Something seems off about Abraham Lincoln’s presidential box. Tattered curtains hang above a broken picture frame of George Washington, surrounded by the faded colors of Old Glory. It’s a haunting reminder of one of the darkest chapters in American history. However, we’re not exactly sitting at Ford’s Theatre, where the 16th president was killed by an actor during a performance of “Our American Cousin” in April 1865.

In “Assassins,” Signature Theatre takes audiences on a roller coaster through history—beginning with Lincoln shooter John Wilkes Booth, one of many notorious historical figures in this Sondheim musical. This is Signature’s third time presenting this Tony-winning work, which kicks off its 30th season.

Like the fairy tale mashup, “Into the Woods,” which brought together beloved characters from children’s literature, this revue-styled show has nine successful and not-so-successful assassins sharing the stage as they each get their shot to tell their stories. There’s even an amusing bar scene where they’re all just hanging out, drinking their beverage of choice: Coke, Tab or a glass of milk in the case of Giuseppe Zangara, the firecracker Italian immigrant with tummy issues who attempted to kill FDR.

Bookwriter John Weidman gives a voice to these misfits as they reveal their political and personal motivations behind their actions, whether it’s dissatisfaction with the government or taking a stand against social inequality or to attract the attention of a young Hollywood starlet. The musical, based on an idea by Charles Gilbert Jr., profiles assassins through the ages from “pioneer” Booth all the way to Lee Harvey Oswald as it explores the dark side of the American dream.

“Assassins” is a daring piece of musical theater, given the subject matter, and offers plenty of discomforting and delightful moments. Ian McEuen as Zangara is a terrifying presence in the musical number “How I Saved Roosevelt,” shouting from the electric chair while a group of bystanders nearby joyfully recount their heroic actions for the press. (“I saw right away he was insane / Oh, this is my husband, we’re from Maine” is a favorite line from this song.) And in the jaunty gospel-tinged “The Ballad of Guiteau,” the author/lawyer responsible for Garfield’s death is singing and dancing his way upstairs to the gallows—complete with hand clapping and high kicks. Eventually, the dark humor present throughout much of the musical subsides as it nears the chilling final moments when it becomes Oswald’s turn. Sam Ludwig, who also plays the Balladeer, the optimistic narrator, is especially moving as Oswald, who struggles to pull the trigger as the assassins surround him.

With impeccable direction from Eric Schaeffer, “Assassins” is loaded with powerful performances, which provide a glimpse into these criminal minds. As Booth, Vincent Kempski is absolutely magnetic in his portrayal of the Confederate sympathizer who fiercely believes Lincoln was a tyrant and killed the country, provoking a war that cost the lives of hundreds of thousands. Pale-faced with haunting eyes, Booth stands out in this lineup, paving the way for others who changed history with a single little finger.

Other standouts include a cheery performance by Bobby Smith as the book-hawking Charles Guiteau, who dreams of becoming the ambassador to France; and the comedic pairing of Tracy Lynn Olivera as the trigger-happy mother Sara Jane Moore and Rachel Zampelli as laid-back hippie Lynette “Squeaky” Fromme, who bond over their connection to cult leader Charles Manson and fail miserably to off Gerald Ford when he’s right in front of their faces.

“Assassins” is a stirring and entertaining exploration of what drove these troubled characters to make their marks on history.

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