Tossing aside its usual family fare, the Cottage Theatre reaches for something darker in its current production of Stephen Sondheim’s Assassins.

“Angry men don’t write the rules,” sings the infamous John Wilkes Booth, ably played by Kory Weimer, “and guns don’t right the wrongs.”

Booth is just one of nine assassins who have their day in this 1990 musical, with music and lyrics by Stephen Sondheim and songbook by John Weidman.

Tracing America’s violent past, Assassins trains its crosshairs on nine people throughout U.S. history who all share one thing in common: Each of them has attempted to assassinate a president of the United States. Under direction by Tony Rust, Assassins explores the depths of shared psychosis, searching for motivation within the inexplicable actions of this imagined criminal brotherhood.

“What a wonder is a gun! What a versatile invention!” sings Leon Czolgosz, an immigrant steel mill worker responsible for the assassination of William McKinley, played with quiet restraint by Ward Fairbairn. The most successful performances, like Fairbairn’s, are temperate enough to draw us in, allowing us to reluctantly empathize with these raw, broken people.

We’re introduced to John Hinkley Jr., Ronald Reagan’s would-be killer, depicted with eerie awkwardness by Austin VanderPlaat, and to Charles J. Guiteau, an American preacher, writer and lawyer convicted of assassinating President James Garfield, who pulses with revivalist fervor from actor George Comstock. Tracy Nygard delivers a hauntingly believable Sara Jane Moore, one of Charles Manson’s cult followers, who attempts to take the life of Gerald Ford.

Dale Flynn exudes pathos as Samuel Byck, an unemployed salesman who wants to kill Richard Nixon. Dressed in a tattered Santa suit, Byck opines into a tape recorder, leaving a message for Leonard Bernstein about how he misses the innocence of early musicals, songs like “Tonight” from West Side Story.

Written in 1955, West Side Story partnered Bernstein and Sondheim in an unparalleled artistic fusion. But there’s something more to the reference here, a longing for a simpler time. Sondheim was 33 when John F. Kennedy was shot, and as Assassins churns forward and the rogue’s gallery of assassins accumulates, there’s a sinking feeling in the audience that someone is missing. No spoilers, but things heat up, perhaps uncomfortably so.

Live music under the direction of Jim Greenwood is consistently first rate. And throughout, Lanny Mitchell as the Balladeer offers a soothing counterpoint to all the vitriol. With voice and mannerisms both natural and compelling, Mitchell gently guides the viewer through uncharted waters.

Assassins runs through Oct. 19 at the Cottage Theatre, 700 Village Dr., Cottage Grove; $19-$23.