’s going to try and make us care about his reason.

Of course, this is where Sondheim’s bigger reason for taking on the project begins to shine through. For as perverse as Booths’ reasons for murdering Lincoln was, it removes something else from his legacy. Nobody will remember him as the great stage actor that he could’ve been. This is an entry point near and dear to Sondheim, as it reflects the effort to be something greater and years of effort become negated because one thing snapped in his brain. The fact that he’s the rational voice for most of the musical should tell you how things are going to go. He’s the ghost over every other character’s shoulder, almost taunting them to follow “that golden sight.” 

I won’t go into everyone else’s story, but it becomes clear what Assassins wants to achieve. It wants to answer why these people did what they did. Not everyone will have been successful in their plans, some ending in these comic misfires (no pun intended). Some are riled up in narcissism and delusion, others political persuasion by others. It’s a world where mental illness is taken seriously, throwing the audience into the appalling corners as we’re stuck with figures that have been neglected, talking themselves into a cynicism that is at very least ambitious. Not everyone will go through with their fantasies.


One of the most staggering, in a larger context, is Samuel Byck. He is the man who will fail to murder Richard M. Nixon, but whose story to that day is much more disturbing than that. Yes, somehow a man who will attempt to hijack a plane and crash it into The White House has had a crazier life leading up to it. As he sits on a park bench in a dirty Santa suit, he records messages to Leonard Bernstein. 

Yes, the same one you’re thinking of. Much like how Booth could be seen as playing on Sondheim’s love of theater, Byck’s choice to criticize his West Side Story collaborator so directly brings the show full circle. He sings “America” and claims that Bernstein is ignoring him. As far as self-referencing goes, this is high art that connects any fiction with reality in ways that make you understand how familiar these people are. They’re celebrity obsessed like we are, and who’s to say that Sondheim couldn’t have fallen victim to Byck’s wild misunderstanding of the world? While John Hinckley Jr. may get more credit for his Jodie Foster-stalking number “Unworthy of Your Love,” I think Byck’s West Side Story reference is much more haunting if you know your theater history. This is a musical composed by the lyricist for that show, and suddenly Booth feels painfully personal to Sondheim as an artist.

There’s a lot to love about where things go throughout this show, if just because it’s a survey of American history. Sondheim has said that it’s presented in the style of Americana, where there was a lot of marching band and turn of the century styles that informed patriotic music. The jauntiness works to hide the disturbing subtext, such as in “Another National Anthem,” which uses American signifiers like ballparks and mailmen winning the lottery to show ways that The Average Joe has experienced The American Dream. But, as these characters ask “Where’s my prize?” 


If you’re a person of reason, you should know that they don’t deserve a prize. If they deserve anything, it’s a psyche evaluation. It’s something that becomes front and center with a closing number based around Lee Harvey Oswald with “November 22, 1963.” Once again we’re thrown into a battle of demons as Booth convinces him that he needs to murder John F. Kennedy. It goes on, finally breaking the pageantry of the show and getting into this tense study. We all know that Oswald will never be more than a murderer. Considering that JFK will be the most notorious presidential murder of the 20th century, Oswald reaches a level of notoriety that only Booth seems to have. He’s kept the world from experiencing optimism and change. 

After all, Stephen King wrote a whole book about reversing the assassination. That’s how much this moment lingers.

On a quick tangent, I also love that “The Ballad of Czolgosz,” which turns the final days of Leon Czolgosz into a jaunty, upbeat country tune full of “I am going to the lordy!” The best/worst part, depending on your view? Sondheim claims that a lot of it was verbatim from the man’s account.

What do we get from being with these characters? It is a form of sympathy that is difficult to grapple with. Assassins looks at how these people helped to evade change, whether for themselves or America, forcing them to become notorious outlaws. These are topics that reflect things that were on some level preventable. Had these people lived different lives, gotten mental help that they needed, maybe they would be helped. Still, the way that Booth likes to see it is that it’s inevitable, a stain on America’s conscience that we’re all striving for that one achievement. It drives some of us mad, and we have to be aware of it. We can’t change until we accept that darkness and unforgivable sins are in the country’s DNA.

Assassins is a difficult narrative, and I admire it for wanting to be unpleasant. It uses is source material with a responsibility that could’ve easily gone wrong. It requires you to grapple with the thought, constantly as engrossed by the madness as you are horrified. Sondheim ties it to every aspect of American society, and in some ways makes it a critical study. It’s unpleasant and subversive but uses every element as more than a novelty. You come out feeling shocked that a story like this could work. 

I don’t want to play it this July 4 because of any personal feelings. Frankly, it all feels counterproductive to use it as any greater symbolism. I just love it as an example of why theater is essential, capable of telling stories that allow for some distance, where danger can’t hurt us. Assassins won’t always appeal to the masses nor do I think it should be embraced by true crime junkies. It’s more a story about our identity and what values it has to live in a land of competition if losing can result in so much pain. What are we striving for in this game? I don’t know that Assassins answers that question, but it works as one of the greatest cautionary tales that need occasional reminding.

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